diff --git a/apps/client/src/components/note_context.ts b/apps/client/src/components/note_context.ts
index fd33c94ae..c9261f38e 100644
--- a/apps/client/src/components/note_context.ts
+++ b/apps/client/src/components/note_context.ts
@@ -12,6 +12,7 @@ import server from "../services/server.js";
 import treeService from "../services/tree.js";
 import utils from "../services/utils.js";
 import { ReactWrappedWidget } from "../widgets/basic_widget.js";
+import type { HeadingContext } from "../widgets/sidebar/TableOfContents.js";
 import appContext, { type EventData, type EventListener } from "./app_context.js";
 import Component from "./component.js";
 
@@ -22,6 +23,12 @@ export interface SetNoteOpts {
 
 export type GetTextEditorCallback = (editor: CKTextEditor) => void;
 
+export interface NoteContextDataMap {
+    toc: HeadingContext;
+}
+
+type ContextDataKey = keyof NoteContextDataMap;
+
 class NoteContext extends Component implements EventListener<"entitiesReloaded"> {
     ntxId: string | null;
     hoistedNoteId: string;
@@ -469,8 +476,9 @@ class NoteContext extends Component implements EventListener<"entitiesReloaded">
      * @param key - Unique identifier for the data type (e.g., "toc", "pdfPages", "codeOutline")
      * @param value - The data to store (will be cleared when switching notes)
      */
-    setContextData<T>(key: string, value: T): void {
+    setContextData<K extends ContextDataKey>(key: K, value: NoteContextDataMap[K]): void {
         this.contextData.set(key, value);
+        console.trace("Set context data", key, value);
         // Trigger event so subscribers can react
         this.triggerEvent("contextDataChanged", {
             noteContext: this,
@@ -485,21 +493,21 @@ class NoteContext extends Component implements EventListener<"entitiesReloaded">
      * @param key - The data key to retrieve
      * @returns The stored data, or undefined if not found
      */
-    getContextData<T>(key: string): T | undefined {
-        return this.contextData.get(key) as T | undefined;
+    getContextData<K extends ContextDataKey>(key: K): NoteContextDataMap[K] | undefined {
+        return this.contextData.get(key) as NoteContextDataMap[K] | undefined;
     }
 
     /**
      * Check if context data exists for a given key.
      */
-    hasContextData(key: string): boolean {
+    hasContextData(key: ContextDataKey): boolean {
         return this.contextData.has(key);
     }
 
     /**
      * Clear specific context data.
      */
-    clearContextData(key: string): void {
+    clearContextData(key: ContextDataKey): void {
         this.contextData.delete(key);
         this.triggerEvent("contextDataChanged", {
             noteContext: this,
diff --git a/apps/client/src/widgets/sidebar/TableOfContents.tsx b/apps/client/src/widgets/sidebar/TableOfContents.tsx
index 42dc7f781..97bceaab0 100644
--- a/apps/client/src/widgets/sidebar/TableOfContents.tsx
+++ b/apps/client/src/widgets/sidebar/TableOfContents.tsx
@@ -21,6 +21,11 @@ interface HeadingsWithNesting extends RawHeading {
     children: HeadingsWithNesting[];
 }
 
+export interface HeadingContext {
+    // scrollToHeading(heading: RawHeading): void;
+    headings: RawHeading[];
+}
+
 export default function TableOfContents() {
     const { note, noteContext } = useActiveNoteContext();
     const noteType = useNoteProperty(note, "type");
@@ -38,6 +43,7 @@ export default function TableOfContents() {
 
 function PdfTableOfContents() {
     const data = useGetContextData("toc");
+    console.log("Rendering with data", data);
 
     return (
         <pre>{JSON.stringify(data, null, 2)}</pre>
diff --git a/apps/client/src/widgets/type_widgets/file/Pdf.tsx b/apps/client/src/widgets/type_widgets/file/Pdf.tsx
index 7f405b42e..5d68d403f 100644
--- a/apps/client/src/widgets/type_widgets/file/Pdf.tsx
+++ b/apps/client/src/widgets/type_widgets/file/Pdf.tsx
@@ -39,10 +39,13 @@ export default function PdfPreview({ note, blob, componentId, noteContext }: {
 
             if (event.data.type === "pdfjs-viewer-toc") {
                 if (event.data.data) {
-                    noteContext.setContextData("toc", event.data.data);
+                    // Convert PDF outline to HeadingContext format
+                    noteContext.setContextData("toc", {
+                        headings: convertPdfOutlineToHeadings(event.data.data)
+                    });
                 } else {
-                    // No ToC available, fallback to note title
-                    noteContext.setContextData("toc", note.title);
+                    // No ToC available, use empty headings
+                    noteContext.setContextData("toc", { headings: [] });
                 }
             }
         }
@@ -60,8 +63,6 @@ export default function PdfPreview({ note, blob, componentId, noteContext }: {
         }
     }, [ blob ]);
 
-    // Initial ToC is set to note.title, will be replaced by actual ToC when received
-    useSetContextData(noteContext, "toc", note.title);
 
     return (historyConfig &&
         <iframe
@@ -130,3 +131,29 @@ function cssVarsToString(vars) {
         .map(([k, v]) => `  ${k}: ${v};`)
         .join('\n')}\n}`;
 }
+
+interface PdfOutlineItem {
+    title: string;
+    level: number;
+    dest: any;
+    items: PdfOutlineItem[];
+}
+
+function convertPdfOutlineToHeadings(outline: PdfOutlineItem[], parentLevel = 0) {
+    const headings: any[] = [];
+
+    for (const item of outline) {
+        headings.push({
+            level: parentLevel + 1,
+            text: item.title,
+            id: `pdf-outline-${headings.length}`,
+            element: null // PDFs don't have DOM elements
+        });
+
+        if (item.items && item.items.length > 0) {
+            headings.push(...convertPdfOutlineToHeadings(item.items, parentLevel + 1));
+        }
+    }
+
+    return headings;
+}