diff --git a/Journal.App/src/lib/components/SidePanel.svelte b/Journal.App/src/lib/components/SidePanel.svelte
index 124cd41..4107835 100644
--- a/Journal.App/src/lib/components/SidePanel.svelte
+++ b/Journal.App/src/lib/components/SidePanel.svelte
@@ -9,6 +9,7 @@
   import { createFragmentDraft, fragmentsStore, serializeFragment } from "$lib/stores/fragments";
   import { createListDraft, createListFromLabel, listsStore } from "$lib/stores/lists";
   import { createTodoListDraft, createTodoListFromLabel, serializeTodoList, todoListsStore, todosStore } from "$lib/stores/todos";
+  import { extractEntryTags } from "$lib/utils/metadata";
 
   export let activeSection = "entries";
   export let activeDocumentId = "";
@@ -234,6 +235,12 @@
     return tokens.some((token) => lower.includes(token));
   }
 
+  function matchesTags(itemTags: string[] | undefined, tagTokens: string[]): boolean {
+    if (tagTokens.length === 0) return true;
+    const normalized = (itemTags ?? []).map((tag) => tag.toLowerCase().trim()).filter(Boolean);
+    return tagTokens.some((token) => normalized.includes(token));
+  }
+
   async function refreshCalendarTimeline(): Promise<void> {
     calendarBusy = true;
     calendarError = "";
@@ -247,11 +254,7 @@
       const { startDate, endDate } = getActiveDateRange();
       const entryItems = await searchEntriesAsItems({
         dataDirectory,
-        startDate,
-        endDate,
-        query: calendarQuery.trim() || undefined,
-        tags: parseCsv(calendarTags),
-        types: parseCsv(calendarTypes)
+        query: calendarQuery.trim() || undefined
       });
 
       const [fragmentDtos, listDtos, todoDtos] = await Promise.all([
@@ -266,24 +269,24 @@
       const hasTypeFilter = typeTokens.length > 0;
 
       const fragmentItems = fragmentDtos
-        .map(toFragmentTimelineItem)
-        .filter((item) => {
-          const date = item.sortDate ? parseIsoDate(item.sortDate) : null;
+        .filter((fragment) => {
+          const date = parseIsoDate(fragment.time);
           if (!date || !isWithinRange(date, startDate, endDate)) return false;
-          if (!matchesTextQuery(item.initialContent, query)) return false;
-          if (!matchesAnyToken(`${item.label}\n${item.initialContent}`, tagTokens)) return false;
-          if (hasTypeFilter && !matchesAnyToken(`${item.label}\n${item.initialContent}`, typeTokens)) return false;
+          if (!matchesTextQuery(fragment.description, query)) return false;
+          if (!matchesTags(fragment.tags, tagTokens)) return false;
+          if (hasTypeFilter && !matchesAnyToken(fragment.type ?? "", typeTokens)) return false;
           return true;
-        });
+        })
+        .map(toFragmentTimelineItem);
 
       const listItems = listDtos
         .map(toListTimelineItem)
         .filter((item) => {
           if (hasTypeFilter) return false;
+          if (tagTokens.length > 0) return false;
           const date = item.sortDate ? parseIsoDate(item.sortDate) : null;
           if (!date || !isWithinRange(date, startDate, endDate)) return false;
           if (!matchesTextQuery(item.initialContent, query) && !matchesTextQuery(item.label, query)) return false;
-          if (!matchesAnyToken(`${item.label}\n${item.initialContent}`, tagTokens)) return false;
           return true;
         });
 
@@ -291,10 +294,10 @@
         .map(toTodoTimelineItem)
         .filter((item) => {
           if (hasTypeFilter) return false;
+          if (tagTokens.length > 0) return false;
           const date = item.sortDate ? parseIsoDate(item.sortDate) : null;
           if (!date || !isWithinRange(date, startDate, endDate)) return false;
           if (!matchesTextQuery(item.initialContent, query) && !matchesTextQuery(item.label, query)) return false;
-          if (!matchesAnyToken(`${item.label}\n${item.initialContent}`, tagTokens)) return false;
           return true;
         });
 
@@ -311,7 +314,10 @@
         })
         .filter((item) => {
           if (hasTypeFilter) return false;
-          if (!matchesAnyToken(`${item.label}\n${item.initialContent}`, tagTokens)) return false;
+          if (!matchesTags(extractEntryTags(item.initialContent), tagTokens)) return false;
+          if (!matchesTextQuery(item.initialContent, query) && !matchesTextQuery(item.label, query)) return false;
+          const date = item.sortDate ? parseIsoDate(item.sortDate) : null;
+          if (date && !isWithinRange(date, startDate, endDate)) return false;
           return true;
         });
 
diff --git a/Journal.App/src/lib/components/editor/MarkdownEditor.svelte b/Journal.App/src/lib/components/editor/MarkdownEditor.svelte
index 88e906f..e810df1 100644
--- a/Journal.App/src/lib/components/editor/MarkdownEditor.svelte
+++ b/Journal.App/src/lib/components/editor/MarkdownEditor.svelte
@@ -226,6 +226,23 @@
     attachmentModalOpen = false;
   }
 
+  function insertTagToken() {
+    if (!editorInput) return;
+    const current = markdownText;
+    const start = editorInput.selectionStart ?? 0;
+    const end = editorInput.selectionEnd ?? start;
+    const selected = current.slice(start, end);
+    const insertion = selected ? `[[${selected}]]` : "[[]]";
+    const next = `${current.slice(0, start)}${insertion}${current.slice(end)}`;
+    updateDraft(next);
+    queueMicrotask(() => {
+      if (!editorInput) return;
+      const cursor = selected ? start + insertion.length : start + 2;
+      editorInput.focus();
+      editorInput.setSelectionRange(cursor, cursor);
+    });
+  }
+
   function resolveJournalLinkTarget(targetId: string): { id: string; label: string; initialContent: string } | null {
     if (!targetId) return null;
 
@@ -442,6 +459,7 @@
       onBold={() => applyWrap("**")}
       onItalic={() => applyWrap("*")}
       onUnderline={() => applyWrap("++")}
+      onTag={insertTagToken}
       onLink={insertLink}
       onToggleUl={() => toggleListMode("ul")}
       onToggleOl={() => toggleListMode("ol")}
diff --git a/Journal.App/src/lib/components/editor/MarkdownToolbar.svelte b/Journal.App/src/lib/components/editor/MarkdownToolbar.svelte
index 9e5b515..93afed7 100644
--- a/Journal.App/src/lib/components/editor/MarkdownToolbar.svelte
+++ b/Journal.App/src/lib/components/editor/MarkdownToolbar.svelte
@@ -14,6 +14,7 @@
   export let onBold: () => void = () => {};
   export let onItalic: () => void = () => {};
   export let onUnderline: () => void = () => {};
+  export let onTag: () => void = () => {};
   export let onLink: () => void = () => {};
   export let onToggleUl: () => void = () => {};
   export let onToggleOl: () => void = () => {};
@@ -142,6 +143,9 @@
     <button type="button" class="toolbar-btn toolbar-icon-btn" on:click={onUnderline} aria-label="Underline" title="Underline">
       <span class="material-symbols-outlined" aria-hidden="true">format_underlined</span>
     </button>
+    <button type="button" class="toolbar-btn toolbar-icon-btn" on:click={onTag} aria-label="Tag" title="Tag [[...]]">
+      <span class="material-symbols-outlined" aria-hidden="true">sell</span>
+    </button>
     <button type="button" class="toolbar-btn toolbar-icon-btn" on:click={onLink} aria-label="Link" title="Link">
       <span class="material-symbols-outlined" aria-hidden="true">link</span>
     </button>
diff --git a/Journal.App/src/lib/utils/metadata.ts b/Journal.App/src/lib/utils/metadata.ts
new file mode 100644
index 0000000..f77e330
--- /dev/null
+++ b/Journal.App/src/lib/utils/metadata.ts
@@ -0,0 +1,153 @@
+function normalizeTags(tags: string[]): string[] {
+  const seen = new Set<string>();
+  const result: string[] = [];
+  for (const tag of tags) {
+    const normalized = tag.trim();
+    if (!normalized) continue;
+    const key = normalized.toLowerCase();
+    if (seen.has(key)) continue;
+    seen.add(key);
+    result.push(normalized);
+  }
+  return result;
+}
+
+function splitFrontmatter(content: string): { frontmatter: string | null; body: string } {
+  const normalized = (content ?? "").replace(/\r\n/g, "\n");
+  if (!normalized.startsWith("---\n")) {
+    return { frontmatter: null, body: normalized };
+  }
+
+  const closingIndex = normalized.indexOf("\n---", 4);
+  if (closingIndex === -1) {
+    return { frontmatter: null, body: normalized };
+  }
+
+  const frontmatter = normalized.slice(4, closingIndex).trim();
+  const bodyStart = closingIndex + "\n---".length;
+  const body = normalized.slice(bodyStart).replace(/^\n/, "");
+  return { frontmatter, body };
+}
+
+function parseTagsValue(rawValue: string): string[] {
+  const value = rawValue.trim();
+  if (!value) return [];
+
+  if (value.startsWith("[") && value.endsWith("]")) {
+    return normalizeTags(
+      value
+        .slice(1, -1)
+        .split(",")
+        .map((token) => token.trim().replace(/^["']|["']$/g, ""))
+    );
+  }
+
+  return normalizeTags(
+    value
+      .split(",")
+      .map((token) => token.trim().replace(/^["']|["']$/g, ""))
+  );
+}
+
+function formatTagsValue(tags: string[]): string {
+  const normalized = normalizeTags(tags);
+  if (!normalized.length) return "";
+  return `[${normalized.join(", ")}]`;
+}
+
+export function parseTagsFromMarkdown(content: string): string[] {
+  const { frontmatter } = splitFrontmatter(content);
+  if (!frontmatter) return [];
+
+  const line = frontmatter.split("\n").find((entry) => /^\s*tags\s*:/i.test(entry));
+  if (!line) return [];
+  const value = line.replace(/^\s*tags\s*:/i, "");
+  return parseTagsValue(value);
+}
+
+export function stripFrontmatter(content: string): string {
+  return splitFrontmatter(content).body;
+}
+
+export function setTagsInMarkdown(content: string, tags: string[]): string {
+  const normalizedBody = (content ?? "").replace(/\r\n/g, "\n");
+  const normalizedTags = normalizeTags(tags);
+  const tagsLine = normalizedTags.length > 0 ? `tags: ${formatTagsValue(normalizedTags)}` : "";
+  const { frontmatter, body } = splitFrontmatter(normalizedBody);
+
+  if (!frontmatter) {
+    if (!tagsLine) return normalizedBody;
+    const trimmedBody = body.replace(/^\n+/, "");
+    return `---\n${tagsLine}\n---\n\n${trimmedBody}`;
+  }
+
+  const lines = frontmatter
+    .split("\n")
+    .map((line) => line.trimEnd())
+    .filter((line) => !/^\s*tags\s*:/i.test(line));
+
+  if (tagsLine) {
+    lines.unshift(tagsLine);
+  }
+
+  if (lines.length === 0) {
+    return body;
+  }
+
+  return `---\n${lines.join("\n")}\n---\n\n${body}`;
+}
+
+export function extractBracketTags(content: string): string[] {
+  const normalized = (content ?? "").replace(/\r\n/g, "\n");
+  const matches = normalized.matchAll(/\[\[([^\]]+)\]\]/g);
+  const tokens: string[] = [];
+  for (const match of matches) {
+    const raw = (match[1] ?? "").trim();
+    if (!raw) continue;
+    tokens.push(
+      ...raw
+        .split(",")
+        .map((token) => token.trim())
+        .filter(Boolean)
+    );
+  }
+  return normalizeTags(tokens);
+}
+
+export function extractTagsFromTagsSection(content: string): string[] {
+  const normalized = (content ?? "").replace(/\r\n/g, "\n");
+  const lines = normalized.split("\n");
+  const collected: string[] = [];
+
+  let inTagsSection = false;
+  for (const rawLine of lines) {
+    const line = rawLine.trim();
+    if (!inTagsSection) {
+      if (/^#{1,6}\s+tags\s*$/i.test(line)) {
+        inTagsSection = true;
+      }
+      continue;
+    }
+
+    if (!line) break;
+    if (/^#{1,6}\s+/.test(line)) break;
+
+    const cleaned = line.replace(/^[-*+]\s+/, "");
+    collected.push(
+      ...cleaned
+        .split(",")
+        .map((token) => token.trim())
+        .filter(Boolean)
+    );
+  }
+
+  return normalizeTags(collected);
+}
+
+export function extractEntryTags(content: string): string[] {
+  return normalizeTags([
+    ...parseTagsFromMarkdown(content),
+    ...extractBracketTags(content),
+    ...extractTagsFromTagsSection(content)
+  ]);
+}