diff --git a/Journal.AI/Coach-Rules.txt b/Journal.AI/Coach-Rules.txt
new file mode 100644
index 0000000..b65dc90
--- /dev/null
+++ b/Journal.AI/Coach-Rules.txt
@@ -0,0 +1,35 @@
+You are a personal coach inside a private journaling app.
+Your goals:
+- Be supportive, practical, and brief.
+- Ask at most {{maxQuestions}} questions.
+- Suggest at most {{maxNextActions}} next actions.
+- Default to small, realistic steps.
+
+Hard rules:
+- Do not diagnose medical or mental health conditions.
+- Do not use shame, guilt, or alarmist language.
+- Do not claim certainty about the user's feelings or motives.
+- Treat all suggestions as optional proposals.
+- Output MUST be a single valid JSON object with NO text before or after it.
+- Do NOT output explanations, templates, or examples — only the final JSON.
+- If context is missing, make gentle assumptions and ask 1 clarifying question.
+
+Evidence:
+- When making an observation or suggestion, include evidence snippets with recordId when available.
+
+You MUST respond with a single valid JSON object. No text before or after the JSON.
+
+Required JSON schema:
+{
+  "kind": "daily_checkin" | "evening_review" | "weekly_review",
+  "title": "<short title>",
+  "summary": "<2-4 sentence summary>",
+  "questions": ["<question>"],
+  "suggestedNextActions": ["<action>"],
+  "suggestedTags": ["<tag>"],
+  "evidence": [{"recordId": null, "text": "<snippet>"}],
+  "patchProposal": null
+}
+The top-level "kind" MUST be exactly one of: "daily_checkin", "evening_review", "weekly_review".
+Set patchProposal to null unless a draft is clearly helpful. If needed use: {"kind": "createDraft", "description": "<why>", "content": "<markdown>"}.
+Do NOT confuse patchProposal.kind with the top-level kind field.
diff --git a/Journal.AI/Daily-Check-In.txt b/Journal.AI/Daily-Check-In.txt
new file mode 100644
index 0000000..c879030
--- /dev/null
+++ b/Journal.AI/Daily-Check-In.txt
@@ -0,0 +1,20 @@
+{{CoachRules}}
+
+Task:
+Generate a DAILY CHECK-IN plan for date {{dateLocal}}.
+
+Context (JSON):
+{{contextJson}}
+
+Preferences (JSON):
+{{preferencesJson}}
+
+Output:
+Return a CoachPlanDto JSON with kind="daily_checkin".
+Include:
+- A short title
+- A 2-4 sentence summary
+- 1-{{maxQuestions}} questions
+- 1-{{maxNextActions}} suggestedNextActions
+- suggestedTags if relevant
+- patchProposal that creates a fragment or dailyEntry draft ONLY if it is clearly helpful.
\ No newline at end of file
diff --git a/Journal.AI/Evening-Review.txt b/Journal.AI/Evening-Review.txt
new file mode 100644
index 0000000..788198e
--- /dev/null
+++ b/Journal.AI/Evening-Review.txt
@@ -0,0 +1,19 @@
+{{CoachRules}}
+
+Task:
+Generate an EVENING REVIEW for date {{dateLocal}}.
+
+Context (JSON):
+{{contextJson}}
+
+Preferences (JSON):
+{{preferencesJson}}
+
+Output:
+Return a CoachPlanDto JSON with kind="evening_review".
+Include:
+- Brief recap of today
+- 2-4 observations with evidence
+- 1-{{maxQuestions}} reflection questions
+- 1-{{maxNextActions}} next actions for tomorrow
+- patchProposal that creates: (optional) tomorrow-intent fragment AND/OR todos.
\ No newline at end of file
diff --git a/Journal.AI/Journal.AI.csproj b/Journal.AI/Journal.AI.csproj
new file mode 100644
index 0000000..97186d9
--- /dev/null
+++ b/Journal.AI/Journal.AI.csproj
@@ -0,0 +1,25 @@
+<Project Sdk="Microsoft.NET.Sdk">
+
+  <PropertyGroup>
+    <TargetFramework>net10.0</TargetFramework>
+    <ImplicitUsings>enable</ImplicitUsings>
+    <Nullable>enable</Nullable>
+  </PropertyGroup>
+
+  <ItemGroup>
+    <PackageReference Include="LLamaSharp" Version="0.26.0" />
+    <PackageReference Include="LLamaSharp.Backend.Cpu" Version="0.26.0" />
+  </ItemGroup>
+
+  <ItemGroup>
+    <ProjectReference Include="..\Journal.Core\Journal.Core.csproj" />
+  </ItemGroup>
+
+  <ItemGroup>
+    <EmbeddedResource Include="Coach-Rules.txt" />
+    <EmbeddedResource Include="Daily-Check-In.txt" />
+    <EmbeddedResource Include="Evening-Review.txt" />
+    <EmbeddedResource Include="Weekly-Review.txt" />
+  </ItemGroup>
+
+</Project>
diff --git a/Journal.AI/LlamaSharpAiService.cs b/Journal.AI/LlamaSharpAiService.cs
new file mode 100644
index 0000000..5827f28
--- /dev/null
+++ b/Journal.AI/LlamaSharpAiService.cs
@@ -0,0 +1,336 @@
+using System.Text;
+using System.Text.RegularExpressions;
+using Journal.Core.Dtos;
+using Journal.Core.Models;
+using Journal.Core.Services.Ai;
+using LLama;
+using LLama.Common;
+using LLama.Sampling;
+
+namespace Journal.AI;
+
+public sealed partial class LlamaSharpAiService(JournalConfig config) : IAiService, IDisposable
+{
+    private const string DefaultModelUrl =
+        "https://huggingface.co/microsoft/Phi-3-mini-4k-instruct-gguf/resolve/main/Phi-3-mini-4k-instruct-q4.gguf";
+    private const string DefaultModelFileName = "Phi-3-mini-4k-instruct-q4.gguf";
+    private const string ModelSubDirectory = "ai-models";
+
+    private readonly string _configuredModelPath = config.GgufModelPath;
+    private readonly uint _contextSize = (uint)Math.Clamp(config.ModelContextTokens, 512, 4096);
+    private readonly int _gpuLayers = config.LlamaCppTimeout;
+
+    private readonly Lock _sync = new();
+    private string? _resolvedModelPath;
+    private LLamaWeights? _weights;
+    private bool _disposed;
+
+    public Task<AiHealthDto> HealthAsync(CancellationToken cancellationToken = default)
+    {
+        var resolved = _resolvedModelPath ?? _configuredModelPath;
+        var modelExists = File.Exists(resolved) || File.Exists(GetDefaultModelPath());
+        var loaded = _weights is not null;
+        return Task.FromResult(new AiHealthDto(
+            Provider: "llamasharp",
+            Enabled: true,
+            Healthy: modelExists || loaded,
+            Message: loaded
+                ? "Model loaded."
+                : modelExists
+                    ? "Model found (will load on first use)."
+                    : "Model not found locally. It will be downloaded on first use."));
+    }
+
+    private static string BuildChatSystemPrompt()
+    {
+        var dateStr = DateTime.Now.ToString("MMMM d, yyyy");
+        return $"You are a supportive conversational coach inside a private journaling app. " +
+               $"Today's date is {dateStr}. " +
+               $"Reply in plain natural language only. Never output JSON, code blocks, or structured data. " +
+               $"Be warm, practical, and concise. Do not repeat yourself.";
+    }
+
+    public async Task<string> ChatAsync(string prompt, CancellationToken cancellationToken = default)
+    {
+        if (string.IsNullOrWhiteSpace(prompt))
+            throw new ArgumentException("Prompt is required.", nameof(prompt));
+
+        var raw = await RunSessionAsync(prompt, BuildChatSystemPrompt(),
+            maxTokens: 512, cancellationToken: cancellationToken);
+        return CleanChatResponse(raw);
+    }
+
+    public async Task<string> ChatWithHistoryAsync(IReadOnlyList<(string Role, string Text)> history,
+        string prompt, CancellationToken cancellationToken = default)
+    {
+        if (string.IsNullOrWhiteSpace(prompt))
+            throw new ArgumentException("Prompt is required.", nameof(prompt));
+
+        var modelPath = await EnsureModelAsync(cancellationToken);
+        EnsureWeights(modelPath);
+
+        using var context = _weights!.CreateContext(new ModelParams(modelPath)
+        {
+            ContextSize = _contextSize,
+            GpuLayerCount = _gpuLayers
+        });
+
+        var executor = new StatelessExecutor(_weights!, context.Params);
+
+        // Build multi-turn Phi-3 prompt with full conversation history
+        var sb = new StringBuilder();
+        sb.Append($"<|system|>\n{BuildChatSystemPrompt()}<|end|>\n");
+
+        foreach (var (role, text) in history)
+        {
+            var tag = string.Equals(role, "user", StringComparison.OrdinalIgnoreCase) ? "user" : "assistant";
+            sb.Append($"<|{tag}|>\n{text}<|end|>\n");
+        }
+
+        sb.Append($"<|user|>\n{prompt}<|end|>\n");
+        sb.Append("<|assistant|>\n");
+
+        var inferenceParams = new InferenceParams
+        {
+            MaxTokens = 512,
+            AntiPrompts = ["<|user|>", "<|system|>", "<|end|>", "<|endoftext|>"],
+            SamplingPipeline = new DefaultSamplingPipeline { Temperature = 0.7f }
+        };
+
+        var result = new StringBuilder();
+        await foreach (var token in executor.InferAsync(sb.ToString(), inferenceParams, cancellationToken))
+        {
+            result.Append(token);
+        }
+
+        return CleanChatResponse(StripSpecialTokens(result.ToString()));
+    }
+
+    internal async Task<string> ChatJsonAsync(string prompt, CancellationToken cancellationToken = default)
+    {
+        if (string.IsNullOrWhiteSpace(prompt))
+            throw new ArgumentException("Prompt is required.", nameof(prompt));
+
+        var dateStr = DateTime.Now.ToString("MMMM d, yyyy");
+        return await RunSessionAsync(prompt,
+            $"You are a coaching assistant inside a private journaling app. " +
+            $"Today's date is {dateStr}. " +
+            $"You MUST respond with a single valid JSON object. No text before or after the JSON.",
+            maxTokens: 1024, cancellationToken: cancellationToken);
+    }
+
+    public async Task<string> SummarizeEntryAsync(string content, string? fileStem = null,
+        CancellationToken cancellationToken = default)
+    {
+        if (string.IsNullOrWhiteSpace(content))
+            throw new ArgumentException("Entry content is required.", nameof(content));
+
+        var prompt = fileStem is not null
+            ? $"Summarize this journal entry ({fileStem}) concisely:\n\n{content}"
+            : $"Summarize this journal entry concisely:\n\n{content}";
+
+        return await ChatAsync(prompt, cancellationToken);
+    }
+
+    public async Task<string> SummarizeAllAsync(IReadOnlyList<string> entries,
+        CancellationToken cancellationToken = default)
+    {
+        if (entries is null || entries.Count == 0)
+            return "No entries to summarize.";
+
+        var combined = string.Join("\n\n---\n\n", entries);
+        var prompt = $"Summarize the following {entries.Count} journal entries into a concise overview:\n\n{combined}";
+
+        return await ChatAsync(prompt, cancellationToken);
+    }
+
+    public async Task<IReadOnlyList<double>> EmbedAsync(string content,
+        CancellationToken cancellationToken = default)
+    {
+        if (string.IsNullOrWhiteSpace(content))
+            throw new ArgumentException("Content is required.", nameof(content));
+
+        var modelPath = await EnsureModelAsync(cancellationToken);
+
+        try
+        {
+            EnsureWeights(modelPath);
+            var embedder = new LLamaEmbedder(_weights!, new ModelParams(modelPath)
+            {
+                Embeddings = true,
+                ContextSize = _contextSize,
+                GpuLayerCount = _gpuLayers
+            });
+
+            var embeddingArrays = await embedder.GetEmbeddings(content, cancellationToken);
+            var result = new List<double>();
+
+            foreach (var arr in embeddingArrays)
+            {
+                foreach (var val in arr)
+                {
+                    result.Add(val);
+                }
+            }
+
+            return result;
+        }
+        catch
+        {
+            return [];
+        }
+    }
+
+    // ── Model download (mirrors LocalWhisperS2TService.EnsureModelAsync) ───
+
+    private static string GetDefaultModelPath()
+    {
+        var modelDirectory = Path.Combine(
+            Environment.GetFolderPath(Environment.SpecialFolder.LocalApplicationData),
+            "ProjectJournal",
+            ModelSubDirectory);
+        return Path.Combine(modelDirectory, DefaultModelFileName);
+    }
+
+    private async Task<string> EnsureModelAsync(CancellationToken cancellationToken = default)
+    {
+        // 1. Configured path takes priority if the file already exists
+        if (File.Exists(_configuredModelPath))
+            return _configuredModelPath;
+
+        // 2. Check the standard app-data location
+        var defaultPath = GetDefaultModelPath();
+        if (File.Exists(defaultPath))
+            return defaultPath;
+
+        // 3. Download from HuggingFace
+        var modelDirectory = Path.GetDirectoryName(defaultPath)!;
+        Directory.CreateDirectory(modelDirectory);
+
+        var tempPath = defaultPath + ".download";
+        using var cts = CancellationTokenSource.CreateLinkedTokenSource(cancellationToken);
+        cts.CancelAfter(TimeSpan.FromMinutes(30));
+
+        using var httpClient = new HttpClient();
+        httpClient.Timeout = TimeSpan.FromMinutes(30);
+
+        using var response = await httpClient.GetAsync(DefaultModelUrl,
+            HttpCompletionOption.ResponseHeadersRead, cts.Token);
+        response.EnsureSuccessStatusCode();
+
+        await using var contentStream = await response.Content.ReadAsStreamAsync(cts.Token);
+        await using var fileStream = new FileStream(tempPath, FileMode.Create, FileAccess.Write, FileShare.None);
+        await contentStream.CopyToAsync(fileStream, cts.Token);
+        await fileStream.FlushAsync(cts.Token);
+        fileStream.Close();
+
+        File.Move(tempPath, defaultPath, overwrite: true);
+        return defaultPath;
+    }
+
+    // ── Session / weights lifecycle ────────────────────────────────────────
+
+    private async Task<string> RunSessionAsync(string prompt, string systemPrompt,
+        int maxTokens, CancellationToken cancellationToken)
+    {
+        var modelPath = await EnsureModelAsync(cancellationToken);
+        EnsureWeights(modelPath);
+
+        // Fresh context per call — prevents KV cache accumulation across requests
+        using var context = _weights!.CreateContext(new ModelParams(modelPath)
+        {
+            ContextSize = _contextSize,
+            GpuLayerCount = _gpuLayers
+        });
+
+        // Use StatelessExecutor with explicit Phi-3 chat template so the model
+        // never sees raw system text it can echo back to the user.
+        var executor = new StatelessExecutor(_weights!, context.Params);
+
+        var fullPrompt = $"<|system|>\n{systemPrompt}<|end|>\n" +
+                         $"<|user|>\n{prompt}<|end|>\n" +
+                         $"<|assistant|>\n";
+
+        var inferenceParams = new InferenceParams
+        {
+            MaxTokens = maxTokens,
+            AntiPrompts = [
+                "<|user|>",
+                "<|system|>",
+                "<|end|>",
+                "<|endoftext|>",
+            ],
+            SamplingPipeline = new DefaultSamplingPipeline
+            {
+                Temperature = 0.7f
+            }
+        };
+
+        var sb = new StringBuilder();
+
+        await foreach (var token in executor.InferAsync(fullPrompt, inferenceParams, cancellationToken))
+        {
+            sb.Append(token);
+        }
+
+        return StripSpecialTokens(sb.ToString());
+    }
+
+    /// <summary>Strips only Phi-3 special tokens — safe for JSON output.</summary>
+    private static string StripSpecialTokens(string raw)
+    {
+        var text = raw;
+        foreach (var marker in new[] { "<|assistant|>", "<|user|>", "<|system|>", "<|end|>", "<|endoftext|>" })
+            text = text.Replace(marker, "");
+        return text.Trim();
+    }
+
+    // Matches role labels like "System:", "**System:**", "**Assistant:**", "User:" etc.
+    private static readonly Regex RoleMarkerRegex = MyRegex();
+
+    /// <summary>Aggressive cleanup for conversational (non-JSON) responses.</summary>
+    private static string CleanChatResponse(string raw)
+    {
+        var text = StripSpecialTokens(raw);
+
+        // Strip role markers in any formatting variant (plain, bold-markdown, etc.)
+        text = RoleMarkerRegex.Replace(text, "");
+
+        // Remove orphaned bold markers left behind after stripping
+        text = text.Replace("**", "");
+
+        // Collapse runs of 3+ newlines into 2
+        text = Regex.Replace(text, @"\n{3,}", "\n\n");
+
+        return text.Trim();
+    }
+
+    private void EnsureWeights(string modelPath)
+    {
+        if (_weights is not null) return;
+
+        lock (_sync)
+        {
+            if (_weights is not null) return;
+
+            _resolvedModelPath = modelPath;
+            _weights = LLamaWeights.LoadFromFile(new ModelParams(modelPath)
+            {
+                ContextSize = _contextSize,
+                GpuLayerCount = _gpuLayers
+            });
+        }
+    }
+
+    public void Dispose()
+    {
+        if (_disposed) return;
+        _disposed = true;
+        _weights?.Dispose();
+    }
+
+    [GeneratedRegex(@"\*{0,2}(System|Assistant|User):\*{0,2}", RegexOptions.IgnoreCase | RegexOptions.Compiled, "en-US")]
+    private static partial Regex MyRegex();
+    [GeneratedRegex(@"\n{3,}")]
+    private static partial Regex MyRegex1();
+}
diff --git a/Journal.AI/LlamaSharpCoachService.cs b/Journal.AI/LlamaSharpCoachService.cs
new file mode 100644
index 0000000..5e17f02
--- /dev/null
+++ b/Journal.AI/LlamaSharpCoachService.cs
@@ -0,0 +1,181 @@
+using System.Reflection;
+using System.Text;
+using System.Text.Json;
+using Journal.Core.Dtos;
+using Journal.Core.Services.Ai;
+
+namespace Journal.AI;
+
+public sealed class LlamaSharpCoachService(LlamaSharpAiService ai) : ICoachService
+{
+    private static readonly JsonSerializerOptions JsonOptions = new()
+    {
+        PropertyNameCaseInsensitive = true
+    };
+
+    private readonly LlamaSharpAiService _ai = ai;
+    private readonly string _coachRules = LoadEmbeddedResource("Coach-Rules.txt");
+    private readonly string _dailyTemplate = LoadEmbeddedResource("Daily-Check-In.txt");
+    private readonly string _eveningTemplate = LoadEmbeddedResource("Evening-Review.txt");
+    private readonly string _weeklyTemplate = LoadEmbeddedResource("Weekly-Review.txt");
+
+    public async Task<CoachPlanDto> DailyCheckInAsync(CoachContextDto context,
+        CancellationToken cancellationToken = default)
+    {
+        var prefs = context.Preferences ?? new CoachPreferencesDto();
+        var prompt = InterpolateTemplate(_dailyTemplate, context, prefs);
+        return await RunCoachPromptAsync(prompt, "daily_checkin", cancellationToken);
+    }
+
+    public async Task<CoachPlanDto> EveningReviewAsync(CoachContextDto context,
+        CancellationToken cancellationToken = default)
+    {
+        var prefs = context.Preferences ?? new CoachPreferencesDto();
+        var prompt = InterpolateTemplate(_eveningTemplate, context, prefs);
+        return await RunCoachPromptAsync(prompt, "evening_review", cancellationToken);
+    }
+
+    public async Task<CoachPlanDto> WeeklyReviewAsync(CoachContextDto context,
+        CancellationToken cancellationToken = default)
+    {
+        var prefs = context.Preferences ?? new CoachPreferencesDto();
+        var prompt = InterpolateTemplate(_weeklyTemplate, context, prefs);
+        return await RunCoachPromptAsync(prompt, "weekly_review", cancellationToken);
+    }
+
+    private async Task<CoachPlanDto> RunCoachPromptAsync(string prompt, string fallbackKind,
+        CancellationToken cancellationToken)
+    {
+        var raw = await _ai.ChatJsonAsync(prompt, cancellationToken);
+
+        // Try to extract JSON from the response
+        var json = ExtractJson(raw);
+        if (json is not null)
+        {
+            try
+            {
+                var parsed = JsonSerializer.Deserialize<CoachPlanDto>(json, JsonOptions);
+                if (parsed is not null)
+                    return parsed with { Kind = fallbackKind };
+            }
+            catch (JsonException)
+            {
+                // Fall through to fallback
+            }
+        }
+
+        // Fallback: wrap raw text into a CoachPlanDto
+        return new CoachPlanDto(
+            Kind: fallbackKind,
+            Title: "Coach Response",
+            Summary: raw,
+            Questions: [],
+            SuggestedNextActions: [],
+            SuggestedTags: [],
+            Evidence: []);
+    }
+
+    private string InterpolateTemplate(string template, CoachContextDto context, CoachPreferencesDto prefs)
+    {
+        var contextJson = JsonSerializer.Serialize(new
+        {
+            recentEntries = context.RecentEntries ?? [],
+            recentFragments = context.RecentFragments ?? []
+        });
+
+        var preferencesJson = JsonSerializer.Serialize(new
+        {
+            prefs.MaxQuestions,
+            prefs.MaxNextActions
+        });
+
+        var result = template
+            .Replace("{{CoachRules}}", _coachRules)
+            .Replace("{{dateLocal}}", context.DateLocal)
+            .Replace("{{weekStartLocal}}", context.WeekStartLocal ?? "")
+            .Replace("{{weekEndLocal}}", context.WeekEndLocal ?? "")
+            .Replace("{{contextJson}}", contextJson)
+            .Replace("{{preferencesJson}}", preferencesJson)
+            .Replace("{{maxQuestions}}", prefs.MaxQuestions.ToString())
+            .Replace("{{maxNextActions}}", prefs.MaxNextActions.ToString());
+
+        return result;
+    }
+
+    private static string? ExtractJson(string text)
+    {
+        // 1. Try ```json ... ``` code block
+        var codeBlockStart = text.IndexOf("```json", StringComparison.Ordinal);
+        if (codeBlockStart >= 0)
+        {
+            var jsonStart = text.IndexOf('{', codeBlockStart);
+            var codeBlockEnd = text.IndexOf("```", codeBlockStart + 7, StringComparison.Ordinal);
+            if (jsonStart >= 0 && codeBlockEnd > jsonStart)
+            {
+                var candidate = text[jsonStart..codeBlockEnd].Trim();
+                if (TryValidateJson(candidate))
+                    return candidate;
+            }
+        }
+
+        // 2. Look specifically for {"kind" — the expected first field of CoachPlanDto
+        var kindMarker = text.IndexOf("{\"kind\"", StringComparison.Ordinal);
+        if (kindMarker < 0)
+            kindMarker = text.IndexOf("{ \"kind\"", StringComparison.Ordinal);
+        if (kindMarker >= 0)
+        {
+            var lastBrace = text.LastIndexOf('}');
+            if (lastBrace > kindMarker)
+            {
+                var candidate = text[kindMarker..(lastBrace + 1)];
+                if (TryValidateJson(candidate))
+                    return candidate;
+            }
+        }
+
+        // 3. Fallback: try each { position until one parses as valid JSON
+        var searchFrom = 0;
+        var globalLastBrace = text.LastIndexOf('}');
+        while (searchFrom < text.Length && globalLastBrace > searchFrom)
+        {
+            var bracePos = text.IndexOf('{', searchFrom);
+            if (bracePos < 0 || bracePos >= globalLastBrace)
+                break;
+
+            var candidate = text[bracePos..(globalLastBrace + 1)];
+            if (TryValidateJson(candidate))
+                return candidate;
+
+            searchFrom = bracePos + 1;
+        }
+
+        return null;
+    }
+
+    private static bool TryValidateJson(string json)
+    {
+        try
+        {
+            using var doc = JsonDocument.Parse(json);
+            return doc.RootElement.ValueKind == JsonValueKind.Object;
+        }
+        catch
+        {
+            return false;
+        }
+    }
+
+    private static string LoadEmbeddedResource(string fileName)
+    {
+        var assembly = Assembly.GetExecutingAssembly();
+        var resourceName = assembly.GetManifestResourceNames()
+            .FirstOrDefault(n => n.EndsWith(fileName, StringComparison.OrdinalIgnoreCase));
+
+        if (resourceName is null)
+            throw new FileNotFoundException($"Embedded resource not found: {fileName}");
+
+        using var stream = assembly.GetManifestResourceStream(resourceName)!;
+        using var reader = new StreamReader(stream, Encoding.UTF8);
+        return reader.ReadToEnd().Trim();
+    }
+}
diff --git a/Journal.AI/ServiceCollectionExtensions.cs b/Journal.AI/ServiceCollectionExtensions.cs
new file mode 100644
index 0000000..a8a40cb
--- /dev/null
+++ b/Journal.AI/ServiceCollectionExtensions.cs
@@ -0,0 +1,73 @@
+using Journal.Core.Services.Ai;
+using Journal.Core.Services.Config;
+using Journal.Core.Services.Sidecar;
+using Microsoft.Extensions.DependencyInjection;
+
+namespace Journal.AI;
+
+public static class ServiceCollectionExtensions
+{
+    /// <summary>
+    /// Registers LLamaSharp-based AI and Coach services.
+    /// Call this AFTER <c>AddFragmentServices()</c> so that <c>IJournalConfigService</c> is available.
+    /// When the provider is "llamasharp", this replaces the default <c>IAiService</c> registration.
+    /// </summary>
+    public static IServiceCollection AddLlamaSharpServices(this IServiceCollection services)
+    {
+        // Override IAiService — last registration wins in MS DI
+        services.AddSingleton<IAiService>(provider =>
+        {
+            var config = provider.GetRequiredService<IJournalConfigService>().Current;
+
+            if (string.Equals(config.AiProvider, "llamasharp", StringComparison.OrdinalIgnoreCase))
+            {
+                try
+                {
+                    return new LlamaSharpAiService(config);
+                }
+                catch (Exception ex)
+                {
+                    return new DisabledAiService(
+                        provider: "llamasharp",
+                        message: $"LLamaSharp unavailable: {ex.Message}",
+                        healthy: false);
+                }
+            }
+
+            if (string.Equals(config.AiProvider, "python-sidecar", StringComparison.OrdinalIgnoreCase))
+            {
+                try
+                {
+                    return new PythonSidecarAiService(config);
+                }
+                catch (Exception ex)
+                {
+                    return new DisabledAiService(
+                        provider: "python-sidecar",
+                        message: $"Python AI sidecar unavailable: {ex.Message}",
+                        healthy: false);
+                }
+            }
+
+            return new DisabledAiService(config.AiProvider);
+        });
+
+        // Register coach service
+        services.AddSingleton<ICoachService>(provider =>
+        {
+            var config = provider.GetRequiredService<IJournalConfigService>().Current;
+            var ai = provider.GetRequiredService<IAiService>();
+
+            if (ai is LlamaSharpAiService llamaAi)
+                return new LlamaSharpCoachService(llamaAi);
+
+            if (string.Equals(config.AiProvider, "none", StringComparison.OrdinalIgnoreCase))
+                return new DisabledCoachService();
+
+            return new DisabledCoachService(
+                $"Coach requires llamasharp provider (current: {config.AiProvider}).");
+        });
+
+        return services;
+    }
+}
diff --git a/Journal.AI/Weekly-Review.txt b/Journal.AI/Weekly-Review.txt
new file mode 100644
index 0000000..8e1c52a
--- /dev/null
+++ b/Journal.AI/Weekly-Review.txt
@@ -0,0 +1,19 @@
+{{CoachRules}}
+
+Task:
+Generate a WEEKLY REVIEW for {{weekStartLocal}} to {{weekEndLocal}}.
+
+Context (JSON):
+{{contextJson}}
+
+Preferences (JSON):
+{{preferencesJson}}
+
+Output:
+Return a CoachPlanDto JSON with kind="weekly_review".
+Include:
+- Themes (top 2-4) and blockers (top 1-3)
+- Wins (top 1-3)
+- 1-{{maxQuestions}} questions to set next week’s focus
+- 2-{{maxNextActions}} suggestedNextActions
+- patchProposal should only propose creating todos or a planning fragment, not editing old entries.
\ No newline at end of file
diff --git a/Journal.App/src/lib/backend/ai.ts b/Journal.App/src/lib/backend/ai.ts
new file mode 100644
index 0000000..0614287
--- /dev/null
+++ b/Journal.App/src/lib/backend/ai.ts
@@ -0,0 +1,222 @@
+import { sendCommand } from "./client";
+import { pickCase } from "./normalize";
+
+// ── Public types ────────────────────────────────────────────────
+
+export type AiHealthDto = {
+  provider: string;
+  enabled: boolean;
+  healthy: boolean;
+  message: string;
+};
+
+export type CoachEvidenceDto = {
+  recordId: string | null;
+  text: string;
+};
+
+export type CoachPatchProposalDto = {
+  kind: string;
+  description: string | null;
+  content: string | null;
+};
+
+export type CoachPlanDto = {
+  kind: string;
+  title: string;
+  summary: string;
+  questions: string[];
+  suggestedNextActions: string[];
+  suggestedTags: string[];
+  evidence: CoachEvidenceDto[];
+  patchProposal: CoachPatchProposalDto | null;
+};
+
+export type CoachPreferencesDto = {
+  maxQuestions?: number;
+  maxNextActions?: number;
+};
+
+export type CoachSessionPayload = {
+  dateLocal?: string;
+  weekStartLocal?: string;
+  weekEndLocal?: string;
+  recentEntries?: string[];
+  recentFragments?: string[];
+  preferences?: CoachPreferencesDto;
+};
+
+// ── Raw (PascalCase) variants for normalization ─────────────────
+
+type AiHealthDtoRaw = {
+  provider?: string;
+  enabled?: boolean;
+  healthy?: boolean;
+  message?: string;
+  Provider?: string;
+  Enabled?: boolean;
+  Healthy?: boolean;
+  Message?: string;
+};
+
+type CoachEvidenceDtoRaw = {
+  recordId?: string | null;
+  text?: string;
+  RecordId?: string | null;
+  Text?: string;
+};
+
+type CoachPatchProposalDtoRaw = {
+  kind?: string;
+  description?: string | null;
+  content?: string | null;
+  Kind?: string;
+  Description?: string | null;
+  Content?: string | null;
+};
+
+type CoachPlanDtoRaw = {
+  kind?: string;
+  title?: string;
+  summary?: string;
+  questions?: string[];
+  suggestedNextActions?: string[];
+  suggestedTags?: string[];
+  evidence?: CoachEvidenceDtoRaw[];
+  patchProposal?: CoachPatchProposalDtoRaw | null;
+  Kind?: string;
+  Title?: string;
+  Summary?: string;
+  Questions?: string[];
+  SuggestedNextActions?: string[];
+  SuggestedTags?: string[];
+  Evidence?: CoachEvidenceDtoRaw[];
+  PatchProposal?: CoachPatchProposalDtoRaw | null;
+};
+
+// ── Normalizers ─────────────────────────────────────────────────
+
+function normalizeHealth(raw: AiHealthDtoRaw): AiHealthDto {
+  return {
+    provider: pickCase(raw, "provider", "Provider", ""),
+    enabled: pickCase(raw, "enabled", "Enabled", false),
+    healthy: pickCase(raw, "healthy", "Healthy", false),
+    message: pickCase(raw, "message", "Message", ""),
+  };
+}
+
+function normalizeEvidence(raw: CoachEvidenceDtoRaw): CoachEvidenceDto {
+  return {
+    recordId: pickCase(raw, "recordId", "RecordId", null as string | null),
+    text: pickCase(raw, "text", "Text", ""),
+  };
+}
+
+function normalizePatchProposal(
+  raw: CoachPatchProposalDtoRaw | null | undefined,
+): CoachPatchProposalDto | null {
+  if (!raw) return null;
+  return {
+    kind: pickCase(raw, "kind", "Kind", ""),
+    description: pickCase(
+      raw,
+      "description",
+      "Description",
+      null as string | null,
+    ),
+    content: pickCase(raw, "content", "Content", null as string | null),
+  };
+}
+
+function normalizeCoachPlan(raw: CoachPlanDtoRaw): CoachPlanDto {
+  const evidenceRaw = pickCase(
+    raw,
+    "evidence",
+    "Evidence",
+    [] as CoachEvidenceDtoRaw[],
+  );
+  const patchRaw = pickCase(
+    raw,
+    "patchProposal",
+    "PatchProposal",
+    null as CoachPatchProposalDtoRaw | null,
+  );
+
+  return {
+    kind: pickCase(raw, "kind", "Kind", ""),
+    title: pickCase(raw, "title", "Title", ""),
+    summary: pickCase(raw, "summary", "Summary", ""),
+    questions: pickCase(raw, "questions", "Questions", [] as string[]),
+    suggestedNextActions: pickCase(
+      raw,
+      "suggestedNextActions",
+      "SuggestedNextActions",
+      [] as string[],
+    ),
+    suggestedTags: pickCase(
+      raw,
+      "suggestedTags",
+      "SuggestedTags",
+      [] as string[],
+    ),
+    evidence: evidenceRaw.map(normalizeEvidence),
+    patchProposal: normalizePatchProposal(patchRaw),
+  };
+}
+
+// ── API functions ───────────────────────────────────────────────
+
+export async function aiHealth(): Promise<AiHealthDto> {
+  const data = await sendCommand<AiHealthDtoRaw>({
+    action: "ai.health",
+    payload: {},
+  });
+  return normalizeHealth(data);
+}
+
+export async function aiChat(prompt: string): Promise<string> {
+  return sendCommand<string>({
+    action: "ai.chat",
+    payload: { prompt },
+  });
+}
+
+export async function aiSummarizeEntry(
+  content: string,
+  fileStem?: string,
+): Promise<string> {
+  return sendCommand<string>({
+    action: "ai.summarize_entry",
+    payload: { content, fileStem },
+  });
+}
+
+export async function coachDaily(
+  payload: CoachSessionPayload = {},
+): Promise<CoachPlanDto> {
+  const data = await sendCommand<CoachPlanDtoRaw>({
+    action: "ai.coach.daily",
+    payload,
+  });
+  return normalizeCoachPlan(data);
+}
+
+export async function coachEvening(
+  payload: CoachSessionPayload = {},
+): Promise<CoachPlanDto> {
+  const data = await sendCommand<CoachPlanDtoRaw>({
+    action: "ai.coach.evening",
+    payload,
+  });
+  return normalizeCoachPlan(data);
+}
+
+export async function coachWeekly(
+  payload: CoachSessionPayload = {},
+): Promise<CoachPlanDto> {
+  const data = await sendCommand<CoachPlanDtoRaw>({
+    action: "ai.coach.weekly",
+    payload,
+  });
+  return normalizeCoachPlan(data);
+}
diff --git a/Journal.App/src/lib/backend/conversations.ts b/Journal.App/src/lib/backend/conversations.ts
new file mode 100644
index 0000000..675ff28
--- /dev/null
+++ b/Journal.App/src/lib/backend/conversations.ts
@@ -0,0 +1,166 @@
+import { sendCommand } from "./client";
+import { pickCase } from "./normalize";
+
+// ── Public types ────────────────────────────────────────────────
+
+export type ConversationDto = {
+  id: string;
+  title: string;
+  createdAt: string;
+  updatedAt: string;
+};
+
+export type ConversationMessageDto = {
+  id: string;
+  role: string;
+  text: string;
+  createdAt: string;
+};
+
+export type ConversationDetailDto = {
+  id: string;
+  title: string;
+  messages: ConversationMessageDto[];
+  createdAt: string;
+  updatedAt: string;
+};
+
+export type ConversationChatResult = {
+  userMessage: ConversationMessageDto;
+  assistantMessage: ConversationMessageDto;
+};
+
+// ── Raw (PascalCase) variants ───────────────────────────────────
+
+type ConversationDtoRaw = {
+  id?: string;
+  title?: string;
+  createdAt?: string;
+  updatedAt?: string;
+  Id?: string;
+  Title?: string;
+  CreatedAt?: string;
+  UpdatedAt?: string;
+};
+
+type ConversationMessageDtoRaw = {
+  id?: string;
+  role?: string;
+  text?: string;
+  createdAt?: string;
+  Id?: string;
+  Role?: string;
+  Text?: string;
+  CreatedAt?: string;
+};
+
+type ConversationDetailDtoRaw = {
+  id?: string;
+  title?: string;
+  messages?: ConversationMessageDtoRaw[];
+  createdAt?: string;
+  updatedAt?: string;
+  Id?: string;
+  Title?: string;
+  Messages?: ConversationMessageDtoRaw[];
+  CreatedAt?: string;
+  UpdatedAt?: string;
+};
+
+type ConversationChatResultRaw = {
+  userMessage?: ConversationMessageDtoRaw;
+  assistantMessage?: ConversationMessageDtoRaw;
+  UserMessage?: ConversationMessageDtoRaw;
+  AssistantMessage?: ConversationMessageDtoRaw;
+};
+
+// ── Normalizers ─────────────────────────────────────────────────
+
+function normalizeMessage(raw: ConversationMessageDtoRaw): ConversationMessageDto {
+  return {
+    id: pickCase(raw, "id", "Id", ""),
+    role: pickCase(raw, "role", "Role", ""),
+    text: pickCase(raw, "text", "Text", ""),
+    createdAt: pickCase(raw, "createdAt", "CreatedAt", ""),
+  };
+}
+
+function normalizeConversation(raw: ConversationDtoRaw): ConversationDto {
+  return {
+    id: pickCase(raw, "id", "Id", ""),
+    title: pickCase(raw, "title", "Title", ""),
+    createdAt: pickCase(raw, "createdAt", "CreatedAt", ""),
+    updatedAt: pickCase(raw, "updatedAt", "UpdatedAt", ""),
+  };
+}
+
+function normalizeDetail(raw: ConversationDetailDtoRaw): ConversationDetailDto {
+  const msgs = pickCase(raw, "messages", "Messages", [] as ConversationMessageDtoRaw[]);
+  return {
+    id: pickCase(raw, "id", "Id", ""),
+    title: pickCase(raw, "title", "Title", ""),
+    messages: msgs.map(normalizeMessage),
+    createdAt: pickCase(raw, "createdAt", "CreatedAt", ""),
+    updatedAt: pickCase(raw, "updatedAt", "UpdatedAt", ""),
+  };
+}
+
+function normalizeChatResult(raw: ConversationChatResultRaw): ConversationChatResult {
+  const userRaw = pickCase(raw, "userMessage", "UserMessage", {} as ConversationMessageDtoRaw);
+  const assistantRaw = pickCase(raw, "assistantMessage", "AssistantMessage", {} as ConversationMessageDtoRaw);
+  return {
+    userMessage: normalizeMessage(userRaw),
+    assistantMessage: normalizeMessage(assistantRaw),
+  };
+}
+
+// ── API functions ───────────────────────────────────────────────
+
+export async function listConversations(): Promise<ConversationDto[]> {
+  const data = await sendCommand<ConversationDtoRaw[]>({
+    action: "conversations.list",
+    payload: {},
+  });
+  return (data ?? []).map(normalizeConversation);
+}
+
+export async function getConversation(id: string): Promise<ConversationDetailDto> {
+  const data = await sendCommand<ConversationDetailDtoRaw>({
+    action: "conversations.get",
+    id,
+    payload: {},
+  });
+  return normalizeDetail(data);
+}
+
+export async function createConversation(title: string): Promise<ConversationDto> {
+  const data = await sendCommand<ConversationDtoRaw>({
+    action: "conversations.create",
+    payload: { title },
+  });
+  return normalizeConversation(data);
+}
+
+export async function updateConversation(id: string, title: string): Promise<boolean> {
+  return sendCommand<boolean>({
+    action: "conversations.update",
+    id,
+    payload: { title },
+  });
+}
+
+export async function deleteConversation(id: string): Promise<boolean> {
+  return sendCommand<boolean>({
+    action: "conversations.delete",
+    id,
+    payload: {},
+  });
+}
+
+export async function conversationChat(conversationId: string, prompt: string): Promise<ConversationChatResult> {
+  const data = await sendCommand<ConversationChatResultRaw>({
+    action: "conversations.chat",
+    payload: { conversationId, prompt },
+  });
+  return normalizeChatResult(data);
+}
diff --git a/Journal.App/src/lib/components/CoachPanel.svelte b/Journal.App/src/lib/components/CoachPanel.svelte
new file mode 100644
index 0000000..135ff43
--- /dev/null
+++ b/Journal.App/src/lib/components/CoachPanel.svelte
@@ -0,0 +1,691 @@
+<!-- @format -->
+<script lang="ts">
+  import type { AiHealthDto, CoachPlanDto } from "$lib/backend/ai";
+  import {
+    activeConversationStore,
+    sendConversationMessage,
+    clearActiveConversation,
+  } from "$lib/stores/conversations";
+
+  export let health: AiHealthDto | null = null;
+  export let healthChecking = false;
+
+  export let coachBusy = false;
+  export let coachError = "";
+  export let coachPlan: CoachPlanDto | null = null;
+  export let coachKind = "";
+
+  $: chatBusy = $activeConversationStore.busy;
+  $: chatMessages = $activeConversationStore.messages;
+
+  let chatInput = "";
+
+  function handleChatSubmit() {
+    const prompt = chatInput.trim();
+    if (!prompt) return;
+    chatInput = "";
+    void sendConversationMessage(prompt);
+  }
+
+  function handleChatKeydown(event: KeyboardEvent) {
+    if (event.key === "Enter" && !event.shiftKey) {
+      event.preventDefault();
+      handleChatSubmit();
+    }
+  }
+
+  const kindLabels: Record<string, string> = {
+    daily: "Daily Check-In",
+    daily_checkin: "Daily Check-In",
+    evening: "Evening Review",
+    evening_review: "Evening Review",
+    weekly: "Weekly Review",
+    weekly_review: "Weekly Review",
+  };
+</script>
+
+<div class="coach-panel">
+  <!-- Health banner -->
+  <div
+    class="health-banner"
+    class:is-healthy={health?.healthy}
+    class:is-unhealthy={health && !health.healthy}
+  >
+    {#if healthChecking}
+      <span class="health-dot checking"></span>
+      <span class="health-label">Checking AI status…</span>
+    {:else if health}
+      <span
+        class="health-dot"
+        class:healthy={health.healthy}
+        class:unhealthy={!health.healthy}
+      ></span>
+      <span class="health-label">
+        {health.provider || "AI"} — {health.healthy ? "Ready" : "Unavailable"}
+      </span>
+      {#if health.message}
+        <span class="health-message">{health.message}</span>
+      {/if}
+    {:else}
+      <span class="health-dot unknown"></span>
+      <span class="health-label">AI status unknown</span>
+    {/if}
+  </div>
+
+  <!-- Coach result -->
+  {#if coachBusy}
+    <div class="coach-loading">
+      <div class="spinner"></div>
+      <p>Running {kindLabels[coachKind] ?? "coach session"}…</p>
+      <p class="loading-hint">
+        This may take a moment while the model generates a response.
+      </p>
+    </div>
+  {:else if coachError}
+    <div class="coach-error">
+      <span class="material-symbols-outlined error-icon">error</span>
+      <p>{coachError}</p>
+    </div>
+  {:else if coachPlan}
+    <article class="coach-plan">
+      <header class="plan-header">
+        <span class="plan-kind"
+          >{kindLabels[coachPlan.kind] ?? coachPlan.kind}</span
+        >
+        <h2>{coachPlan.title}</h2>
+      </header>
+
+      {#if coachPlan.summary}
+        <section class="plan-section">
+          <h3>Summary</h3>
+          <p>{coachPlan.summary}</p>
+        </section>
+      {/if}
+
+      {#if coachPlan.questions.length > 0}
+        <section class="plan-section">
+          <h3>Reflection Questions</h3>
+          <ol class="plan-list">
+            {#each coachPlan.questions as question}
+              <li>{question}</li>
+            {/each}
+          </ol>
+        </section>
+      {/if}
+
+      {#if coachPlan.suggestedNextActions.length > 0}
+        <section class="plan-section">
+          <h3>Suggested Next Actions</h3>
+          <ul class="plan-list">
+            {#each coachPlan.suggestedNextActions as action}
+              <li>{action}</li>
+            {/each}
+          </ul>
+        </section>
+      {/if}
+
+      {#if coachPlan.suggestedTags.length > 0}
+        <section class="plan-section">
+          <h3>Suggested Tags</h3>
+          <div class="tag-list">
+            {#each coachPlan.suggestedTags as tag}
+              <span class="tag">{tag}</span>
+            {/each}
+          </div>
+        </section>
+      {/if}
+
+      {#if coachPlan.evidence.length > 0}
+        <section class="plan-section">
+          <h3>Evidence</h3>
+          <ul class="evidence-list">
+            {#each coachPlan.evidence as item}
+              <li>
+                <span class="evidence-text">{item.text}</span>
+                {#if item.recordId}
+                  <span class="evidence-ref">({item.recordId})</span>
+                {/if}
+              </li>
+            {/each}
+          </ul>
+        </section>
+      {/if}
+
+      {#if coachPlan.patchProposal}
+        <section class="plan-section">
+          <h3>Patch Proposal</h3>
+          <div class="patch-proposal">
+            <span class="patch-kind">{coachPlan.patchProposal.kind}</span>
+            {#if coachPlan.patchProposal.description}
+              <p>{coachPlan.patchProposal.description}</p>
+            {/if}
+            {#if coachPlan.patchProposal.content}
+              <pre class="patch-content">{coachPlan.patchProposal.content}</pre>
+            {/if}
+          </div>
+        </section>
+      {/if}
+    </article>
+  {:else if chatMessages.length === 0 && !chatBusy}
+    <div class="coach-empty">
+      <span class="material-symbols-outlined empty-icon">psychology</span>
+      <p>
+        Select a coaching session from the sidebar, or ask a question using
+        the input below.
+      </p>
+    </div>
+  {/if}
+
+  <!-- Chat conversation -->
+  {#if chatMessages.length > 0}
+    <section class="chat-history">
+      <h3>Conversation</h3>
+      <div class="chat-messages">
+        {#each chatMessages as msg}
+          <div class="chat-msg" class:chat-user={msg.role === "user"} class:chat-assistant={msg.role === "assistant"} class:chat-error={msg.role === "error"}>
+            <span class="chat-role">{msg.role === "user" ? "You" : msg.role === "error" ? "Error" : "AI"}</span>
+            <div class="chat-text">{msg.text}</div>
+          </div>
+        {/each}
+        {#if chatBusy}
+          <div class="chat-msg chat-assistant">
+            <span class="chat-role">AI</span>
+            <div class="chat-thinking">
+              <div class="spinner-sm"></div>
+              <span>Thinking…</span>
+            </div>
+          </div>
+        {/if}
+      </div>
+    </section>
+  {:else if chatBusy}
+    <div class="chat-loading">
+      <div class="spinner"></div>
+      <p>Thinking…</p>
+    </div>
+  {/if}
+
+  <!-- Chat input (pinned at bottom) -->
+  <div class="chat-input-bar">
+    <div class="chat-input-row">
+      <input
+        type="text"
+        bind:value={chatInput}
+        placeholder="Ask a question…"
+        on:keydown={handleChatKeydown}
+        disabled={chatBusy}
+      />
+      <button
+        type="button"
+        class="chat-send-btn"
+        on:click={handleChatSubmit}
+        disabled={chatBusy || !chatInput.trim()}
+        aria-label="Send"
+      >
+        <span class="material-symbols-outlined">send</span>
+      </button>
+    </div>
+    {#if chatMessages.length > 0}
+      <button type="button" class="chat-clear-btn" on:click={clearActiveConversation}>
+        Clear Chat
+      </button>
+    {/if}
+  </div>
+</div>
+
+<style>
+  .coach-panel {
+    display: flex;
+    flex-direction: column;
+    gap: 20px;
+    padding: 24px 24px 0;
+    overflow: auto;
+    min-height: 0;
+    flex: 1;
+  }
+
+  /* ── Health banner ───────────────────────────────── */
+
+  .health-banner {
+    display: flex;
+    align-items: center;
+    gap: 8px;
+    padding: 10px 14px;
+    border-radius: 10px;
+    border: 1px solid var(--border-soft);
+    background: var(--surface-1);
+    font-size: 0.82rem;
+  }
+
+  .health-dot {
+    width: 8px;
+    height: 8px;
+    border-radius: 50%;
+    flex-shrink: 0;
+
+    &.healthy {
+      background: #4ade80;
+    }
+
+    &.unhealthy {
+      background: #e06c75;
+    }
+
+    &.checking {
+      background: var(--text-dim);
+      animation: pulse 1s ease-in-out infinite;
+    }
+
+    &.unknown {
+      background: var(--text-dim);
+    }
+  }
+
+  .health-label {
+    color: var(--text-primary);
+    font-weight: 500;
+  }
+
+  .health-message {
+    color: var(--text-dim);
+    margin-left: auto;
+  }
+
+  /* ── Coach plan ──────────────────────────────────── */
+
+  .coach-plan {
+    display: flex;
+    flex-direction: column;
+    gap: 18px;
+  }
+
+  .plan-header {
+    display: flex;
+    flex-direction: column;
+    gap: 4px;
+
+    h2 {
+      font-size: 1.15rem;
+      font-weight: 600;
+      color: var(--text-primary);
+    }
+  }
+
+  .plan-kind {
+    font-size: 0.72rem;
+    font-weight: 600;
+    text-transform: uppercase;
+    letter-spacing: 0.06em;
+    color: var(--text-dim);
+  }
+
+  .plan-section {
+    display: flex;
+    flex-direction: column;
+    gap: 8px;
+
+    h3 {
+      font-size: 0.82rem;
+      font-weight: 600;
+      color: var(--text-muted);
+      letter-spacing: 0.01em;
+    }
+
+    p {
+      font-size: 0.88rem;
+      color: var(--text-primary);
+      line-height: 1.55;
+    }
+  }
+
+  .plan-list {
+    display: flex;
+    flex-direction: column;
+    gap: 6px;
+    padding-left: 20px;
+
+    li {
+      font-size: 0.86rem;
+      color: var(--text-primary);
+      line-height: 1.5;
+    }
+  }
+
+  .tag-list {
+    display: flex;
+    flex-wrap: wrap;
+    gap: 6px;
+  }
+
+  .tag {
+    padding: 3px 10px;
+    border-radius: 20px;
+    border: 1px solid var(--border-soft);
+    background: var(--surface-2);
+    font-size: 0.76rem;
+    color: var(--text-muted);
+  }
+
+  .evidence-list {
+    display: flex;
+    flex-direction: column;
+    gap: 6px;
+    list-style: none;
+
+    li {
+      padding: 8px 12px;
+      border-radius: 8px;
+      border: 1px solid var(--border-soft);
+      background: var(--surface-1);
+      font-size: 0.84rem;
+      line-height: 1.45;
+    }
+  }
+
+  .evidence-text {
+    color: var(--text-primary);
+  }
+
+  .evidence-ref {
+    color: var(--text-dim);
+    font-size: 0.76rem;
+    margin-left: 6px;
+  }
+
+  .patch-proposal {
+    padding: 12px;
+    border-radius: 8px;
+    border: 1px solid var(--border-soft);
+    background: var(--surface-1);
+    display: flex;
+    flex-direction: column;
+    gap: 8px;
+
+    p {
+      font-size: 0.84rem;
+      color: var(--text-primary);
+      line-height: 1.5;
+    }
+  }
+
+  .patch-kind {
+    font-size: 0.72rem;
+    font-weight: 600;
+    text-transform: uppercase;
+    letter-spacing: 0.04em;
+    color: var(--text-dim);
+  }
+
+  .patch-content {
+    font-family: "Cascadia Code", "Fira Code", monospace;
+    font-size: 0.8rem;
+    color: var(--text-muted);
+    background: var(--surface-2);
+    padding: 10px 12px;
+    border-radius: 6px;
+    border: 1px solid var(--border-soft);
+    overflow-x: auto;
+    white-space: pre-wrap;
+    word-break: break-word;
+  }
+
+  /* ── Chat conversation ────────────────────────────── */
+
+  .chat-history {
+    display: flex;
+    flex-direction: column;
+    gap: 10px;
+    border-top: 1px solid var(--border-soft);
+    padding-top: 18px;
+
+    h3 {
+      font-size: 0.82rem;
+      font-weight: 600;
+      color: var(--text-muted);
+    }
+  }
+
+  .chat-messages {
+    display: flex;
+    flex-direction: column;
+    gap: 8px;
+  }
+
+  .chat-msg {
+    display: flex;
+    flex-direction: column;
+    gap: 4px;
+    padding: 10px 14px;
+    border-radius: 10px;
+    border: 1px solid var(--border-soft);
+  }
+
+  .chat-user {
+    background: var(--surface-2);
+    align-self: flex-end;
+    max-width: 85%;
+  }
+
+  .chat-assistant {
+    background: var(--surface-1);
+    align-self: flex-start;
+    max-width: 85%;
+  }
+
+  .chat-error {
+    background: rgba(224, 108, 117, 0.08);
+    border-color: #e06c75;
+    align-self: flex-start;
+    max-width: 85%;
+  }
+
+  .chat-role {
+    font-size: 0.7rem;
+    font-weight: 600;
+    text-transform: uppercase;
+    letter-spacing: 0.04em;
+    color: var(--text-dim);
+  }
+
+  .chat-error .chat-role {
+    color: #e06c75;
+  }
+
+  .chat-text {
+    font-size: 0.86rem;
+    color: var(--text-primary);
+    line-height: 1.55;
+    white-space: pre-wrap;
+    word-break: break-word;
+  }
+
+  .chat-thinking {
+    display: flex;
+    align-items: center;
+    gap: 8px;
+    font-size: 0.82rem;
+    color: var(--text-dim);
+  }
+
+  .spinner-sm {
+    width: 16px;
+    height: 16px;
+    border: 2px solid var(--border-soft);
+    border-top-color: var(--text-muted);
+    border-radius: 50%;
+    animation: spin 0.7s linear infinite;
+  }
+
+  /* ── Empty / loading / error ─────────────────────── */
+
+  .coach-empty {
+    display: flex;
+    flex-direction: column;
+    align-items: center;
+    justify-content: center;
+    gap: 10px;
+    padding: 60px 20px;
+    text-align: center;
+
+    .empty-icon {
+      font-size: 2.8rem;
+      color: var(--text-dim);
+    }
+
+    p {
+      font-size: 0.88rem;
+      color: var(--text-dim);
+      max-width: 320px;
+    }
+  }
+
+  .coach-loading,
+  .chat-loading {
+    display: flex;
+    flex-direction: column;
+    align-items: center;
+    gap: 12px;
+    padding: 40px 20px;
+    text-align: center;
+
+    p {
+      font-size: 0.88rem;
+      color: var(--text-muted);
+    }
+  }
+
+  .loading-hint {
+    font-size: 0.78rem !important;
+    color: var(--text-dim) !important;
+  }
+
+  .coach-error {
+    display: flex;
+    align-items: flex-start;
+    gap: 8px;
+    padding: 12px 14px;
+    border-radius: 10px;
+    border: 1px solid #e06c75;
+    background: rgba(224, 108, 117, 0.08);
+
+    .error-icon {
+      color: #e06c75;
+      font-size: 1.1rem;
+      flex-shrink: 0;
+      margin-top: 1px;
+    }
+
+    p {
+      font-size: 0.84rem;
+      color: var(--text-primary);
+      line-height: 1.45;
+    }
+  }
+
+  .spinner {
+    width: 28px;
+    height: 28px;
+    border: 3px solid var(--border-soft);
+    border-top-color: var(--text-muted);
+    border-radius: 50%;
+    animation: spin 0.7s linear infinite;
+  }
+
+  @keyframes spin {
+    to {
+      transform: rotate(360deg);
+    }
+  }
+
+  @keyframes pulse {
+    0%,
+    100% {
+      opacity: 0.4;
+    }
+    50% {
+      opacity: 1;
+    }
+  }
+
+  /* ── Chat input bar (pinned bottom) ─────────────── */
+
+  .chat-input-bar {
+    position: sticky;
+    bottom: 0;
+    display: flex;
+    flex-direction: column;
+    gap: 6px;
+    padding: 12px 0 24px;
+    background: var(--bg-editor);
+    margin-top: auto;
+  }
+
+  .chat-input-row {
+    display: flex;
+    align-items: center;
+    gap: 6px;
+    border: 1px solid var(--border-soft);
+    border-radius: 10px;
+    background: var(--surface-1);
+    padding: 6px 8px 6px 14px;
+
+    input {
+      flex: 1;
+      min-width: 0;
+      font-size: 0.86rem;
+      color: var(--text-primary);
+
+      &::placeholder {
+        color: var(--text-dim);
+      }
+
+      &:disabled {
+        opacity: 0.5;
+      }
+    }
+  }
+
+  .chat-send-btn {
+    width: 32px;
+    height: 32px;
+    display: grid;
+    place-items: center;
+    border-radius: 8px;
+    color: var(--text-muted);
+    cursor: pointer;
+    border: 1px solid transparent;
+    flex-shrink: 0;
+
+    .material-symbols-outlined {
+      font-size: 1rem;
+    }
+
+    &:hover {
+      background: var(--bg-hover);
+      border-color: var(--border-soft);
+      color: var(--text-primary);
+    }
+
+    &:disabled {
+      opacity: 0.4;
+      cursor: default;
+    }
+  }
+
+  .chat-clear-btn {
+    align-self: flex-start;
+    padding: 4px 10px;
+    border-radius: 6px;
+    border: 1px solid var(--border-soft);
+    background: transparent;
+    color: var(--text-dim);
+    font-size: 0.74rem;
+    cursor: pointer;
+
+    &:hover {
+      color: var(--text-primary);
+      border-color: var(--border-strong);
+      background: var(--bg-hover);
+    }
+  }
+</style>
diff --git a/Journal.App/src/lib/components/EditorPanel.svelte b/Journal.App/src/lib/components/EditorPanel.svelte
index e890f27..7f714b8 100644
--- a/Journal.App/src/lib/components/EditorPanel.svelte
+++ b/Journal.App/src/lib/components/EditorPanel.svelte
@@ -4,6 +4,8 @@
   import ListEditor from "$lib/components/editor/ListEditor.svelte";
   import TodoEditor from "$lib/components/editor/TodoEditor.svelte";
   import MarkdownEditor from "$lib/components/editor/MarkdownEditor.svelte";
+  import CoachPanel from "$lib/components/CoachPanel.svelte";
+  import { aiStatusStore, coachStateStore } from "$lib/stores/ai";
 
   export let activeSection = "entries";
   export let openDocumentId = "entries/daily-notes";
@@ -154,6 +156,15 @@
         </ul>
       {/if}
     </section>
+  {:else if activeSection === "coach"}
+    <CoachPanel
+      health={$aiStatusStore.health}
+      healthChecking={$aiStatusStore.checking}
+      coachBusy={$coachStateStore.busy}
+      coachError={$coachStateStore.error}
+      coachPlan={$coachStateStore.plan}
+      coachKind={$coachStateStore.kind}
+    />
   {:else if !openDocumentId}
     <div class="editor-empty">
       <span class="material-symbols-outlined empty-icon">edit_note</span>
diff --git a/Journal.App/src/lib/components/Navbar.svelte b/Journal.App/src/lib/components/Navbar.svelte
index 1141680..f33b41d 100644
--- a/Journal.App/src/lib/components/Navbar.svelte
+++ b/Journal.App/src/lib/components/Navbar.svelte
@@ -15,6 +15,7 @@
     { id: "fragments", label: "Fragments", icon: "auto_stories" },
     { id: "todos", label: "To-Do List", icon: "checklist" },
     { id: "lists", label: "Lists", icon: "lists" },
+    { id: "coach", label: "Coach", icon: "psychology" },
   ];
 
   function selectItem(id: string) {
diff --git a/Journal.App/src/lib/components/SidePanel.svelte b/Journal.App/src/lib/components/SidePanel.svelte
index 3b9d0c4..79fcc15 100644
--- a/Journal.App/src/lib/components/SidePanel.svelte
+++ b/Journal.App/src/lib/components/SidePanel.svelte
@@ -32,6 +32,24 @@
   } from "$lib/stores/todos";
   import { vaultUnlocked } from "$lib/stores/session";
   import { extractEntryTags } from "$lib/utils/metadata";
+  import {
+    aiStatusStore,
+    coachStateStore,
+    checkAiHealth,
+    runCoachSession,
+    clearCoachPlan,
+  } from "$lib/stores/ai";
+  import type { CoachSessionPayload } from "$lib/backend/ai";
+  import {
+    conversationsStore,
+    activeConversationStore,
+    loadConversations,
+    createNewConversation,
+    openConversation,
+    renameConversation,
+    removeConversation,
+    clearActiveConversation,
+  } from "$lib/stores/conversations";
 
   export let activeSection = "entries";
   export let activeDocumentId = "";
@@ -94,8 +112,90 @@
     fragments: "Fragments",
     todos: "To-Do List",
     lists: "Lists",
+    coach: "Coach",
   };
 
+  // ── Coach state ──────────────────────────────────
+  let coachHealthChecked = false;
+  let conversationsLoaded = false;
+  let editingConversationId = "";
+  let editingConversationTitle = "";
+
+  const MAX_CONTEXT_ENTRIES = 5;
+  const MAX_CONTEXT_FRAGMENTS = 10;
+
+  function gatherCoachContext(): CoachSessionPayload {
+    const now = new Date();
+    const dateLocal = `${now.getFullYear()}-${String(now.getMonth() + 1).padStart(2, "0")}-${String(now.getDate()).padStart(2, "0")}`;
+    const recentEntries = $entriesStore
+      .filter((e) => e.initialContent?.trim())
+      .slice(0, MAX_CONTEXT_ENTRIES)
+      .map((e) => e.initialContent);
+    const recentFragments = $fragmentsStore
+      .filter((f) => f.initialContent?.trim())
+      .slice(0, MAX_CONTEXT_FRAGMENTS)
+      .map((f) => f.initialContent);
+    return { dateLocal, recentEntries, recentFragments };
+  }
+
+  function handleCoachSession(kind: string) {
+    const payload = gatherCoachContext();
+    if (kind === "weekly") {
+      const now = new Date();
+      const weekDay = (now.getDay() + 6) % 7;
+      const start = new Date(now);
+      start.setDate(now.getDate() - weekDay);
+      const end = new Date(start);
+      end.setDate(start.getDate() + 6);
+      payload.weekStartLocal = `${start.getFullYear()}-${String(start.getMonth() + 1).padStart(2, "0")}-${String(start.getDate()).padStart(2, "0")}`;
+      payload.weekEndLocal = `${end.getFullYear()}-${String(end.getMonth() + 1).padStart(2, "0")}-${String(end.getDate()).padStart(2, "0")}`;
+    }
+    void runCoachSession(kind, payload);
+  }
+
+  // ── Conversation helpers ──────────────────────────
+  function ensureConversationsLoaded() {
+    if (!conversationsLoaded) {
+      conversationsLoaded = true;
+      void loadConversations();
+    }
+  }
+
+  $: if (activeSection === "coach") {
+    ensureConversationsLoaded();
+  }
+
+  function formatConversationDefaultTitle(): string {
+    const now = new Date();
+    return now.toLocaleString(undefined, {
+      month: "short",
+      day: "numeric",
+      year: "numeric",
+      hour: "numeric",
+      minute: "2-digit",
+    });
+  }
+
+  function startRenamingConversation(id: string, currentTitle: string) {
+    editingConversationId = id;
+    editingConversationTitle = currentTitle;
+  }
+
+  function commitRename() {
+    const trimmed = editingConversationTitle.trim();
+    if (trimmed && editingConversationId) {
+      void renameConversation(editingConversationId, trimmed);
+    }
+    editingConversationId = "";
+    editingConversationTitle = "";
+  }
+
+  function cancelRename() {
+    editingConversationId = "";
+    editingConversationTitle = "";
+  }
+
+
   const today = new Date();
   let calendarYear = today.getFullYear();
   let calendarMonth = today.getMonth();
@@ -938,15 +1038,17 @@
           <span class="material-symbols-outlined">calendar_month</span>
         </button>
       {/if}
-      <button
-        type="button"
-        class="panel-action"
-        aria-label="Add item"
-        title="Add item"
-        on:click={handleAddItem}
-      >
-        <span class="material-symbols-outlined">add</span>
-      </button>
+      {#if activeSection !== "coach"}
+        <button
+          type="button"
+          class="panel-action"
+          aria-label="Add item"
+          title="Add item"
+          on:click={handleAddItem}
+        >
+          <span class="material-symbols-outlined">add</span>
+        </button>
+      {/if}
     </div>
   </header>
 
@@ -1085,6 +1187,145 @@
         Last refreshed: {calendarLastRefreshedAt || "Not yet"}
       </p>
     </div>
+  {:else if activeSection === "coach"}
+    <div class="coach-sidebar">
+      <div class="coach-health">
+        <button
+          type="button"
+          class="coach-health-btn"
+          on:click={() => void checkAiHealth()}
+          disabled={$aiStatusStore.checking}
+        >
+          <span
+            class="health-indicator"
+            class:healthy={$aiStatusStore.health?.healthy}
+            class:unhealthy={$aiStatusStore.health &&
+              !$aiStatusStore.health.healthy}
+            class:checking={$aiStatusStore.checking}
+          ></span>
+          {$aiStatusStore.checking
+            ? "Checking…"
+            : $aiStatusStore.health
+              ? $aiStatusStore.health.healthy
+                ? "AI Ready"
+                : "AI Unavailable"
+              : "Check AI Status"}
+        </button>
+      </div>
+
+      <div class="panel-subsection">
+        <h3>Coaching Sessions</h3>
+        <div class="coach-session-buttons">
+          <button
+            type="button"
+            class="coach-session-btn"
+            on:click={() => handleCoachSession("daily")}
+            disabled={$coachStateStore.busy}
+          >
+            <span class="material-symbols-outlined">wb_sunny</span>
+            Daily Check-In
+          </button>
+          <button
+            type="button"
+            class="coach-session-btn"
+            on:click={() => handleCoachSession("evening")}
+            disabled={$coachStateStore.busy}
+          >
+            <span class="material-symbols-outlined">dark_mode</span>
+            Evening Review
+          </button>
+          <button
+            type="button"
+            class="coach-session-btn"
+            on:click={() => handleCoachSession("weekly")}
+            disabled={$coachStateStore.busy}
+          >
+            <span class="material-symbols-outlined">date_range</span>
+            Weekly Review
+          </button>
+        </div>
+        {#if $coachStateStore.plan}
+          <button
+            type="button"
+            class="coach-clear-btn"
+            on:click={clearCoachPlan}
+          >
+            Clear Result
+          </button>
+        {/if}
+      </div>
+
+      <div class="panel-subsection">
+        <div class="subsection-header">
+          <h3>Conversations</h3>
+          <button
+            type="button"
+            class="subsection-action"
+            on:click={() => {
+              clearActiveConversation();
+              void createNewConversation(formatConversationDefaultTitle());
+            }}
+            aria-label="New conversation"
+          >
+            <span class="material-symbols-outlined">add</span>
+          </button>
+        </div>
+
+        {#if $conversationsStore.busy}
+          <p class="section-copy">Loading…</p>
+        {:else if $conversationsStore.items.length === 0}
+          <p class="section-copy">No conversations yet.</p>
+        {:else}
+          <ul class="panel-list">
+            {#each $conversationsStore.items as conv}
+              <li class:is-active={conv.id === $activeConversationStore.id}>
+                {#if editingConversationId === conv.id}
+                  <input
+                    type="text"
+                    class="rename-input"
+                    bind:value={editingConversationTitle}
+                    on:keydown={(e) => {
+                      if (e.key === "Enter") commitRename();
+                      if (e.key === "Escape") cancelRename();
+                    }}
+                    on:blur={commitRename}
+                    autofocus
+                  />
+                {:else}
+                  <button
+                    type="button"
+                    class="item-label"
+                    on:click={() => void openConversation(conv.id)}
+                  >
+                    {conv.title}
+                  </button>
+                  <div class="item-actions">
+                    <button
+                      type="button"
+                      class="item-action"
+                      on:click|stopPropagation={() =>
+                        startRenamingConversation(conv.id, conv.title)}
+                      aria-label="Rename conversation"
+                    >
+                      <span class="material-symbols-outlined">edit</span>
+                    </button>
+                    <button
+                      type="button"
+                      class="item-action item-action-danger"
+                      on:click|stopPropagation={() =>
+                        void removeConversation(conv.id)}
+                      aria-label="Delete conversation"
+                    >
+                      <span class="material-symbols-outlined">delete</span>
+                    </button>
+                  </div>
+                {/if}
+              </li>
+            {/each}
+          </ul>
+        {/if}
+      </div>
+    </div>
   {:else}
     <div class="panel-search">
       <span class="material-symbols-outlined">search</span>
@@ -1597,4 +1838,166 @@
       grid-template-columns: 1fr;
     }
   }
+
+  /* ── Coach sidebar ────────────────────────────────── */
+
+  .coach-sidebar {
+    display: flex;
+    flex-direction: column;
+    gap: 16px;
+    overflow: auto;
+    min-height: 0;
+  }
+
+  .coach-health {
+    display: flex;
+  }
+
+  .coach-health-btn {
+    display: flex;
+    align-items: center;
+    gap: 8px;
+    width: 100%;
+    padding: 8px 12px;
+    border-radius: 8px;
+    border: 1px solid var(--border-soft);
+    background: var(--surface-1);
+    color: var(--text-muted);
+    font-size: 0.8rem;
+    cursor: pointer;
+
+    &:hover {
+      background: var(--bg-hover);
+      border-color: var(--border-strong);
+      color: var(--text-primary);
+    }
+
+    &:disabled {
+      opacity: 0.6;
+      cursor: default;
+    }
+  }
+
+  .health-indicator {
+    width: 8px;
+    height: 8px;
+    border-radius: 50%;
+    flex-shrink: 0;
+    background: var(--text-dim);
+
+    &.healthy {
+      background: #4ade80;
+    }
+
+    &.unhealthy {
+      background: #e06c75;
+    }
+
+    &.checking {
+      animation: coach-pulse 1s ease-in-out infinite;
+    }
+  }
+
+  .coach-session-buttons {
+    display: flex;
+    flex-direction: column;
+    gap: 4px;
+  }
+
+  .coach-session-btn {
+    display: flex;
+    align-items: center;
+    gap: 8px;
+    width: 100%;
+    padding: 9px 12px;
+    border-radius: 8px;
+    border: 1px solid var(--border-soft);
+    background: var(--surface-1);
+    color: var(--text-muted);
+    font-size: 0.82rem;
+    cursor: pointer;
+    text-align: left;
+
+    .material-symbols-outlined {
+      font-size: 1rem;
+    }
+
+    &:hover {
+      background: var(--bg-hover);
+      border-color: var(--border-strong);
+      color: var(--text-primary);
+    }
+
+    &:disabled {
+      opacity: 0.5;
+      cursor: default;
+    }
+  }
+
+  .coach-clear-btn {
+    align-self: flex-start;
+    padding: 4px 10px;
+    border-radius: 6px;
+    border: 1px solid var(--border-soft);
+    background: transparent;
+    color: var(--text-dim);
+    font-size: 0.74rem;
+    cursor: pointer;
+
+    &:hover {
+      color: var(--text-primary);
+      border-color: var(--border-strong);
+      background: var(--bg-hover);
+    }
+  }
+
+  .subsection-header {
+    display: flex;
+    align-items: center;
+    justify-content: space-between;
+  }
+
+  .subsection-action {
+    width: 26px;
+    height: 26px;
+    display: grid;
+    place-items: center;
+    border-radius: 6px;
+    border: 1px solid transparent;
+    background: transparent;
+    color: var(--text-dim);
+    cursor: pointer;
+
+    .material-symbols-outlined {
+      font-size: 1rem;
+    }
+
+    &:hover {
+      color: var(--text-primary);
+      border-color: var(--border-soft);
+      background: var(--bg-hover);
+    }
+  }
+
+  .rename-input {
+    width: 100%;
+    font-size: 0.82rem;
+    color: var(--text-primary);
+    background: var(--surface-1);
+    border: 1px solid var(--accent, #6b8afd);
+    border-radius: 6px;
+    padding: 6px 9px;
+    outline: none;
+  }
+
+
+  @keyframes coach-pulse {
+    0%,
+    100% {
+      opacity: 0.4;
+    }
+    50% {
+      opacity: 1;
+    }
+  }
 </style>
diff --git a/Journal.App/src/lib/stores/ai.ts b/Journal.App/src/lib/stores/ai.ts
new file mode 100644
index 0000000..b8f2135
--- /dev/null
+++ b/Journal.App/src/lib/stores/ai.ts
@@ -0,0 +1,140 @@
+import { writable } from "svelte/store";
+import {
+  aiHealth as aiHealthCommand,
+  aiChat as aiChatCommand,
+  coachDaily,
+  coachEvening,
+  coachWeekly,
+  type AiHealthDto,
+  type CoachPlanDto,
+  type CoachSessionPayload,
+} from "$lib/backend/ai";
+
+// ── Store shapes ────────────────────────────────────────────────
+
+type AiStatusState = {
+  checking: boolean;
+  health: AiHealthDto | null;
+};
+
+type CoachState = {
+  busy: boolean;
+  error: string;
+  plan: CoachPlanDto | null;
+  kind: string;
+};
+
+export type ChatMessage = {
+  role: "user" | "assistant" | "error";
+  text: string;
+};
+
+type ChatState = {
+  busy: boolean;
+  messages: ChatMessage[];
+};
+
+// ── Stores ──────────────────────────────────────────────────────
+
+export const aiStatusStore = writable<AiStatusState>({
+  checking: false,
+  health: null,
+});
+
+export const coachStateStore = writable<CoachState>({
+  busy: false,
+  error: "",
+  plan: null,
+  kind: "",
+});
+
+export const chatStateStore = writable<ChatState>({
+  busy: false,
+  messages: [],
+});
+
+// ── Actions ─────────────────────────────────────────────────────
+
+export async function checkAiHealth(): Promise<void> {
+  aiStatusStore.update((s) => ({ ...s, checking: true }));
+  try {
+    const health = await aiHealthCommand();
+    aiStatusStore.set({ checking: false, health });
+  } catch (error) {
+    aiStatusStore.set({
+      checking: false,
+      health: {
+        provider: "",
+        enabled: false,
+        healthy: false,
+        message: error instanceof Error ? error.message : String(error),
+      },
+    });
+  }
+}
+
+const sessionRunners: Record<
+  string,
+  (payload: CoachSessionPayload) => Promise<CoachPlanDto>
+> = {
+  daily: coachDaily,
+  evening: coachEvening,
+  weekly: coachWeekly,
+};
+
+export async function runCoachSession(
+  kind: string,
+  payload: CoachSessionPayload = {},
+): Promise<void> {
+  const runner = sessionRunners[kind];
+  if (!runner) {
+    coachStateStore.set({
+      busy: false,
+      error: `Unknown coach session kind: ${kind}`,
+      plan: null,
+      kind,
+    });
+    return;
+  }
+
+  coachStateStore.set({ busy: true, error: "", plan: null, kind });
+  try {
+    const plan = await runner(payload);
+    coachStateStore.set({ busy: false, error: "", plan, kind });
+  } catch (error) {
+    coachStateStore.set({
+      busy: false,
+      error: error instanceof Error ? error.message : String(error),
+      plan: null,
+      kind,
+    });
+  }
+}
+
+export async function runAiChat(prompt: string): Promise<void> {
+  chatStateStore.update((s) => ({
+    busy: true,
+    messages: [...s.messages, { role: "user", text: prompt }],
+  }));
+  try {
+    const response = await aiChatCommand(prompt);
+    chatStateStore.update((s) => ({
+      busy: false,
+      messages: [...s.messages, { role: "assistant", text: response }],
+    }));
+  } catch (error) {
+    const msg = error instanceof Error ? error.message : String(error);
+    chatStateStore.update((s) => ({
+      busy: false,
+      messages: [...s.messages, { role: "error", text: msg }],
+    }));
+  }
+}
+
+export function clearCoachPlan(): void {
+  coachStateStore.set({ busy: false, error: "", plan: null, kind: "" });
+}
+
+export function clearChat(): void {
+  chatStateStore.set({ busy: false, messages: [] });
+}
diff --git a/Journal.App/src/lib/stores/conversations.ts b/Journal.App/src/lib/stores/conversations.ts
new file mode 100644
index 0000000..33d6377
--- /dev/null
+++ b/Journal.App/src/lib/stores/conversations.ts
@@ -0,0 +1,222 @@
+import { writable, get } from "svelte/store";
+import {
+  listConversations as listConversationsApi,
+  getConversation as getConversationApi,
+  createConversation as createConversationApi,
+  deleteConversation as deleteConversationApi,
+  updateConversation as updateConversationApi,
+  conversationChat as conversationChatApi,
+  type ConversationDto,
+  type ConversationMessageDto,
+} from "$lib/backend/conversations";
+
+// ── Store shapes ────────────────────────────────────────────────
+
+type ConversationsState = {
+  items: ConversationDto[];
+  busy: boolean;
+  error: string;
+};
+
+type ActiveConversationState = {
+  id: string;
+  title: string;
+  messages: ConversationMessageDto[];
+  busy: boolean;
+  error: string;
+};
+
+// ── Stores ──────────────────────────────────────────────────────
+
+export const conversationsStore = writable<ConversationsState>({
+  items: [],
+  busy: false,
+  error: "",
+});
+
+export const activeConversationStore = writable<ActiveConversationState>({
+  id: "",
+  title: "",
+  messages: [],
+  busy: false,
+  error: "",
+});
+
+// ── Actions ─────────────────────────────────────────────────────
+
+export async function loadConversations(): Promise<void> {
+  conversationsStore.update((s) => ({ ...s, busy: true, error: "" }));
+  try {
+    const items = await listConversationsApi();
+    conversationsStore.set({ items, busy: false, error: "" });
+  } catch (error) {
+    conversationsStore.update((s) => ({
+      ...s,
+      busy: false,
+      error: error instanceof Error ? error.message : String(error),
+    }));
+  }
+}
+
+export async function createNewConversation(
+  title: string,
+): Promise<string | null> {
+  try {
+    const conv = await createConversationApi(title);
+    conversationsStore.update((s) => ({
+      ...s,
+      items: [conv, ...s.items],
+    }));
+    // Auto-open the new conversation
+    activeConversationStore.set({
+      id: conv.id,
+      title: conv.title,
+      messages: [],
+      busy: false,
+      error: "",
+    });
+    return conv.id;
+  } catch (error) {
+    conversationsStore.update((s) => ({
+      ...s,
+      error: error instanceof Error ? error.message : String(error),
+    }));
+    return null;
+  }
+}
+
+export async function openConversation(id: string): Promise<void> {
+  activeConversationStore.update((s) => ({
+    ...s,
+    id,
+    busy: true,
+    error: "",
+  }));
+  try {
+    const detail = await getConversationApi(id);
+    activeConversationStore.set({
+      id: detail.id,
+      title: detail.title,
+      messages: detail.messages,
+      busy: false,
+      error: "",
+    });
+  } catch (error) {
+    activeConversationStore.update((s) => ({
+      ...s,
+      busy: false,
+      error: error instanceof Error ? error.message : String(error),
+    }));
+  }
+}
+
+export async function sendConversationMessage(
+  prompt: string,
+): Promise<void> {
+  const state = get(activeConversationStore);
+  if (!state.id) {
+    // Auto-create a conversation from the first message
+    const title =
+      prompt.length > 40 ? prompt.slice(0, 37) + "..." : prompt;
+    const convId = await createNewConversation(title);
+    if (!convId) return;
+  }
+
+  const currentId = get(activeConversationStore).id;
+  if (!currentId) return;
+
+  // Optimistically add user message
+  const tempUserMsg: ConversationMessageDto = {
+    id: `temp-${Date.now()}`,
+    role: "user",
+    text: prompt,
+    createdAt: new Date().toISOString(),
+  };
+
+  activeConversationStore.update((s) => ({
+    ...s,
+    messages: [...s.messages, tempUserMsg],
+    busy: true,
+    error: "",
+  }));
+
+  try {
+    const result = await conversationChatApi(currentId, prompt);
+    activeConversationStore.update((s) => ({
+      ...s,
+      busy: false,
+      // Replace temp user message + add assistant message
+      messages: [
+        ...s.messages.filter((m) => m.id !== tempUserMsg.id),
+        result.userMessage,
+        result.assistantMessage,
+      ],
+    }));
+    // Update conversation list (updated_at changes)
+    void loadConversations();
+  } catch (error) {
+    const errorMsg: ConversationMessageDto = {
+      id: `error-${Date.now()}`,
+      role: "error",
+      text: error instanceof Error ? error.message : String(error),
+      createdAt: new Date().toISOString(),
+    };
+    activeConversationStore.update((s) => ({
+      ...s,
+      busy: false,
+      messages: [...s.messages, errorMsg],
+    }));
+  }
+}
+
+export async function renameConversation(
+  id: string,
+  title: string,
+): Promise<void> {
+  try {
+    await updateConversationApi(id, title);
+    conversationsStore.update((s) => ({
+      ...s,
+      items: s.items.map((c) => (c.id === id ? { ...c, title } : c)),
+    }));
+    const active = get(activeConversationStore);
+    if (active.id === id) {
+      activeConversationStore.update((s) => ({ ...s, title }));
+    }
+  } catch (error) {
+    conversationsStore.update((s) => ({
+      ...s,
+      error: error instanceof Error ? error.message : String(error),
+    }));
+  }
+}
+
+export async function removeConversation(id: string): Promise<void> {
+  try {
+    await deleteConversationApi(id);
+    conversationsStore.update((s) => ({
+      ...s,
+      items: s.items.filter((c) => c.id !== id),
+    }));
+    // If this was the active conversation, clear it
+    const active = get(activeConversationStore);
+    if (active.id === id) {
+      clearActiveConversation();
+    }
+  } catch (error) {
+    conversationsStore.update((s) => ({
+      ...s,
+      error: error instanceof Error ? error.message : String(error),
+    }));
+  }
+}
+
+export function clearActiveConversation(): void {
+  activeConversationStore.set({
+    id: "",
+    title: "",
+    messages: [],
+    busy: false,
+    error: "",
+  });
+}
diff --git a/Journal.App/src/lib/stores/settings.ts b/Journal.App/src/lib/stores/settings.ts
index bf4174c..a96b9c7 100644
--- a/Journal.App/src/lib/stores/settings.ts
+++ b/Journal.App/src/lib/stores/settings.ts
@@ -10,6 +10,7 @@ const startupViews = [
   "fragments",
   "todos",
   "lists",
+  "coach",
 ] as const;
 const defaultStartupView = "entries";
 export type StartupView = (typeof startupViews)[number];
diff --git a/Journal.App/src/routes/+page.svelte b/Journal.App/src/routes/+page.svelte
index ee1470a..1b45696 100644
--- a/Journal.App/src/routes/+page.svelte
+++ b/Journal.App/src/routes/+page.svelte
@@ -109,8 +109,8 @@
       case "calendar":
       case "fragments":
       case "todos":
-      case "lists":
       case "entries":
+      case "coach":
         return value;
       default:
         return "entries";
@@ -126,6 +126,7 @@
       case "fragments":
       case "todos":
       case "lists":
+      case "coach":
         return normalized;
       default:
         return null;
diff --git a/Journal.Core/Dtos/CoachDtos.cs b/Journal.Core/Dtos/CoachDtos.cs
new file mode 100644
index 0000000..7fd4235
--- /dev/null
+++ b/Journal.Core/Dtos/CoachDtos.cs
@@ -0,0 +1,32 @@
+namespace Journal.Core.Dtos;
+
+public sealed record CoachPlanDto(
+    string Kind,
+    string Title,
+    string Summary,
+    IReadOnlyList<string> Questions,
+    IReadOnlyList<string> SuggestedNextActions,
+    IReadOnlyList<string> SuggestedTags,
+    IReadOnlyList<CoachEvidenceDto> Evidence,
+    CoachPatchProposalDto? PatchProposal = null);
+
+public sealed record CoachEvidenceDto(
+    string? RecordId,
+    string Text);
+
+public sealed record CoachPatchProposalDto(
+    string Kind,
+    string? Description = null,
+    string? Content = null);
+
+public sealed record CoachContextDto(
+    string DateLocal,
+    string? WeekStartLocal = null,
+    string? WeekEndLocal = null,
+    IReadOnlyList<string>? RecentEntries = null,
+    IReadOnlyList<string>? RecentFragments = null,
+    CoachPreferencesDto? Preferences = null);
+
+public sealed record CoachPreferencesDto(
+    int MaxQuestions = 3,
+    int MaxNextActions = 3);
diff --git a/Journal.Core/Dtos/CommandDtos.cs b/Journal.Core/Dtos/CommandDtos.cs
index 03b6825..e979bfc 100644
--- a/Journal.Core/Dtos/CommandDtos.cs
+++ b/Journal.Core/Dtos/CommandDtos.cs
@@ -20,6 +20,9 @@ internal sealed record AiSummarizeEntryPayload(string Content, string? FileStem
 internal sealed record AiSummarizeAllPayload(List<string>? Entries);
 internal sealed record AiChatPayload(string Prompt);
 internal sealed record AiEmbedPayload(string Content);
+internal sealed record CoachDailyPayload(string? DateLocal = null, CoachPreferencesDto? Preferences = null, List<string>? RecentEntries = null, List<string>? RecentFragments = null);
+internal sealed record CoachEveningPayload(string? DateLocal = null, CoachPreferencesDto? Preferences = null, List<string>? RecentEntries = null, List<string>? RecentFragments = null);
+internal sealed record CoachWeeklyPayload(string? WeekStartLocal = null, string? WeekEndLocal = null, CoachPreferencesDto? Preferences = null, List<string>? RecentEntries = null, List<string>? RecentFragments = null);
 internal sealed record SpeechTranscribePayload(
     string? AudioBase64 = null,
     string? Audio_Base64 = null,
@@ -30,6 +33,9 @@ internal sealed record SpeechTranscribePayload(
     int? SimulateDelayMs = null,
     int? Simulate_Delay_Ms = null);
 internal sealed record S2TPollPayload(int? MaxItems = null);
+internal sealed record ConversationCreatePayload(string Title);
+internal sealed record ConversationUpdatePayload(string? Title);
+internal sealed record ConversationChatPayload(string ConversationId, string Prompt);
 internal sealed record SearchEntriesPayload(
     string? Query = null,
     string? Section = null,
diff --git a/Journal.Core/Dtos/ConversationDtos.cs b/Journal.Core/Dtos/ConversationDtos.cs
new file mode 100644
index 0000000..30b4aee
--- /dev/null
+++ b/Journal.Core/Dtos/ConversationDtos.cs
@@ -0,0 +1,28 @@
+using System.ComponentModel.DataAnnotations;
+
+namespace Journal.Core.Dtos;
+
+public sealed record ConversationDto(
+    Guid Id,
+    string Title,
+    DateTimeOffset CreatedAt,
+    DateTimeOffset UpdatedAt);
+
+public sealed record ConversationDetailDto(
+    Guid Id,
+    string Title,
+    IReadOnlyList<ConversationMessageDto> Messages,
+    DateTimeOffset CreatedAt,
+    DateTimeOffset UpdatedAt);
+
+public sealed record ConversationMessageDto(
+    Guid Id,
+    string Role,
+    string Text,
+    DateTimeOffset CreatedAt);
+
+public sealed record CreateConversationDto(
+    [Required] string Title);
+
+public sealed record UpdateConversationDto(
+    string? Title);
diff --git a/Journal.Core/Entry.cs b/Journal.Core/Entry.cs
index 8b0e6c1..bfc425d 100644
--- a/Journal.Core/Entry.cs
+++ b/Journal.Core/Entry.cs
@@ -9,6 +9,7 @@ using Journal.Core.Services.Database;
 using Journal.Core.Services.Entries;
 using Journal.Core.Services.Fragments;
 using Journal.Core.Services.Lists;
+using Journal.Core.Services.Conversations;
 using Journal.Core.Services.Logging;
 using Journal.Core.Services.Speech;
 using Journal.Core.Services.Todos;
@@ -29,6 +30,8 @@ public class Entry(
     IEntryFileService entryFiles,
     IListService lists,
     ITodoService todos,
+    ICoachService coach,
+    IConversationService conversations,
     CommandLogger logger)
 {
     private readonly IFragmentService _fragments = fragments;
@@ -43,6 +46,8 @@ public class Entry(
     private readonly IEntryFileService _entryFiles = entryFiles;
     private readonly IListService _lists = lists;
     private readonly ITodoService _todos = todos;
+    private readonly ICoachService _coach = coach;
+    private readonly IConversationService _conversations = conversations;
     private readonly CommandLogger _logger = logger;
     private static readonly HashSet<string> VaultSyncActions = new(StringComparer.Ordinal)
     {
@@ -61,7 +66,11 @@ public class Entry(
         "todos.delete",
         "todos.items.create",
         "todos.items.update",
-        "todos.items.delete"
+        "todos.items.delete",
+        "conversations.create",
+        "conversations.update",
+        "conversations.delete",
+        "conversations.chat"
     };
     private static readonly JsonSerializerOptions JsonOptions = new()
     {
@@ -303,6 +312,84 @@ public class Entry(
                         return Error("Missing or invalid payload");
                     result = await _ai.EmbedAsync(embedPayload.Content);
                     break;
+
+                // ── Coach ─────────────────────────────────────────
+                case "ai.coach.daily":
+                    var coachDailyPayload = DeserializePayload<CoachDailyPayload>(cmd.Payload);
+                    result = await _coach.DailyCheckInAsync(new CoachContextDto(
+                        DateLocal: coachDailyPayload?.DateLocal ?? DateTime.Now.ToString("yyyy-MM-dd"),
+                        RecentEntries: coachDailyPayload?.RecentEntries,
+                        RecentFragments: coachDailyPayload?.RecentFragments,
+                        Preferences: coachDailyPayload?.Preferences));
+                    break;
+                case "ai.coach.evening":
+                    var coachEveningPayload = DeserializePayload<CoachEveningPayload>(cmd.Payload);
+                    result = await _coach.EveningReviewAsync(new CoachContextDto(
+                        DateLocal: coachEveningPayload?.DateLocal ?? DateTime.Now.ToString("yyyy-MM-dd"),
+                        RecentEntries: coachEveningPayload?.RecentEntries,
+                        RecentFragments: coachEveningPayload?.RecentFragments,
+                        Preferences: coachEveningPayload?.Preferences));
+                    break;
+                case "ai.coach.weekly":
+                    var coachWeeklyPayload = DeserializePayload<CoachWeeklyPayload>(cmd.Payload);
+                    var now = DateTime.Now;
+                    var weekStart = now.AddDays(-(int)now.DayOfWeek + (int)DayOfWeek.Monday);
+                    result = await _coach.WeeklyReviewAsync(new CoachContextDto(
+                        DateLocal: now.ToString("yyyy-MM-dd"),
+                        WeekStartLocal: coachWeeklyPayload?.WeekStartLocal ?? weekStart.ToString("yyyy-MM-dd"),
+                        WeekEndLocal: coachWeeklyPayload?.WeekEndLocal ?? weekStart.AddDays(6).ToString("yyyy-MM-dd"),
+                        RecentEntries: coachWeeklyPayload?.RecentEntries,
+                        RecentFragments: coachWeeklyPayload?.RecentFragments,
+                        Preferences: coachWeeklyPayload?.Preferences));
+                    break;
+
+                // ── Conversations ──────────────────────────────────
+                case "conversations.list":
+                    result = _conversations.GetAll();
+                    break;
+                case "conversations.get":
+                    if (!Guid.TryParse(cmd.Id, out var getConvId))
+                        return Error("Invalid or missing id");
+                    result = _conversations.GetById(getConvId);
+                    break;
+                case "conversations.create":
+                    var convCreatePayload = DeserializePayload<ConversationCreatePayload>(cmd.Payload);
+                    if (convCreatePayload is null || string.IsNullOrWhiteSpace(convCreatePayload.Title))
+                        return Error("Missing or invalid payload");
+                    result = _conversations.Create(new CreateConversationDto(convCreatePayload.Title));
+                    break;
+                case "conversations.update":
+                    if (!Guid.TryParse(cmd.Id, out var updateConvId))
+                        return Error("Invalid or missing id");
+                    var convUpdatePayload = DeserializePayload<ConversationUpdatePayload>(cmd.Payload);
+                    if (convUpdatePayload is null)
+                        return Error("Missing or invalid payload");
+                    result = _conversations.Update(updateConvId, new UpdateConversationDto(convUpdatePayload.Title));
+                    break;
+                case "conversations.delete":
+                    if (!Guid.TryParse(cmd.Id, out var deleteConvId))
+                        return Error("Invalid or missing id");
+                    result = _conversations.Remove(deleteConvId);
+                    break;
+                case "conversations.chat":
+                    var convChatPayload = DeserializePayload<ConversationChatPayload>(cmd.Payload);
+                    if (convChatPayload is null || string.IsNullOrWhiteSpace(convChatPayload.Prompt)
+                        || !Guid.TryParse(convChatPayload.ConversationId, out var chatConvId))
+                        return Error("Missing or invalid payload");
+                    // Save user message
+                    var userMsg = _conversations.AddMessage(chatConvId, "user", convChatPayload.Prompt);
+                    // Build history from existing messages
+                    var history = _conversations.GetMessages(chatConvId)
+                        .Where(m => m.Id != userMsg.Id)
+                        .Select(m => (m.Role, m.Text))
+                        .ToList();
+                    // Get AI response with full conversation context
+                    var aiResponse = await _ai.ChatWithHistoryAsync(history, convChatPayload.Prompt);
+                    // Save AI response
+                    var assistantMsg = _conversations.AddMessage(chatConvId, "assistant", aiResponse);
+                    result = new { userMessage = userMsg, assistantMessage = assistantMsg };
+                    break;
+
                 case "speech.devices.list":
                     result = await _speech.ListDevicesAsync();
                     break;
diff --git a/Journal.Core/Models/Conversation.cs b/Journal.Core/Models/Conversation.cs
new file mode 100644
index 0000000..bd3f652
--- /dev/null
+++ b/Journal.Core/Models/Conversation.cs
@@ -0,0 +1,33 @@
+namespace Journal.Core.Models;
+
+public class Conversation
+{
+    public Guid Id { get; }
+    public string Title { get; set; }
+    public DateTimeOffset CreatedAt { get; set; }
+    public DateTimeOffset UpdatedAt { get; set; }
+
+    public Conversation(string title)
+    {
+        if (string.IsNullOrWhiteSpace(title))
+            throw new ArgumentException("Title is required", nameof(title));
+
+        Id = Guid.NewGuid();
+        Title = title.Trim();
+        CreatedAt = DateTimeOffset.Now;
+        UpdatedAt = CreatedAt;
+    }
+
+    public Conversation(Guid id, string title, DateTimeOffset createdAt, DateTimeOffset updatedAt)
+    {
+        if (id == Guid.Empty)
+            throw new ArgumentException("Id is required", nameof(id));
+        if (string.IsNullOrWhiteSpace(title))
+            throw new ArgumentException("Title is required", nameof(title));
+
+        Id = id;
+        Title = title.Trim();
+        CreatedAt = createdAt;
+        UpdatedAt = updatedAt;
+    }
+}
diff --git a/Journal.Core/Models/ConversationMessage.cs b/Journal.Core/Models/ConversationMessage.cs
new file mode 100644
index 0000000..36c6bba
--- /dev/null
+++ b/Journal.Core/Models/ConversationMessage.cs
@@ -0,0 +1,38 @@
+namespace Journal.Core.Models;
+
+public class ConversationMessage
+{
+    public Guid Id { get; }
+    public Guid ConversationId { get; }
+    public string Role { get; set; }
+    public string Text { get; set; }
+    public DateTimeOffset CreatedAt { get; set; }
+
+    public ConversationMessage(Guid conversationId, string role, string text)
+    {
+        if (conversationId == Guid.Empty)
+            throw new ArgumentException("ConversationId is required", nameof(conversationId));
+        if (string.IsNullOrWhiteSpace(role))
+            throw new ArgumentException("Role is required", nameof(role));
+        if (string.IsNullOrWhiteSpace(text))
+            throw new ArgumentException("Text is required", nameof(text));
+
+        Id = Guid.NewGuid();
+        ConversationId = conversationId;
+        Role = role.Trim();
+        Text = text;
+        CreatedAt = DateTimeOffset.Now;
+    }
+
+    public ConversationMessage(Guid id, Guid conversationId, string role, string text, DateTimeOffset createdAt)
+    {
+        if (id == Guid.Empty)
+            throw new ArgumentException("Id is required", nameof(id));
+
+        Id = id;
+        ConversationId = conversationId;
+        Role = role;
+        Text = text;
+        CreatedAt = createdAt;
+    }
+}
diff --git a/Journal.Core/Models/JournalConfig.cs b/Journal.Core/Models/JournalConfig.cs
index 3f81da5..7abcae6 100644
--- a/Journal.Core/Models/JournalConfig.cs
+++ b/Journal.Core/Models/JournalConfig.cs
@@ -24,4 +24,5 @@ public sealed record JournalConfig(
     string AiProvider,
     string PythonExecutable,
     string PythonAiSidecarPath,
-    int AiSidecarTimeoutMs);
+    int AiSidecarTimeoutMs,
+    string GgufModelPath);
diff --git a/Journal.Core/Repositories/IConversationRepository.cs b/Journal.Core/Repositories/IConversationRepository.cs
new file mode 100644
index 0000000..271ecb9
--- /dev/null
+++ b/Journal.Core/Repositories/IConversationRepository.cs
@@ -0,0 +1,14 @@
+using Journal.Core.Models;
+
+namespace Journal.Core.Repositories;
+
+public interface IConversationRepository
+{
+    List<Conversation> GetAll();
+    Conversation? GetById(Guid id);
+    void Add(Conversation conversation);
+    bool Update(Guid id, string? title = null);
+    bool Remove(Guid id);
+    void AddMessage(ConversationMessage message);
+    List<ConversationMessage> GetMessages(Guid conversationId);
+}
diff --git a/Journal.Core/Repositories/SqliteConversationRepository.cs b/Journal.Core/Repositories/SqliteConversationRepository.cs
new file mode 100644
index 0000000..ab85675
--- /dev/null
+++ b/Journal.Core/Repositories/SqliteConversationRepository.cs
@@ -0,0 +1,217 @@
+using Journal.Core.Models;
+using Journal.Core.Services.Database;
+using Microsoft.Data.Sqlite;
+
+namespace Journal.Core.Repositories;
+
+public sealed class SqliteConversationRepository(IDatabaseSessionService session) : IConversationRepository
+{
+    private readonly IDatabaseSessionService _session = session;
+
+    public List<Conversation> GetAll()
+    {
+        var conn = _session.GetConnection();
+        return ReadAll(conn);
+    }
+
+    public Conversation? GetById(Guid id)
+    {
+        var conn = _session.GetConnection();
+        return ReadById(conn, id);
+    }
+
+    public void Add(Conversation conversation)
+    {
+        ArgumentNullException.ThrowIfNull(conversation);
+        var conn = _session.GetConnection();
+        Insert(conn, conversation);
+    }
+
+    public bool Update(Guid id, string? title = null)
+    {
+        var conn = _session.GetConnection();
+        var existing = ReadById(conn, id);
+        if (existing is null)
+            return false;
+
+        if (title is not null)
+        {
+            if (string.IsNullOrWhiteSpace(title))
+                throw new ArgumentException("Title cannot be empty", nameof(title));
+            existing.Title = title.Trim();
+        }
+
+        existing.UpdatedAt = DateTimeOffset.Now;
+        UpdateRow(conn, existing);
+        return true;
+    }
+
+    public bool Remove(Guid id)
+    {
+        var conn = _session.GetConnection();
+        return Delete(conn, id);
+    }
+
+    public void AddMessage(ConversationMessage message)
+    {
+        ArgumentNullException.ThrowIfNull(message);
+        var conn = _session.GetConnection();
+        InsertMessage(conn, message);
+
+        // Touch conversation updated_at
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = "UPDATE conversations SET updated_at = @now WHERE guid = @guid;";
+        cmd.Parameters.AddWithValue("@now", DateTimeOffset.Now.ToString("O"));
+        cmd.Parameters.AddWithValue("@guid", message.ConversationId.ToString("D"));
+        cmd.ExecuteNonQuery();
+    }
+
+    public List<ConversationMessage> GetMessages(Guid conversationId)
+    {
+        var conn = _session.GetConnection();
+        return ReadMessages(conn, conversationId);
+    }
+
+    // ── Private helpers ──────────────────────────────────────────────
+
+    private static void Insert(SqliteConnection conn, Conversation c)
+    {
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = """
+            INSERT INTO conversations (guid, title, created_at, updated_at)
+            VALUES (@guid, @title, @createdAt, @updatedAt);
+            """;
+        cmd.Parameters.AddWithValue("@guid", c.Id.ToString("D"));
+        cmd.Parameters.AddWithValue("@title", c.Title);
+        cmd.Parameters.AddWithValue("@createdAt", c.CreatedAt.ToString("O"));
+        cmd.Parameters.AddWithValue("@updatedAt", c.UpdatedAt.ToString("O"));
+        cmd.ExecuteNonQuery();
+    }
+
+    private static void UpdateRow(SqliteConnection conn, Conversation c)
+    {
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = """
+            UPDATE conversations SET title = @title, updated_at = @updatedAt
+            WHERE guid = @guid;
+            """;
+        cmd.Parameters.AddWithValue("@guid", c.Id.ToString("D"));
+        cmd.Parameters.AddWithValue("@title", c.Title);
+        cmd.Parameters.AddWithValue("@updatedAt", c.UpdatedAt.ToString("O"));
+        cmd.ExecuteNonQuery();
+    }
+
+    private static bool Delete(SqliteConnection conn, Guid id)
+    {
+        using var tx = conn.BeginTransaction();
+
+        // Get the row id for cascade delete of messages
+        var rowId = GetRowId(conn, id);
+        if (rowId.HasValue)
+        {
+            using var delMsgs = conn.CreateCommand();
+            delMsgs.CommandText = "DELETE FROM conversation_messages WHERE conversation_id = @id;";
+            delMsgs.Parameters.AddWithValue("@id", rowId.Value);
+            delMsgs.ExecuteNonQuery();
+        }
+
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = "DELETE FROM conversations WHERE guid = @guid;";
+        cmd.Parameters.AddWithValue("@guid", id.ToString("D"));
+        var rows = cmd.ExecuteNonQuery();
+
+        tx.Commit();
+        return rows > 0;
+    }
+
+    private static long? GetRowId(SqliteConnection conn, Guid id)
+    {
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = "SELECT id FROM conversations WHERE guid = @guid;";
+        cmd.Parameters.AddWithValue("@guid", id.ToString("D"));
+        var result = cmd.ExecuteScalar();
+        return result is long rowId ? rowId : null;
+    }
+
+    private static Conversation? ReadById(SqliteConnection conn, Guid id)
+    {
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = "SELECT guid, title, created_at, updated_at FROM conversations WHERE guid = @guid;";
+        cmd.Parameters.AddWithValue("@guid", id.ToString("D"));
+
+        using var reader = cmd.ExecuteReader();
+        return reader.Read() ? MapConversation(reader) : null;
+    }
+
+    private static List<Conversation> ReadAll(SqliteConnection conn)
+    {
+        var results = new List<Conversation>();
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = "SELECT guid, title, created_at, updated_at FROM conversations ORDER BY updated_at DESC;";
+
+        using var reader = cmd.ExecuteReader();
+        while (reader.Read())
+            results.Add(MapConversation(reader));
+
+        return results;
+    }
+
+    private static void InsertMessage(SqliteConnection conn, ConversationMessage m)
+    {
+        var convRowId = GetRowId(conn, m.ConversationId)
+            ?? throw new InvalidOperationException($"Conversation {m.ConversationId} not found");
+
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = """
+            INSERT INTO conversation_messages (guid, conversation_id, role, text, created_at)
+            VALUES (@guid, @conversationId, @role, @text, @createdAt);
+            """;
+        cmd.Parameters.AddWithValue("@guid", m.Id.ToString("D"));
+        cmd.Parameters.AddWithValue("@conversationId", convRowId);
+        cmd.Parameters.AddWithValue("@role", m.Role);
+        cmd.Parameters.AddWithValue("@text", m.Text);
+        cmd.Parameters.AddWithValue("@createdAt", m.CreatedAt.ToString("O"));
+        cmd.ExecuteNonQuery();
+    }
+
+    private static List<ConversationMessage> ReadMessages(SqliteConnection conn, Guid conversationId)
+    {
+        var rowId = GetRowId(conn, conversationId);
+        if (!rowId.HasValue)
+            return [];
+
+        var results = new List<ConversationMessage>();
+        using var cmd = conn.CreateCommand();
+        cmd.CommandText = """
+            SELECT guid, role, text, created_at
+            FROM conversation_messages
+            WHERE conversation_id = @conversationId
+            ORDER BY created_at ASC;
+            """;
+        cmd.Parameters.AddWithValue("@conversationId", rowId.Value);
+
+        using var reader = cmd.ExecuteReader();
+        while (reader.Read())
+            results.Add(MapMessage(reader, conversationId));
+
+        return results;
+    }
+
+    private static Conversation MapConversation(SqliteDataReader reader)
+    {
+        var guid = Guid.Parse(reader.GetString(0));
+        var title = reader.GetString(1);
+        var createdAt = reader.IsDBNull(2) ? DateTimeOffset.MinValue : DateTimeOffset.Parse(reader.GetString(2));
+        var updatedAt = reader.IsDBNull(3) ? createdAt : DateTimeOffset.Parse(reader.GetString(3));
+        return new Conversation(guid, title, createdAt, updatedAt);
+    }
+
+    private static ConversationMessage MapMessage(SqliteDataReader reader, Guid conversationId)
+    {
+        var guid = Guid.Parse(reader.GetString(0));
+        var role = reader.GetString(1);
+        var text = reader.IsDBNull(2) ? "" : reader.GetString(2);
+        var createdAt = reader.IsDBNull(3) ? DateTimeOffset.MinValue : DateTimeOffset.Parse(reader.GetString(3));
+        return new ConversationMessage(guid, conversationId, role, text, createdAt);
+    }
+}
diff --git a/Journal.Core/ServiceCollectionExtensions.cs b/Journal.Core/ServiceCollectionExtensions.cs
index 1db977f..852cd18 100644
--- a/Journal.Core/ServiceCollectionExtensions.cs
+++ b/Journal.Core/ServiceCollectionExtensions.cs
@@ -9,6 +9,7 @@ using Journal.Core.Services.Lists;
 using Journal.Core.Services.Logging;
 using Journal.Core.Services.Sidecar;
 using Journal.Core.Services.Speech;
+using Journal.Core.Services.Conversations;
 using Journal.Core.Services.Todos;
 using Journal.Core.Services.Vault;
 
@@ -65,6 +66,9 @@ public static class ServiceCollectionExtensions
         services.AddSingleton<IListService, ListService>();
         services.AddSingleton<ITodoRepository, SqliteTodoRepository>();
         services.AddSingleton<ITodoService, TodoService>();
+        services.AddSingleton<ICoachService>(new DisabledCoachService());
+        services.AddSingleton<IConversationRepository, SqliteConversationRepository>();
+        services.AddSingleton<IConversationService, ConversationService>();
         services.AddSingleton<CommandLogger>();
         services.AddSingleton<SidecarCli>();
         return services;
diff --git a/Journal.Core/Services/Ai/DisabledAiService.cs b/Journal.Core/Services/Ai/DisabledAiService.cs
index d5a7ad6..c44443e 100644
--- a/Journal.Core/Services/Ai/DisabledAiService.cs
+++ b/Journal.Core/Services/Ai/DisabledAiService.cs
@@ -20,6 +20,9 @@ public sealed class DisabledAiService(string provider, string message = "AI prov
     public Task<string> ChatAsync(string prompt, CancellationToken cancellationToken = default) =>
         Task.FromResult(_message);
 
+    public Task<string> ChatWithHistoryAsync(IReadOnlyList<(string Role, string Text)> history, string prompt, CancellationToken cancellationToken = default) =>
+        Task.FromResult(_message);
+
     public Task<IReadOnlyList<double>> EmbedAsync(string content, CancellationToken cancellationToken = default) =>
         Task.FromResult<IReadOnlyList<double>>([]);
 }
diff --git a/Journal.Core/Services/Ai/DisabledCoachService.cs b/Journal.Core/Services/Ai/DisabledCoachService.cs
new file mode 100644
index 0000000..6b90fb9
--- /dev/null
+++ b/Journal.Core/Services/Ai/DisabledCoachService.cs
@@ -0,0 +1,26 @@
+using Journal.Core.Dtos;
+
+namespace Journal.Core.Services.Ai;
+
+public sealed class DisabledCoachService(string message = "Coach is not available. Set JOURNAL_AI_PROVIDER to enable.") : ICoachService
+{
+    private readonly string _message = message;
+
+    public Task<CoachPlanDto> DailyCheckInAsync(CoachContextDto context, CancellationToken cancellationToken = default)
+        => Task.FromResult(Disabled("daily_checkin"));
+
+    public Task<CoachPlanDto> EveningReviewAsync(CoachContextDto context, CancellationToken cancellationToken = default)
+        => Task.FromResult(Disabled("evening_review"));
+
+    public Task<CoachPlanDto> WeeklyReviewAsync(CoachContextDto context, CancellationToken cancellationToken = default)
+        => Task.FromResult(Disabled("weekly_review"));
+
+    private CoachPlanDto Disabled(string kind) => new(
+        Kind: kind,
+        Title: "Coach Disabled",
+        Summary: _message,
+        Questions: [],
+        SuggestedNextActions: [],
+        SuggestedTags: [],
+        Evidence: []);
+}
diff --git a/Journal.Core/Services/Ai/IAiService.cs b/Journal.Core/Services/Ai/IAiService.cs
index 5300641..0621e98 100644
--- a/Journal.Core/Services/Ai/IAiService.cs
+++ b/Journal.Core/Services/Ai/IAiService.cs
@@ -8,5 +8,6 @@ public interface IAiService
     Task<string> SummarizeEntryAsync(string content, string? fileStem = null, CancellationToken cancellationToken = default);
     Task<string> SummarizeAllAsync(IReadOnlyList<string> entries, CancellationToken cancellationToken = default);
     Task<string> ChatAsync(string prompt, CancellationToken cancellationToken = default);
+    Task<string> ChatWithHistoryAsync(IReadOnlyList<(string Role, string Text)> history, string prompt, CancellationToken cancellationToken = default);
     Task<IReadOnlyList<double>> EmbedAsync(string content, CancellationToken cancellationToken = default);
 }
diff --git a/Journal.Core/Services/Ai/ICoachService.cs b/Journal.Core/Services/Ai/ICoachService.cs
new file mode 100644
index 0000000..e2a63d4
--- /dev/null
+++ b/Journal.Core/Services/Ai/ICoachService.cs
@@ -0,0 +1,10 @@
+using Journal.Core.Dtos;
+
+namespace Journal.Core.Services.Ai;
+
+public interface ICoachService
+{
+    Task<CoachPlanDto> DailyCheckInAsync(CoachContextDto context, CancellationToken cancellationToken = default);
+    Task<CoachPlanDto> EveningReviewAsync(CoachContextDto context, CancellationToken cancellationToken = default);
+    Task<CoachPlanDto> WeeklyReviewAsync(CoachContextDto context, CancellationToken cancellationToken = default);
+}
diff --git a/Journal.Core/Services/Ai/PythonSidecarAiService.cs b/Journal.Core/Services/Ai/PythonSidecarAiService.cs
index daba179..b1c0474 100644
--- a/Journal.Core/Services/Ai/PythonSidecarAiService.cs
+++ b/Journal.Core/Services/Ai/PythonSidecarAiService.cs
@@ -61,6 +61,13 @@ public sealed class PythonSidecarAiService : IAiService
         return data?.GetString() ?? "";
     }
 
+    public Task<string> ChatWithHistoryAsync(IReadOnlyList<(string Role, string Text)> history,
+        string prompt, CancellationToken cancellationToken = default)
+    {
+        // Python sidecar does not support multi-turn — fall back to single-turn
+        return ChatAsync(prompt, cancellationToken);
+    }
+
     public async Task<IReadOnlyList<double>> EmbedAsync(string content, CancellationToken cancellationToken = default)
     {
         if (string.IsNullOrWhiteSpace(content))
diff --git a/Journal.Core/Services/Config/JournalConfigService.cs b/Journal.Core/Services/Config/JournalConfigService.cs
index 14e245a..d20f531 100644
--- a/Journal.Core/Services/Config/JournalConfigService.cs
+++ b/Journal.Core/Services/Config/JournalConfigService.cs
@@ -21,8 +21,8 @@ public sealed class JournalConfigService : IJournalConfigService
         if (nlpBackend is not ("auto" or "spacy" or "fallback"))
             nlpBackend = "auto";
 
-        var aiProvider = (Environment.GetEnvironmentVariable("JOURNAL_AI_PROVIDER") ?? "none").Trim().ToLowerInvariant();
-        if (aiProvider is not ("none" or "python-sidecar"))
+        var aiProvider = (Environment.GetEnvironmentVariable("JOURNAL_AI_PROVIDER") ?? "llamasharp").Trim().ToLowerInvariant();
+        if (aiProvider is not ("none" or "python-sidecar" or "llamasharp"))
             aiProvider = "none";
 
         var pythonExecutable = Environment.GetEnvironmentVariable("JOURNAL_PYTHON_EXE");
@@ -57,7 +57,8 @@ public sealed class JournalConfigService : IJournalConfigService
             AiProvider: aiProvider,
             PythonExecutable: pythonExecutable,
             PythonAiSidecarPath: pythonAiSidecarPath,
-            AiSidecarTimeoutMs: aiSidecarTimeoutMs);
+            AiSidecarTimeoutMs: aiSidecarTimeoutMs,
+            GgufModelPath: ResolveGgufModelPath(projectRoot));
     }
 
     private static string ResolveProjectRoot()
@@ -101,5 +102,22 @@ public sealed class JournalConfigService : IJournalConfigService
             return null;
         return int.TryParse(value, out var parsed) ? parsed : null;
     }
+
+    private static string ResolveGgufModelPath(string projectRoot)
+    {
+        var fromEnv = Environment.GetEnvironmentVariable("JOURNAL_GGUF_MODEL_PATH");
+        if (!string.IsNullOrWhiteSpace(fromEnv))
+            return Path.GetFullPath(fromEnv);
+
+        var modelsDir = Path.Combine(projectRoot, "models");
+        if (Directory.Exists(modelsDir))
+        {
+            var first = Directory.EnumerateFiles(modelsDir, "*.gguf").FirstOrDefault();
+            if (first is not null)
+                return Path.GetFullPath(first);
+        }
+
+        return Path.Combine(modelsDir, "model.gguf");
+    }
 }
 
diff --git a/Journal.Core/Services/Conversations/ConversationService.cs b/Journal.Core/Services/Conversations/ConversationService.cs
new file mode 100644
index 0000000..c1949f1
--- /dev/null
+++ b/Journal.Core/Services/Conversations/ConversationService.cs
@@ -0,0 +1,68 @@
+using System.ComponentModel.DataAnnotations;
+using Journal.Core.Dtos;
+using Journal.Core.Models;
+using Journal.Core.Repositories;
+
+namespace Journal.Core.Services.Conversations;
+
+public class ConversationService(IConversationRepository repo) : IConversationService
+{
+    private readonly IConversationRepository _repo = repo ?? throw new ArgumentNullException(nameof(repo));
+
+    private static ConversationDto MapSummary(Conversation c) => new(c.Id, c.Title, c.CreatedAt, c.UpdatedAt);
+
+    private static ConversationMessageDto MapMessage(ConversationMessage m) => new(m.Id, m.Role, m.Text, m.CreatedAt);
+
+    public List<ConversationDto> GetAll()
+    {
+        var items = _repo.GetAll();
+        return [.. items.Select(MapSummary)];
+    }
+
+    public ConversationDetailDto? GetById(Guid id)
+    {
+        var c = _repo.GetById(id);
+        if (c is null) return null;
+
+        var messages = _repo.GetMessages(id);
+        return new ConversationDetailDto(
+            c.Id, c.Title,
+            [.. messages.Select(MapMessage)],
+            c.CreatedAt, c.UpdatedAt);
+    }
+
+    public ConversationDto Create(CreateConversationDto dto)
+    {
+        ArgumentNullException.ThrowIfNull(dto);
+        var ctx = new ValidationContext(dto);
+        Validator.ValidateObject(dto, ctx, validateAllProperties: true);
+
+        var conversation = new Conversation(dto.Title);
+        _repo.Add(conversation);
+        return MapSummary(conversation);
+    }
+
+    public bool Update(Guid id, UpdateConversationDto dto)
+    {
+        ArgumentNullException.ThrowIfNull(dto);
+        if (dto.Title is not null && string.IsNullOrWhiteSpace(dto.Title))
+            throw new ValidationException("Title cannot be empty");
+
+        return _repo.Update(id, dto.Title?.Trim());
+    }
+
+    public bool Remove(Guid id) => _repo.Remove(id);
+
+    public ConversationMessageDto AddMessage(Guid conversationId, string role, string text)
+    {
+        var message = new ConversationMessage(conversationId, role, text);
+        _repo.AddMessage(message);
+        return MapMessage(message);
+    }
+
+    public List<ConversationMessageDto> GetMessages(Guid conversationId)
+    {
+        var messages = _repo.GetMessages(conversationId);
+        return [.. messages.Select(MapMessage)];
+    }
+}
diff --git a/Journal.Core/Services/Conversations/IConversationService.cs b/Journal.Core/Services/Conversations/IConversationService.cs
new file mode 100644
index 0000000..92c79b4
--- /dev/null
+++ b/Journal.Core/Services/Conversations/IConversationService.cs
@@ -0,0 +1,14 @@
+using Journal.Core.Dtos;
+
+namespace Journal.Core.Services.Conversations;
+
+public interface IConversationService
+{
+    List<ConversationDto> GetAll();
+    ConversationDetailDto? GetById(Guid id);
+    ConversationDto Create(CreateConversationDto dto);
+    bool Update(Guid id, UpdateConversationDto dto);
+    bool Remove(Guid id);
+    ConversationMessageDto AddMessage(Guid conversationId, string role, string text);
+    List<ConversationMessageDto> GetMessages(Guid conversationId);
+}
diff --git a/Journal.Core/Services/Database/JournalDatabaseService.cs b/Journal.Core/Services/Database/JournalDatabaseService.cs
index d762eab..b5eb46c 100644
--- a/Journal.Core/Services/Database/JournalDatabaseService.cs
+++ b/Journal.Core/Services/Database/JournalDatabaseService.cs
@@ -15,7 +15,7 @@ public sealed class JournalDatabaseService(IJournalConfigService config) : IJour
     private static readonly Lock SqliteInitLock = new();
     private static bool _sqliteInitialized;
     private static readonly IReadOnlyList<string> RequiredSchemaTables =
-        ["entries", "sections", "fragments", "tags", "fragment_tags", "lists", "todo_lists", "todo_items", "entry_documents"];
+        ["entries", "sections", "fragments", "tags", "fragment_tags", "lists", "todo_lists", "todo_items", "entry_documents", "conversations", "conversation_messages"];
 
     private readonly IJournalConfigService _config = config;
 
@@ -129,6 +129,26 @@ public sealed class JournalDatabaseService(IJournalConfigService config) : IJour
                     is_template INTEGER NOT NULL DEFAULT 0,
                     updated_at TEXT
                 );
+                """,
+            ["conversations"] = """
+                CREATE TABLE IF NOT EXISTS conversations (
+                    id INTEGER PRIMARY KEY AUTOINCREMENT,
+                    guid TEXT UNIQUE,
+                    title TEXT NOT NULL,
+                    created_at TEXT,
+                    updated_at TEXT
+                );
+                """,
+            ["conversation_messages"] = """
+                CREATE TABLE IF NOT EXISTS conversation_messages (
+                    id INTEGER PRIMARY KEY AUTOINCREMENT,
+                    guid TEXT UNIQUE,
+                    conversation_id INTEGER NOT NULL,
+                    role TEXT NOT NULL,
+                    text TEXT NOT NULL,
+                    created_at TEXT,
+                    FOREIGN KEY (conversation_id) REFERENCES conversations (id)
+                );
                 """
         };
     }
diff --git a/Journal.Sidecar/App.cs b/Journal.Sidecar/App.cs
index e72ae6a..95f3f3e 100644
--- a/Journal.Sidecar/App.cs
+++ b/Journal.Sidecar/App.cs
@@ -1,4 +1,5 @@
 using Microsoft.Extensions.DependencyInjection;
+using Journal.AI;
 using Journal.Core;
 using Journal.Core.Services.Speech;
 using Journal.Core.Services.Sidecar;
@@ -9,6 +10,7 @@ Console.InputEncoding = System.Text.Encoding.UTF8;
 
 var services = new ServiceCollection();
 services.AddFragmentServices();
+services.AddLlamaSharpServices();
 services.AddSingleton<IS2TService, LocalWhisperS2TService>();
 services.AddSingleton<Entry>();
 var provider = services.BuildServiceProvider();
diff --git a/Journal.Sidecar/Journal.Sidecar.csproj b/Journal.Sidecar/Journal.Sidecar.csproj
index 8b95a51..e9b9245 100644
--- a/Journal.Sidecar/Journal.Sidecar.csproj
+++ b/Journal.Sidecar/Journal.Sidecar.csproj
@@ -10,6 +10,7 @@
   </PropertyGroup>
 
   <ItemGroup>
+    <ProjectReference Include="..\Journal.AI\Journal.AI.csproj" />
     <ProjectReference Include="..\Journal.Core\Journal.Core.csproj" />
   </ItemGroup>
 
diff --git a/Journal.Sidecar/LocalWhisperS2TService.cs b/Journal.Sidecar/LocalWhisperS2TService.cs
index 26fe532..b53ecb9 100644
--- a/Journal.Sidecar/LocalWhisperS2TService.cs
+++ b/Journal.Sidecar/LocalWhisperS2TService.cs
@@ -16,8 +16,8 @@ public sealed class LocalWhisperS2TService : IS2TService, IDisposable
     private const int MaxBufferedItems = 256;
     private const int SilenceRmsThreshold = 150;
 
-    private readonly object _sync = new();
-    private readonly object _segmentLock = new();
+    private readonly Lock _sync = new();
+    private readonly Lock _segmentLock = new();
     private readonly ConcurrentQueue<string> _transcripts = new();
 
     private WaveInEvent? _waveIn;
diff --git a/Journal.SmokeTests/GlobalUsings.cs b/Journal.SmokeTests/GlobalUsings.cs
index 57dccd9..b94867a 100644
--- a/Journal.SmokeTests/GlobalUsings.cs
+++ b/Journal.SmokeTests/GlobalUsings.cs
@@ -15,4 +15,5 @@ global using Journal.Core.Services.Speech;
 global using Journal.Core.Services.Sidecar;
 global using Journal.Core.Services.Lists;
 global using Journal.Core.Services.Todos;
+global using Journal.Core.Services.Conversations;
 global using Journal.Core.Services.Vault;
diff --git a/Journal.SmokeTests/Program.Shared.cs b/Journal.SmokeTests/Program.Shared.cs
index 09f10b1..1f07488 100644
--- a/Journal.SmokeTests/Program.Shared.cs
+++ b/Journal.SmokeTests/Program.Shared.cs
@@ -25,9 +25,12 @@ internal static partial class Program
             config,
             new DisabledAiService("none"),
             new DisabledSpeechBridgeService("none"),
+            new DisabledS2TService(),
             new EntryFileService(entryRepo),
             new ListService(new SqliteListRepository(session)),
             new TodoService(new SqliteTodoRepository(session)),
+            new DisabledCoachService(),
+            new ConversationService(new SqliteConversationRepository(session)),
             new CommandLogger());
     }
 
diff --git a/Journal.SmokeTests/Program.VaultTests.cs b/Journal.SmokeTests/Program.VaultTests.cs
index a625d6b..9455be4 100644
--- a/Journal.SmokeTests/Program.VaultTests.cs
+++ b/Journal.SmokeTests/Program.VaultTests.cs
@@ -437,9 +437,12 @@ internal static partial class Program
             config,
             new DisabledAiService("none"),
             new DisabledSpeechBridgeService("none"),
+            new DisabledS2TService(),
             entryFiles,
             new ListService(new SqliteListRepository(session)),
             new TodoService(new SqliteTodoRepository(session)),
+            new DisabledCoachService(),
+            new ConversationService(new SqliteConversationRepository(session)),
             new CommandLogger());
 
         try
diff --git a/Journal.WebGateway/Journal.WebGateway.csproj b/Journal.WebGateway/Journal.WebGateway.csproj
index 511c2f0..f4e284d 100644
--- a/Journal.WebGateway/Journal.WebGateway.csproj
+++ b/Journal.WebGateway/Journal.WebGateway.csproj
@@ -7,6 +7,7 @@
   </PropertyGroup>
 
   <ItemGroup>
+    <ProjectReference Include="..\Journal.AI\Journal.AI.csproj" />
     <ProjectReference Include="..\Journal.Core\Journal.Core.csproj" />
   </ItemGroup>
 
diff --git a/Journal.WebGateway/Program.cs b/Journal.WebGateway/Program.cs
index fca14ce..4500445 100644
--- a/Journal.WebGateway/Program.cs
+++ b/Journal.WebGateway/Program.cs
@@ -1,5 +1,6 @@
 using System.Text.Json;
 using System.Text.Json.Serialization;
+using Journal.AI;
 using Journal.Core;
 using Microsoft.Extensions.FileProviders;
 
@@ -17,6 +18,7 @@ var webDistPath = ResolveWebDist(repoRoot);
 var builder = WebApplication.CreateBuilder(args);
 
 builder.Services.AddFragmentServices();
+builder.Services.AddLlamaSharpServices();
 builder.Services.AddSingleton<Entry>();
 builder.Services.AddSingleton(new SidecarRootState(repoRoot));
 builder.Services.AddSingleton(new WebUiState(webDistPath));
diff --git a/Journal.slnx b/Journal.slnx
index 090dfed..10b89d0 100644
--- a/Journal.slnx
+++ b/Journal.slnx
@@ -1,4 +1,5 @@
 <Solution>
+  <Project Path="Journal.AI/Journal.AI.csproj" />
   <Project Path="Journal.Core/Journal.Core.csproj" />
   <Project Path="Journal.Sidecar/Journal.Sidecar.csproj" />
   <Project Path="Journal.SmokeTests/Journal.SmokeTests.csproj" />
diff --git a/docs/frontend-csharp-backend-wiring.md b/docs/frontend-csharp-backend-wiring.md
deleted file mode 100644
index 2dd6cce..0000000
--- a/docs/frontend-csharp-backend-wiring.md
+++ /dev/null
@@ -1,218 +0,0 @@
-# Wiring Frontend to the C# Backend
-
-This document explains how to connect the `Journal.App` frontend to the C# backend in this repository.
-
-## Current Backend Reality
-
-In this repo today, the C# backend projects in `Journal.slnx` are:
-
-- `Journal.Core`
-- `Journal.Sidecar`
-- `Journal.SmokeTests`
-
-There is currently **no** `Journal.Api` project in the solution file, so the primary integration path is:
-
-- Frontend (Svelte/Tauri) -> Tauri bridge -> `Journal.Sidecar` (stdin/stdout JSON protocol)
-
-## Command Protocol (C#)
-
-`Journal.Core.Entry.HandleCommandAsync` accepts a JSON command envelope and returns:
-
-- success: `{ "ok": true, "data": ... }`
-- failure: `{ "ok": false, "error": "..." }`
-
-Command model (`Journal.Core/Models/Command.cs`):
-
-```json
-{
-  "action": "entries.list",
-  "correlationId": "optional-string",
-  "id": "optional",
-  "type": "optional",
-  "tag": "optional",
-  "payload": {}
-}
-```
-
-Useful actions for frontend wiring:
-
-- `entries.list`
-- `entries.load`
-- `entries.save`
-- `search.entries`
-- `vault.load_all`
-- `vault.save_current_month`
-- `db.status`
-- `db.hydrate_workspace`
-
-## Recommended Integration (Sidecar Bridge)
-
-Use a small frontend client that sends commands through one bridge function. The bridge can be backed by:
-
-- a Tauri command that talks to a managed sidecar process, or
-- a local HTTP adapter (if you add one).
-
-### 1. Define shared frontend command/response types
-
-Create `Journal.App/src/lib/backend/types.ts`:
-
-```ts
-export type BackendCommand = {
-  action: string;
-  correlationId?: string;
-  id?: string;
-  type?: string;
-  tag?: string;
-  payload?: unknown;
-};
-
-export type BackendOk<T> = { ok: true; data: T };
-export type BackendErr = { ok: false; error: string };
-export type BackendResponse<T> = BackendOk<T> | BackendErr;
-```
-
-### 2. Create one backend client entrypoint
-
-Create `Journal.App/src/lib/backend/client.ts`:
-
-```ts
-import { invoke } from "@tauri-apps/api/core";
-import type { BackendCommand, BackendResponse } from "./types";
-
-export async function sendCommand<T>(command: BackendCommand): Promise<T> {
-  const response = await invoke<BackendResponse<T>>("sidecar_command", { command });
-
-  if (!response.ok) {
-    throw new Error(response.error || "Backend command failed");
-  }
-
-  return response.data;
-}
-```
-
-This keeps all UI code backend-agnostic.
-
-### 3. Build domain helpers (entries example)
-
-Create `Journal.App/src/lib/backend/entries.ts`:
-
-```ts
-import { sendCommand } from "./client";
-
-export async function listEntries(dataDirectory?: string) {
-  return sendCommand<string[]>({
-    action: "entries.list",
-    payload: { dataDirectory }
-  });
-}
-
-export async function loadEntry(filePath: string) {
-  return sendCommand<{ filePath: string; content: string; section?: string }>({
-    action: "entries.load",
-    payload: { filePath }
-  });
-}
-
-export async function saveEntry(args: {
-  filePath?: string;
-  content: string;
-  title?: string;
-  section?: string;
-  date?: string;
-}) {
-  return sendCommand<{ filePath: string }>({
-    action: "entries.save",
-    payload: args
-  });
-}
-```
-
-### 4. Use client in UI state
-
-In page/component code:
-
-- on panel item click: call `loadEntry(filePath)`
-- on editor save button: call `saveEntry({ filePath, content })`
-- on app init: call `listEntries()` to populate list
-
-## Tauri Bridge Notes
-
-Your frontend should not spawn/process-manage the sidecar directly. Keep that in the Tauri layer.
-
-Bridge responsibilities:
-
-- start and keep one sidecar process alive
-- write command JSON lines to sidecar stdin
-- read stdout lines and map responses by `correlationId`
-- return parsed response to frontend
-- restart sidecar if it crashes
-
-If you have not implemented this yet, create one Tauri command such as:
-
-- `sidecar_command(command)`
-
-and route all frontend calls through it.
-
-## Vault/Auth Flow
-
-Recommended startup sequence:
-
-1. Prompt for vault password in UI.
-2. Call `vault.load_all` (or `db.hydrate_workspace`) once.
-3. Backend stores session password (`DatabaseSessionService`) for subsequent commands.
-4. Continue with `entries.list`, `entries.load`, etc.
-
-Do not store raw vault password in long-lived frontend state.
-
-## Error Handling Pattern
-
-Always normalize backend errors in one place:
-
-- backend client throws `Error(message)` when `ok: false`
-- UI catches and displays your custom modal
-- include `correlationId` on commands for tracing/logging
-
-## Optional HTTP Path (If You Add Journal.Api)
-
-If you later add `Journal.Api` with `POST /api/command`, keep the same command envelope and swap transport only:
-
-- replace `invoke("sidecar_command", ...)` with `fetch("/api/command", ...)`
-- keep `sendCommand` interface unchanged
-
-That lets UI code remain identical.
-
-## Minimal Next Steps
-
-1. Add `src/lib/backend/types.ts`, `client.ts`, `entries.ts`.
-2. Wire `EditorPanel` save button to `entries.save`.
-3. Wire `SidePanel` item load to `entries.load`.
-4. Add vault unlock modal + `vault.load_all` on startup.
-5. Keep all backend calls behind `sendCommand` only.
-
-## Frontend Store Architecture (Current)
-
-Current frontend uses feature stores in `Journal.App/src/lib/stores/`:
-
-- `entries.ts` -> `entriesStore`
-- `fragments.ts` -> `fragmentsStore`
-- `todos.ts` -> `todoListsStore`, `todosStore`
-- `lists.ts` -> `listsStore`
-- `settings.ts` -> `settingsTags`, `settingsFragmentTypes`
-
-Current pattern is store-first for most feature CRUD and parsing (especially fragments and todos), with UI components invoking store helpers.
-
-## State/CRUD Gaps Still Needed
-
-To fully standardize state management:
-
-1. Move settings add/edit/remove logic into `settings.ts` helper functions (currently in route component code).
-2. Add full CRUD helpers for `entries.ts` and `lists.ts` (update/remove/reorder, not only draft creation).
-3. Make todo list metadata + todo items update atomically through a single store API wrapper.
-4. Move calendar-created entries out of local component state into a dedicated calendar store.
-5. Add persistence/hydration strategy between stores and backend (`entries.load/save`, `vault.load_all`, etc.).
-
-## Recommended Rule
-
-- Keep all feature data mutations in store helper APIs.
-- Keep route/component files focused on view state and command orchestration.
-- Keep backend transport (`sendCommand`) separate from pure local store mutation helpers, then compose both in thin feature services.