diff --git a/CHANGELOG.md b/CHANGELOG.md
index 195dab8..25f2e26 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -36,6 +36,7 @@
 - Tables: insert via size picker, Word-style row/column drag-resize, add / delete rows & columns, delete table, cell borders, merge cells and split cells (N×M, Word/LibreOffice-style), cell background shading, header-row toggle (bold + shading); a table splits cleanly across page boundaries
 - Images: inline or floating with text wrap (left / right / top-bottom), resize handles, rotation, live size badge; insert via toolbar, drag-and-drop, or paste
 - Special characters picker
+- Table of contents: generated from headings (H1–H3) with live page numbers and dot leaders, click an entry to jump to its heading; round-trips to ODF `text:table-of-content` and a Word TOC field
 - Hyperlinks: create / edit / remove (toolbar + Ctrl+K), Ctrl/Cmd+click to open, hover hint showing the URL; ODF `text:a` round-trip
 - Manual page break (Ctrl+Enter); round-trips to ODF `fo:break-before`
 
@@ -70,7 +71,6 @@ Planned word-processor features (to match Word/LibreOffice):
 - Footnotes / endnotes (currently dropped on import)
 - Clear formatting (remove all marks)
 - Multi-column (newspaper) layout
-- Table of contents (generated from headings)
 - Comments / annotations (currently dropped on import)
 - Horizontal rule
 - Page numbering options (start value / format) + different first-page header
diff --git a/src/lib/components/ToolbarExpanded.svelte b/src/lib/components/ToolbarExpanded.svelte
index 26a1c11..0253823 100644
--- a/src/lib/components/ToolbarExpanded.svelte
+++ b/src/lib/components/ToolbarExpanded.svelte
@@ -663,6 +663,12 @@
     editor.chain().focus().setTextSelection(range).insertTable({ rows, cols, withHeaderRow: false }).run();
   }
 
+  // --- Table of contents insertion (tableOfContents.ts) ---
+  function insertToc() {
+    if (!editor || hfActive) return; // body-only; the HF schema has no TOC node
+    editor.chain().focus().setTableOfContents().run();
+  }
+
   // --- Special character insertion (SpecialCharPicker.svelte) ---
   let specialCharOpen = $state(false);
 
@@ -1225,6 +1231,17 @@
         style="display:none"
         onchange={onImageFile}
       />
+      <button
+        onclick={insertToc}
+        disabled={!!hfActive}
+        title={hfActive ? 'A table of contents is not available in headers/footers' : 'Insert table of contents'}
+        aria-label="Insert table of contents"
+      >
+        <svg width="16" height="16" viewBox="0 0 16 16" fill="none" aria-hidden="true">
+          <path d="M2 3.5h6M2 6.5h8M2 9.5h5M2 12.5h7" stroke="currentColor" stroke-width="1.3" stroke-linecap="round" />
+          <path d="M12.5 3.5h1.5M13.5 6.5H14M12 9.5h2M12.5 12.5H14" stroke="currentColor" stroke-width="1.3" stroke-linecap="round" />
+        </svg>
+      </button>
       <div class="link-wrap" use:linkClickOutside>
         <button
           class:active={isLink}
diff --git a/src/lib/editor/extensions.ts b/src/lib/editor/extensions.ts
index 604a0cb..686f81a 100644
--- a/src/lib/editor/extensions.ts
+++ b/src/lib/editor/extensions.ts
@@ -38,6 +38,7 @@ import { TableCellBackground } from './extensions/tableCellBackground';
 import { TableHeaderRow } from './extensions/tableHeaderRow';
 import { TrailingNode } from './extensions/trailingNode';
 import { Image } from './extensions/image';
+import { TableOfContents } from './extensions/tableOfContents';
 
 export const extensions = [
   Document,
@@ -65,6 +66,9 @@ export const extensions = [
   // Inline, as-character image; round-trips to ODF <draw:frame>/<draw:image>
   // (export/odt.ts replaceImages/applyImages, import/odt.ts).
   Image,
+  // Generated table of contents from headings; round-trips to ODF
+  // <text:table-of-content> (export/odt.ts, import/odt.ts) and a DOCX TOC field.
+  TableOfContents,
   LineHeight,
   ParagraphSpacing,
   PageBreak,
diff --git a/src/lib/editor/extensions/pageBreaks.ts b/src/lib/editor/extensions/pageBreaks.ts
index f0e9afa..15f0fb8 100644
--- a/src/lib/editor/extensions/pageBreaks.ts
+++ b/src/lib/editor/extensions/pageBreaks.ts
@@ -630,6 +630,19 @@ export const PageBreaks = Extension.create({
                 walkTableRows(child, inTableCell);
                 continue;
               }
+              // The generated table of contents (tableOfContents.ts) is a block atom with
+              // no inner doc positions, so it can't be line-split — measure it atomically
+              // (pushed whole if it overflows; a TOC taller than a page can't be pushed).
+              if (child.dataset?.toc) {
+                leaves.push({
+                  el: child,
+                  kind: 'atomic',
+                  naturalTop: topWithin(child) - cumulativeSpacerHeight,
+                  naturalHeight: child.offsetHeight,
+                  inTableCell,
+                });
+                continue;
+              }
               // A paragraph holding a floated/block image paginates atomically (pushed
               // whole, spacer placed before it): a line-split spacer inside it would sit
               // next to the float, where ProseMirror drops the widget.
diff --git a/src/lib/editor/extensions/tableOfContents.ts b/src/lib/editor/extensions/tableOfContents.ts
new file mode 100644
index 0000000..a527a33
--- /dev/null
+++ b/src/lib/editor/extensions/tableOfContents.ts
@@ -0,0 +1,228 @@
+import { Node, mergeAttributes } from '@tiptap/core';
+import type { Editor } from '@tiptap/core';
+import type { Node as PMNode } from '@tiptap/pm/model';
+
+// A generated table of contents: a block atom listing every heading (levels 1–3) with its
+// live page number. The node view regenerates entries from the headings + pagination and
+// caches them in `entries` (persisted like a Word/LO TOC field); round-trips to ODF/DOCX.
+
+export type TocEntry = { text: string; level: number; page: number };
+
+// Mirrors pageBreaks.ts PAGE_GAP + Editor.svelte getCycle(): the rendered page of a
+// heading is its offsetTop within .tiptap (spacers included) divided by the cycle.
+const PAGE_GAP = 20;
+const FALLBACK_PAGE_HEIGHT = 1123;
+const TITLE = 'Table of Contents';
+
+declare module '@tiptap/core' {
+  interface Commands<ReturnType> {
+    tableOfContents: {
+      setTableOfContents: () => ReturnType;
+    };
+  }
+}
+
+export const TableOfContents = Node.create({
+  name: 'tableOfContents',
+  group: 'block',
+  atom: true,
+  selectable: true,
+  draggable: false,
+
+  addAttributes() {
+    return {
+      entries: {
+        default: [] as TocEntry[],
+        parseHTML: el => {
+          try { return JSON.parse((el as HTMLElement).getAttribute('data-entries') ?? '[]'); }
+          catch { return []; }
+        },
+        renderHTML: attrs => ({ 'data-entries': JSON.stringify(attrs.entries ?? []) }),
+      },
+    };
+  },
+
+  parseHTML() {
+    return [{ tag: 'div[data-toc]' }];
+  },
+
+  renderHTML({ HTMLAttributes }) {
+    return ['div', mergeAttributes(HTMLAttributes, { 'data-toc': 'true' }), TITLE];
+  },
+
+  addCommands() {
+    return {
+      setTableOfContents:
+        () =>
+        ({ commands }) =>
+          commands.insertContent({ type: this.name }),
+    };
+  },
+
+  addNodeView() {
+    return ({ editor, getPos }) => new TocView(editor, getPos as () => number);
+  },
+});
+
+type HeadingRef = { text: string; level: number; pos: number };
+
+// Node view: renders the title + one clickable row per heading. Recomputes on each
+// pagination settle (pm-pagecount, caught on the .paper ancestor) and on doc change,
+// writing entries back to the node attr — guarded by a serialized key against a loop.
+class TocView {
+  dom: HTMLElement;
+  private editor: Editor;
+  private getPos: () => number;
+  private scheduled = false;
+  private lastKey = '';
+  private paper: HTMLElement | null = null;
+  private onPageCount = () => this.schedule();
+
+  constructor(editor: Editor, getPos: () => number) {
+    this.editor = editor;
+    this.getPos = getPos;
+
+    this.dom = document.createElement('div');
+    this.dom.className = 'toc';
+    this.dom.dataset.toc = 'true';
+    this.dom.setAttribute('contenteditable', 'false');
+
+    // Mount deferred so .paper exists and the first pagination pass has run.
+    requestAnimationFrame(() => {
+      this.paper = this.dom.closest('.paper') as HTMLElement | null;
+      this.paper?.addEventListener('pm-pagecount', this.onPageCount);
+      this.render();
+    });
+  }
+
+  private schedule(): void {
+    if (this.scheduled) return;
+    this.scheduled = true;
+    requestAnimationFrame(() => {
+      this.scheduled = false;
+      this.render();
+    });
+  }
+
+  // Every heading (level ≤ 3) with non-empty text, in document order.
+  private headings(): HeadingRef[] {
+    const out: HeadingRef[] = [];
+    this.editor.state.doc.descendants((node, pos) => {
+      if (node.type.name === 'heading') {
+        const text = node.textContent.trim();
+        if (text) out.push({ text, level: Math.min(3, (node.attrs.level as number) ?? 1), pos });
+      }
+    });
+    return out;
+  }
+
+  private cycle(): number {
+    const tiptap = this.editor.view.dom as HTMLElement;
+    const ph = parseFloat(getComputedStyle(tiptap).getPropertyValue('--user-page-height'));
+    return (Number.isFinite(ph) ? ph : FALLBACK_PAGE_HEIGHT) + PAGE_GAP;
+  }
+
+  // Rendered page of a heading: sum offsetTop up the offsetParent chain to .tiptap (the
+  // live DOM already includes pagination spacers, so this is the on-page position),
+  // divided by the page cycle. Mirrors topWithin/getPageForY in pageBreaks.ts.
+  private pageOf(pos: number, cycle: number): number {
+    const tiptap = this.editor.view.dom as HTMLElement;
+    const el = this.editor.view.nodeDOM(pos) as HTMLElement | null;
+    if (!el || el.nodeType !== 1) return 1;
+    let top = 0;
+    let n: HTMLElement | null = el;
+    while (n && n !== tiptap) {
+      top += n.offsetTop;
+      n = n.offsetParent as HTMLElement | null;
+    }
+    return Math.max(1, Math.floor(top / cycle) + 1);
+  }
+
+  private render(): void {
+    if (this.editor.isDestroyed || !this.dom.isConnected) return;
+    const heads = this.headings();
+    const cycle = this.cycle();
+    const entries: TocEntry[] = heads.map(h => ({ text: h.text, level: h.level, page: this.pageOf(h.pos, cycle) }));
+    const key = JSON.stringify(entries);
+    if (key === this.lastKey) return;
+    this.lastKey = key;
+    this.paint(entries, heads);
+    this.syncAttr(entries);
+  }
+
+  private paint(entries: TocEntry[], heads: HeadingRef[]): void {
+    this.dom.textContent = '';
+    const title = document.createElement('div');
+    title.className = 'toc-title';
+    title.textContent = TITLE;
+    this.dom.appendChild(title);
+
+    if (entries.length === 0) {
+      const empty = document.createElement('div');
+      empty.className = 'toc-empty';
+      empty.textContent = 'No headings yet — add an H1/H2/H3 to build the contents.';
+      this.dom.appendChild(empty);
+      return;
+    }
+
+    entries.forEach((e, i) => {
+      const row = document.createElement('div');
+      row.className = `toc-entry toc-level-${e.level}`;
+      const text = document.createElement('span');
+      text.className = 'toc-text';
+      text.textContent = e.text;
+      const leader = document.createElement('span');
+      leader.className = 'toc-leader';
+      const page = document.createElement('span');
+      page.className = 'toc-page';
+      page.textContent = String(e.page);
+      row.append(text, leader, page);
+      const pos = heads[i]?.pos;
+      if (pos != null) {
+        row.addEventListener('mousedown', ev => {
+          ev.preventDefault();
+          ev.stopPropagation();
+          this.goTo(pos);
+        });
+      }
+      this.dom.appendChild(row);
+    });
+  }
+
+  // Scroll the heading into view and drop the cursor into it.
+  private goTo(pos: number): void {
+    const dom = this.editor.view.nodeDOM(pos) as HTMLElement | null;
+    dom?.scrollIntoView({ behavior: 'smooth', block: 'start' });
+    this.editor.chain().focus().setTextSelection(pos + 1).run();
+  }
+
+  private syncAttr(entries: TocEntry[]): void {
+    const pos = this.getPos();
+    if (typeof pos !== 'number') return;
+    const node = this.editor.state.doc.nodeAt(pos);
+    if (!node || node.type.name !== 'tableOfContents') return;
+    if (JSON.stringify(node.attrs.entries ?? []) === JSON.stringify(entries)) return;
+    const tr = this.editor.state.tr.setNodeAttribute(pos, 'entries', entries).setMeta('addToHistory', false);
+    this.editor.view.dispatch(tr);
+  }
+
+  update(node: PMNode): boolean {
+    if (node.type.name !== 'tableOfContents') return false;
+    this.schedule();
+    return true;
+  }
+
+  // Own the mouse on entry rows (navigation) but let clicks on the TOC background reach
+  // ProseMirror so the block can be selected + deleted.
+  stopEvent(event: Event): boolean {
+    return event.type.startsWith('mouse') && !!(event.target as HTMLElement)?.closest?.('.toc-entry');
+  }
+
+  ignoreMutation(): boolean {
+    return true;
+  }
+
+  destroy(): void {
+    this.paper?.removeEventListener('pm-pagecount', this.onPageCount);
+  }
+}
diff --git a/src/lib/export/docx.ts b/src/lib/export/docx.ts
index d3a94cb..8c157c6 100644
--- a/src/lib/export/docx.ts
+++ b/src/lib/export/docx.ts
@@ -1,5 +1,6 @@
 import {
   Document, Packer, Paragraph, TextRun, ImageRun, ExternalHyperlink, Tab,
+  TableOfContents,
   Table, TableRow, TableCell, Header, Footer, PageNumber,
   AlignmentType, HeadingLevel, LevelFormat, UnderlineType, BorderStyle, ShadingType,
   WidthType, HeightRule, PageOrientation, LineRuleType, TableLayoutType,
@@ -329,7 +330,7 @@ function paragraphToDocx(node: TiptapNode, opts: ParaOpts = {}): Paragraph {
 // ---- lists -----------------------------------------------------------------
 function listToParagraphs(
   node: TiptapNode, depth: number, reference: string, extraIndentCm: number,
-  num: Numbering, out: (Paragraph | Table)[],
+  num: Numbering, out: (Paragraph | Table | TableOfContents)[],
 ): void {
   const indentCm = extraIndentCm + (typeof node.attrs?.indent === 'number' ? node.attrs.indent : 0);
   num.ensureLevel(reference, depth, node, indentCm);
@@ -441,8 +442,8 @@ function tableToDocx(node: TiptapNode, contentWidthCm: number, num: Numbering):
 }
 
 // ---- top-level walk --------------------------------------------------------
-function blocksToDocx(content: TiptapNode[], num: Numbering, contentWidthCm: number): (Paragraph | Table)[] {
-  const out: (Paragraph | Table)[] = [];
+function blocksToDocx(content: TiptapNode[], num: Numbering, contentWidthCm: number): (Paragraph | Table | TableOfContents)[] {
+  const out: (Paragraph | Table | TableOfContents)[] = [];
   for (const node of content) {
     if (node.type === 'paragraph' || node.type === 'heading') {
       out.push(paragraphToDocx(node));
@@ -452,6 +453,12 @@ function blocksToDocx(content: TiptapNode[], num: Numbering, contentWidthCm: num
       out.push(tableToDocx(node, contentWidthCm, num));
     } else if (node.type === 'image') {
       out.push(new Paragraph({ children: inlineToRuns([node]) }));
+    } else if (node.type === 'tableOfContents') {
+      // A real, recognized TOC field (levels 1–3, hyperlinked); Word/LibreOffice populate
+      // + link it on field update (features.updateFields does this on open). Title is a
+      // plain bold paragraph so it isn't itself listed; our importer regenerates the node.
+      out.push(new Paragraph({ children: [new TextRun({ text: 'Table of Contents', bold: true, size: 32 })], spacing: { after: cmToTwip(0.3) } }));
+      out.push(new TableOfContents('Table of Contents', { hyperlink: true, headingStyleRange: '1-3' }));
     }
   }
   return out;
@@ -495,6 +502,10 @@ export async function buildDocx(
   const body = blocksToDocx(docJson.content ?? [], num, contentWidthCm);
   if (body.length === 0) body.push(new Paragraph({}));
 
+  // A TOC field is empty until its field is calculated; ask the reader to update fields
+  // on open so Word/LibreOffice populate + hyperlink it (standard for TOC fields).
+  const hasToc = (docJson.content ?? []).some(n => n.type === 'tableOfContents');
+
   const headerPara = hf && !hfIsEmpty(hf.header) ? (hf.header!.content![0] as TiptapNode) : null;
   const footerPara = hf && !hfIsEmpty(hf.footer) ? (hf.footer!.content![0] as TiptapNode) : null;
   // Word's model: header/footer distance is from the page edge; the body still starts
@@ -505,6 +516,7 @@ export async function buildDocx(
   const doc = new Document({
     creator: 'Web ODF Editor',
     defaultTabStop: cmToTwip(1.25),
+    ...(hasToc ? { features: { updateFields: true } } : {}),
     styles: buildStyles(language),
     numbering: { config: num.config },
     sections: [{
diff --git a/src/lib/export/odt.ts b/src/lib/export/odt.ts
index f14611f..ea72d85 100644
--- a/src/lib/export/odt.ts
+++ b/src/lib/export/odt.ts
@@ -64,6 +64,11 @@ const IMG = '';
 // fo:break-before="page" paragraph style for it, and strips the sentinel. U+E005.
 const PGB = '';
 
+// Sentinel wrapping a table-of-contents index (TOC{i}TOC), emitted as a marker
+// paragraph's run text by replaceTableOfContents so it rides odf-kit's paragraph path;
+// applyToc rewrites the whole marker <text:p> to a <text:table-of-content>. U+E006.
+const TOC_SENT = '';
+
 const EXT_BY_MIME: Record<string, string> = {
   'image/png': 'png',
   'image/jpeg': 'jpg',
@@ -241,6 +246,36 @@ function replaceImages(node: TiptapNode, images: ImageExport[]): TiptapNode {
   return { ...node, content };
 }
 
+// One generated table of contents, collected by replaceTableOfContents and emitted by
+// applyToc. Entries are the cached heading→page rows (the node view keeps them current).
+type TocEntry = { text: string; level: number; page: number };
+type TocExport = { entries: TocEntry[] };
+
+// Swap each top-level tableOfContents node for a marker paragraph carrying the TOC
+// sentinel and collect its cached entries. Top-level only (like replacePageBreaks): a
+// sentinel in a cell/list paragraph would corrupt the SEG-based cell rebuild.
+function replaceTableOfContents(doc: TiptapNode, tocs: TocExport[]): TiptapNode {
+  if (!doc.content?.length) return doc;
+  const content: TiptapNode[] = [];
+  for (const child of doc.content) {
+    if (child.type === 'tableOfContents') {
+      const raw = Array.isArray(child.attrs?.entries) ? (child.attrs!.entries as TocEntry[]) : [];
+      const entries = raw
+        .filter(e => e && typeof e.text === 'string')
+        .map(e => ({
+          text: String(e.text),
+          level: Math.min(3, Math.max(1, Number(e.level) || 1)),
+          page: Math.max(1, Number(e.page) || 1),
+        }));
+      tocs.push({ entries });
+      content.push({ type: 'paragraph', content: [{ type: 'text', text: `${TOC_SENT}${tocs.length - 1}${TOC_SENT}` }] });
+      continue;
+    }
+    content.push(child);
+  }
+  return { ...doc, content };
+}
+
 function escapeXml(s: string): string {
   return s.replace(/&/g, '&amp;').replace(/</g, '&lt;').replace(/>/g, '&gt;').replace(/"/g, '&quot;');
 }
@@ -1259,6 +1294,96 @@ function applyImages(odtBytes: Uint8Array, images: ImageExport[]): Uint8Array {
   return rezipOdt(files);
 }
 
+// Minted automatic paragraph style for a TOC entry level: per-level left indent and a
+// right tab stop at the text width with a dotted leader (so the page number right-aligns
+// with dots, matching the on-screen TOC and Word/LibreOffice).
+function contentsEntryStyle(name: string, level: number, tabPosCm: number): string {
+  const indentCm = level === 2 ? 0.6 : level === 3 ? 1.2 : 0;
+  const margin = indentCm > 0 ? ` fo:margin-left="${indentCm}cm"` : '';
+  return (
+    `<style:style style:name="${name}" style:family="paragraph" style:parent-style-name="Standard">` +
+    `<style:paragraph-properties${margin}>` +
+    `<style:tab-stops><style:tab-stop style:position="${tabPosCm}cm" style:type="right" style:leader-style="dotted" style:leader-text="."/></style:tab-stops>` +
+    `</style:paragraph-properties></style:style>`
+  );
+}
+
+// The TOC title style (bold, 16pt) — mirrors the .toc-title on screen.
+function contentsHeadingStyle(): string {
+  return (
+    `<style:style style:name="Contents_20_Heading" style:family="paragraph" style:parent-style-name="Standard">` +
+    `<style:paragraph-properties fo:margin-top="0cm" fo:margin-bottom="0.212cm"/>` +
+    `<style:text-properties fo:font-size="16pt" fo:font-weight="bold"/></style:style>`
+  );
+}
+
+// The full <text:table-of-content>: a source (title + per-level entry templates that
+// carry a right tab stop, page number, and link markers so LibreOffice rebuilds it as a
+// linking TOC) plus a cached index-body (title + one entry paragraph per heading).
+function tocXml(toc: TocExport, index: number): string {
+  const title = 'Table of Contents';
+  const name = `${title}${index + 1}`;
+  const source =
+    `<text:table-of-content-source text:outline-level="3" text:use-index-marks="false" text:use-index-source-styles="false">` +
+    `<text:index-title-template text:style-name="Contents_20_Heading">${escapeXml(title)}</text:index-title-template>` +
+    [1, 2, 3]
+      .map(
+        l =>
+          `<text:table-of-content-entry-template text:outline-level="${l}" text:style-name="Contents_20_${l}">` +
+          `<text:index-entry-link-start/>` +
+          `<text:index-entry-text/>` +
+          `<text:index-entry-tab-stop style:type="right" style:leader-char="."/>` +
+          `<text:index-entry-page-number/>` +
+          `<text:index-entry-link-end/>` +
+          `</text:table-of-content-entry-template>`,
+      )
+      .join('') +
+    `</text:table-of-content-source>`;
+  const body =
+    `<text:index-body>` +
+    `<text:index-title text:name="${escapeXml(name)}_Head">` +
+    `<text:p text:style-name="Contents_20_Heading">${escapeXml(title)}</text:p>` +
+    `</text:index-title>` +
+    toc.entries
+      .map(e => `<text:p text:style-name="Contents_20_${e.level}">${escapeXml(e.text)}<text:tab/>${e.page}</text:p>`)
+      .join('') +
+    `</text:index-body>`;
+  return `<text:table-of-content text:name="${escapeXml(name)}" text:protected="true">${source}${body}</text:table-of-content>`;
+}
+
+// Resolve TOC sentinels: rewrite each marker <text:p>TOC{i}TOC</text:p> to its
+// <text:table-of-content> and mint the Contents_20_* paragraph styles it references.
+function applyToc(odtBytes: Uint8Array, tocs: TocExport[], contentWidthCm: number): Uint8Array {
+  if (!tocs.length) return odtBytes;
+  const files = unzipSync(odtBytes);
+  const contentBytes = files['content.xml'];
+  if (!contentBytes) return odtBytes;
+
+  let content = strFromU8(contentBytes);
+  if (!content.includes(TOC_SENT)) return odtBytes;
+
+  content = content.replace(
+    new RegExp(`<text:p\\b[^>]*>${TOC_SENT}(\\d+)${TOC_SENT}</text:p>`, 'g'),
+    (_m, idx: string) => {
+      const toc = tocs[Number(idx)];
+      return toc ? tocXml(toc, Number(idx)) : '';
+    },
+  );
+  // Defensive: strip any sentinels not consumed above.
+  content = content.split(TOC_SENT).join('');
+
+  const tabPosCm = Math.max(1, Math.round(contentWidthCm * 1000) / 1000);
+  const styles =
+    contentsHeadingStyle() +
+    contentsEntryStyle('Contents_20_1', 1, tabPosCm) +
+    contentsEntryStyle('Contents_20_2', 2, tabPosCm) +
+    contentsEntryStyle('Contents_20_3', 3, tabPosCm);
+  content = injectAutomaticStyles(content, styles);
+
+  files['content.xml'] = strToU8(content);
+  return rezipOdt(files);
+}
+
 // Header/footer input for the export: one single-paragraph doc per zone (or null),
 // the page count snapshot for the stored <text:page-count> value, and the page-edge
 // distances (cm; default HF_DISTANCE_CM) for header (from top) / footer (from bottom).
@@ -1275,7 +1400,8 @@ export async function buildOdt(docJson: TiptapNode, margins: PageMargins = DEFAU
   // Collect embedded images and swap them for IMG sentinels before serialization;
   // applyImages resolves the sentinels and writes the Pictures/ + manifest entries.
   const images: ImageExport[] = [];
-  const raw = replaceImages(replaceTabs(replaceHardBreaks(replacePageBreaks(docJson))), images);
+  const tocs: TocExport[] = [];
+  const raw = replaceImages(replaceTabs(replaceHardBreaks(replacePageBreaks(replaceTableOfContents(docJson, tocs)))), images);
   const headerPara = hf && !hfIsEmpty(hf.header) ? (hf.header!.content![0] as TiptapNode) : null;
   const footerPara = hf && !hfIsEmpty(hf.footer) ? (hf.footer!.content![0] as TiptapNode) : null;
   // Distance from the page edge to the header (top) / footer (bottom). Becomes the
@@ -1387,7 +1513,8 @@ export async function buildOdt(docJson: TiptapNode, margins: PageMargins = DEFAU
   const cleaned = collapseRunWhitespace(styledRows);
   const withBreaks = applyInlineSentinels(cleaned);
   const withImages = applyImages(withBreaks, images);
-  const withPageBreaks = applyPageBreaks(withImages);
+  const withToc = applyToc(withImages, tocs, contentWidthCm);
+  const withPageBreaks = applyPageBreaks(withToc);
   const withStyles = rewriteStylesXml(withPageBreaks, language ?? null);
   return applyHfPostProcess(withStyles, margins, headerPara, footerPara, headerDist, footerDist);
 }
diff --git a/src/lib/import/docx.ts b/src/lib/import/docx.ts
index 307be45..3ab1a94 100644
--- a/src/lib/import/docx.ts
+++ b/src/lib/import/docx.ts
@@ -146,9 +146,52 @@ function documentLanguage(stylesDoc: Document | null, warnings: Set<string>): Do
 }
 
 // ---- block conversion (paragraphs, lists, tables) --------------------------
+// A Word/LibreOffice TOC is a `TOC` field spanning several paragraphs (begin+instrText
+// first, cached entries between, end last), each entry itself a nested PAGEREF field — so
+// field depth is tracked (across one convertBlocks call) to match the TOC's own end.
+type TocFieldState = { fieldDepth: number; tocDepth: number; instr: string[] };
+
+function scanTocField(p: Element, st: TocFieldState): { emit: boolean } {
+  let emit = false;
+  for (const r of Array.from(p.getElementsByTagNameNS(W, 'r'))) {
+    for (const c of Array.from(r.children)) {
+      if (c.namespaceURI !== W) continue;
+      if (c.localName === 'fldChar') {
+        const t = c.getAttributeNS(W, 'fldCharType');
+        if (t === 'begin') { st.fieldDepth++; st.instr[st.fieldDepth] = ''; }
+        else if (t === 'end') {
+          if (st.tocDepth === st.fieldDepth) st.tocDepth = -1;
+          st.instr[st.fieldDepth] = '';
+          st.fieldDepth = Math.max(0, st.fieldDepth - 1);
+        }
+      } else if (c.localName === 'instrText' && st.fieldDepth > 0) {
+        st.instr[st.fieldDepth] += c.textContent ?? '';
+        if (st.tocDepth < 0 && /\bTOC\b/.test(st.instr[st.fieldDepth])) {
+          st.tocDepth = st.fieldDepth;
+          emit = true;
+        }
+      }
+    }
+  }
+  return { emit };
+}
+
+// docx-lib (and Word) wrap a TOC in a content control; detect it by its gallery type or
+// a TOC field instruction inside its content.
+function sdtIsToc(sdt: Element): boolean {
+  const gallery = fc(sdt, 'sdtPr')?.getElementsByTagNameNS(W, 'docPartGallery')[0];
+  if (gallery && /table of contents/i.test(gallery.getAttributeNS(W, 'val') ?? '')) return true;
+  const content = fc(sdt, 'sdtContent');
+  if (!content) return false;
+  return Array.from(content.getElementsByTagNameNS(W, 'instrText')).some(i => /\bTOC\b/.test(i.textContent ?? ''));
+}
+
 function convertBlocks(children: Element[], ctx: Ctx, kind: BlockKind, boldByDefault = false): Node[] {
   const out: Node[] = [];
   const stack: { ilvl: number; numId: number; list: Node }[] = [];
+  // Table-of-contents field tracking (see scanTocField). A TOC node is emitted for the
+  // body only; its cached paragraphs are skipped. The node view regenerates entries live.
+  const tocState: TocFieldState = { fieldDepth: 0, tocDepth: -1, instr: [] };
 
   const closeTop = () => {
     const top = stack.pop()!;
@@ -166,6 +209,11 @@ function convertBlocks(children: Element[], ctx: Ctx, kind: BlockKind, boldByDef
   for (const el of children) {
     if (el.namespaceURI !== W) continue;
     if (el.localName === 'p') {
+      // A paragraph owned by a TOC field is skipped; the field emits one node.
+      const startedInToc = tocState.tocDepth >= 0;
+      const { emit } = scanTocField(el, tocState);
+      if (emit && kind === 'body') { flush(); out.push({ type: 'tableOfContents', attrs: { entries: [] } }); }
+      if (startedInToc || emit) continue;
       const num = paragraphNum(el, ctx);
       if (num) {
         const para = convertParagraph(el, ctx, 'list', boldByDefault);
@@ -192,8 +240,14 @@ function convertBlocks(children: Element[], ctx: Ctx, kind: BlockKind, boldByDef
         out.push(...flattenTable(el, ctx));
       }
     } else if (el.localName === 'sdt') {
-      const content = fc(el, 'sdtContent');
-      if (content) { flush(); out.push(...convertBlocks(Array.from(content.children), ctx, kind, boldByDefault)); }
+      flush();
+      if (sdtIsToc(el)) {
+        // A content-control-wrapped TOC → one node (regenerated live); skip its content.
+        if (kind === 'body') out.push({ type: 'tableOfContents', attrs: { entries: [] } });
+      } else {
+        const content = fc(el, 'sdtContent');
+        if (content) out.push(...convertBlocks(Array.from(content.children), ctx, kind, boldByDefault));
+      }
     }
   }
   flush();
diff --git a/src/lib/import/odt.ts b/src/lib/import/odt.ts
index 7aef637..aed8e64 100644
--- a/src/lib/import/odt.ts
+++ b/src/lib/import/odt.ts
@@ -269,8 +269,12 @@ function convertBlocks(elements: Element[], ctx: Ctx, kind: BlockKind, boldByDef
         if (list) out.push(list);
       } else if (el.localName === 'section') {
         out.push(...convertBlocks(Array.from(el.children), ctx, kind, boldByDefault));
+      } else if (el.localName === 'table-of-content' && kind === 'body') {
+        // Generated table of contents → a tableOfContents node (regenerated live).
+        out.push(convertToc(el));
       } else if (/-index$|^table-of-content$|^bibliography$/.test(el.localName)) {
-        // Generated indexes (ToC, …): keep the rendered text from index-body.
+        // Other generated indexes (bibliography, …) or a TOC nested in a cell: keep the
+        // rendered text from index-body.
         const indexBody = el.getElementsByTagNameNS(NS.text, 'index-body')[0];
         if (indexBody) out.push(...convertBlocks(Array.from(indexBody.children), ctx, kind, boldByDefault));
       }
@@ -295,6 +299,44 @@ function convertBlocks(elements: Element[], ctx: Ctx, kind: BlockKind, boldByDef
   return out;
 }
 
+// A <text:table-of-content> → a tableOfContents node. Entries (text + level + page) are
+// parsed from the cached index-body as a starting cache; the node view recomputes page
+// numbers live after mount, so parse fidelity isn't critical.
+function convertToc(el: Element): Node {
+  const indexBody = el.getElementsByTagNameNS(NS.text, 'index-body')[0];
+  const entries: { text: string; level: number; page: number }[] = [];
+  if (indexBody) {
+    for (const p of Array.from(indexBody.children)) {
+      if (p.namespaceURI !== NS.text || p.localName !== 'p') continue; // skip index-title
+      const style = p.getAttributeNS(NS.text, 'style-name') ?? '';
+      const m = /Contents_20_(\d+)/.exec(style);
+      const level = m ? Math.min(3, Math.max(1, parseInt(m[1], 10))) : 1;
+      const { text, page } = tocEntryTextAndPage(p);
+      if (text) entries.push({ text, level, page: Math.max(1, parseInt(page, 10) || 1) });
+    }
+  }
+  return { type: 'tableOfContents', attrs: { entries } };
+}
+
+// Split a TOC entry paragraph around its last <text:tab/>: the text before it is the
+// entry text, the run after it is the page number. Tabs contribute no textContent, so
+// partition the text nodes by their document position relative to the tab element.
+function tocEntryTextAndPage(p: Element): { text: string; page: string } {
+  const FOLLOWING = 0x04; // Node.DOCUMENT_POSITION_FOLLOWING (the DOM Node is shadowed here)
+  const tabs = p.getElementsByTagNameNS(NS.text, 'tab');
+  const lastTab = tabs.length ? tabs[tabs.length - 1] : null;
+  let before = '';
+  let after = '';
+  const walker = p.ownerDocument.createTreeWalker(p, NodeFilter.SHOW_TEXT);
+  let n: ChildNode | null;
+  while ((n = walker.nextNode() as ChildNode | null)) {
+    const txt = n.nodeValue ?? '';
+    if (lastTab && lastTab.compareDocumentPosition(n) & FOLLOWING) after += txt;
+    else before += txt;
+  }
+  return { text: before.trim(), page: after.trim() };
+}
+
 function convertParaLike(el: Element, ctx: Ctx, kind: BlockKind, boldByDefault = false): Node {
   const { resolver } = ctx;
   const styleName = el.getAttributeNS(NS.text, 'style-name');
diff --git a/src/styles/editor.css b/src/styles/editor.css
index e190f62..15f9573 100644
--- a/src/styles/editor.css
+++ b/src/styles/editor.css
@@ -163,6 +163,52 @@
   background: rgba(255, 145, 0, 0.8);
 }
 
+/* Generated table of contents (tableOfContents.ts). A non-editable block listing
+   headings with dot leaders to their live page number; entries are clickable. */
+.paper .tiptap .toc {
+  margin: 0 0 0.5cm;
+  user-select: none;
+  cursor: default;
+}
+.paper .tiptap .toc-title {
+  font-size: 16pt;
+  font-weight: bold;
+  margin-bottom: 0.3cm;
+}
+.paper .tiptap .toc-empty {
+  font-style: italic;
+  opacity: 0.6;
+}
+.paper .tiptap .toc-entry {
+  display: flex;
+  align-items: baseline;
+  cursor: pointer;
+  line-height: 1.5;
+}
+.paper .tiptap .toc-entry:hover .toc-text {
+  text-decoration: underline;
+}
+.paper .tiptap .toc-level-2 { padding-left: 0.6cm; }
+.paper .tiptap .toc-level-3 { padding-left: 1.2cm; }
+.paper .tiptap .toc-text {
+  white-space: nowrap;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  flex: 0 1 auto;
+}
+/* Dotted leader filling the gap; nudged up to sit on the text baseline. */
+.paper .tiptap .toc-leader {
+  flex: 1 1 auto;
+  min-width: 1em;
+  margin: 0 4px;
+  border-bottom: 1px dotted currentColor;
+  transform: translateY(-0.25em);
+}
+.paper .tiptap .toc-page {
+  flex: 0 0 auto;
+  white-space: nowrap;
+}
+
 /* Inline, as-character images (image.ts). The wrapper reserves the rotated bounding
    box; the rotor holds the <img>, resize handles and rotate grip, rotating together. */
 .paper .tiptap .image-node {
diff --git a/tests/docx-roundtrip.test.ts b/tests/docx-roundtrip.test.ts
index cbaf042..d116b04 100644
--- a/tests/docx-roundtrip.test.ts
+++ b/tests/docx-roundtrip.test.ts
@@ -1,5 +1,5 @@
 import { describe, it, expect } from 'vitest';
-import { zipSync, strToU8 } from 'fflate';
+import { zipSync, strToU8, unzipSync, strFromU8 } from 'fflate';
 import { buildDocx } from '../src/lib/export/docx';
 import { importDocx } from '../src/lib/import/docx';
 import { HEADER_SHADE } from '../src/lib/editor/extensions/tableHeaderRow';
@@ -235,3 +235,34 @@ describe('DOCX import detects headings by outline level (non-"HeadingN" style id
     expect(walk(h, 'text')[0].text).toBe('Localised heading');
   });
 });
+
+describe('DOCX table of contents (TOC field) round trip', () => {
+  const tocDoc = {
+    type: 'doc',
+    content: [
+      { type: 'tableOfContents', attrs: { entries: [
+        { text: 'Alpha', level: 1, page: 1 },
+        { text: 'Beta', level: 2, page: 2 },
+      ] } },
+      heading(1, 'Alpha'),
+      para('body of alpha'),
+      heading(2, 'Beta'),
+    ],
+  };
+
+  it('exports a TOC field (updateFields) and re-imports it as a tableOfContents node', async () => {
+    const bytes = await buildDocx(tocDoc as any);
+    const files = unzipSync(bytes);
+    const docXml = strFromU8(files['word/document.xml']);
+    expect(/\bTOC\b/.test(docXml)).toBe(true);
+    const settings = files['word/settings.xml'];
+    expect(settings ? strFromU8(settings).includes('updateFields') : false).toBe(true);
+
+    const res = importDocx(bytes).content as N;
+    const tocs = walk(res, 'tableOfContents');
+    expect(tocs.length).toBe(1);
+    // Headings survive alongside the TOC.
+    const headings = walk(res, 'heading');
+    expect(headings.map(h => walk(h, 'text')[0]?.text)).toEqual(['Alpha', 'Beta']);
+  });
+});
diff --git a/tests/roundtrip.test.ts b/tests/roundtrip.test.ts
index c8f83c4..7b4b355 100644
--- a/tests/roundtrip.test.ts
+++ b/tests/roundtrip.test.ts
@@ -542,3 +542,43 @@ describe('Leg 4: foreign header/footer → importOdt', () => {
       fhf.warnings.some(w => /per-page/i.test(w)), fhf.warnings);
   });
 });
+
+describe('Leg 5: table of contents (text:table-of-content)', () => {
+  const tocDoc: N = {
+    type: 'doc',
+    content: [
+      { type: 'tableOfContents', attrs: { entries: [
+        { text: 'Introduction', level: 1, page: 1 },
+        { text: 'Background & Aims', level: 2, page: 2 },
+        { text: 'Deep Dive', level: 3, page: 3 },
+      ] } },
+      H({ level: 1 }, T('Introduction')),
+      P(null, T('intro text')),
+      H({ level: 2 }, T('Background & Aims')),
+      H({ level: 3 }, T('Deep Dive')),
+    ],
+  };
+
+  it('exports a real <text:table-of-content> and re-imports it as a tableOfContents node', async () => {
+    const bytes = await buildOdt(tocDoc, margins, 'portrait');
+    const content = strFromU8(unzipSync(bytes)['content.xml']);
+    check('emits <text:table-of-content>', content.includes('<text:table-of-content '), content.slice(0, 200));
+    check('source spans outline-level 3', content.includes('text:outline-level="3"'));
+    check('mints Contents_20_1 style', content.includes('style:name="Contents_20_1"'));
+    check('cached entry carries a tab + page', /Contents_20_1">Introduction<text:tab\/>1<\/text:p>/.test(content));
+    check('ampersand in entry text is escaped', content.includes('Background &amp; Aims'));
+    check('no leftover sentinel', !content.includes(''));
+
+    const res = importOdt(bytes);
+    const blocks = res.content.content ?? [];
+    const toc = blocks.find((n: N) => n.type === 'tableOfContents');
+    check('imports a tableOfContents node', !!toc, blocks.map((n: N) => n.type));
+    const entries = toc?.attrs?.entries ?? [];
+    check('3 entries parsed', entries.length === 3, entries);
+    check('entry 1 text/level', entries[0]?.text === 'Introduction' && entries[0]?.level === 1, entries[0]);
+    check('entry 2 text/level (ampersand)', entries[1]?.text === 'Background & Aims' && entries[1]?.level === 2, entries[1]);
+    check('entry 3 level 3', entries[2]?.level === 3, entries[2]);
+    check('headings after the TOC survive',
+      blocks.some((n: N) => n.type === 'heading' && n.content?.[0]?.text === 'Introduction'));
+  });
+});