diff --git a/apps/server-e2e/src/note_types/pdf.spec.ts b/apps/server-e2e/src/note_types/pdf.spec.ts
new file mode 100644
index 000000000..af3946607
--- /dev/null
+++ b/apps/server-e2e/src/note_types/pdf.spec.ts
@@ -0,0 +1,43 @@
+import { describe } from "node:test";
+
+import test, { BrowserContext, expect, Page } from "@playwright/test";
+
+import App from "../support/app";
+
+describe("PDF sidebar", () => {
+    // test.beforeAll(async ({ page, context }) => await setLayout({ page, context }, false));
+    // test.beforeAll(async ({ page, context }) => await setLayout({ page, context }, true));
+
+    test("Table of contents works", async ({ page, context }) => {
+        const app = new App(page, context);
+        await app.goto();
+        await app.goToNoteInNewTab("Dacia Logan.pdf");
+
+        const toc = app.sidebar.locator(".toc");
+
+        await expect(toc.locator("li")).toHaveCount(48);
+        await expect(toc.locator("li", { hasText: "Logan Van" })).toHaveCount(1);
+
+        const pdfHelper = new PdfHelper(app);
+        await toc.locator("li", { hasText: "Logan Pick-Up" }).click();
+        await pdfHelper.expectPageToBe(13);
+    });
+});
+
+async function setLayout({ page, context}: { page: Page; context: BrowserContext }, newLayout: boolean) {
+    const app = new App(page, context);
+    await app.goto();
+    await app.setOption("newLayout", newLayout ? "true" : "false");
+}
+
+class PdfHelper {
+    private contentFrame: ReturnType<Page["frameLocator"]>;
+
+    constructor(app: App) {
+        this.contentFrame = app.currentNoteSplit.frameLocator("iframe");
+    }
+
+    async expectPageToBe(expectedPageNumber: number) {
+        await expect(this.contentFrame.locator("#pageNumber")).toHaveValue(`${expectedPageNumber}`);
+    }
+}
diff --git a/apps/server/spec/db/document.db b/apps/server/spec/db/document.db
index 06ca20047..c488fb107 100644
Binary files a/apps/server/spec/db/document.db and b/apps/server/spec/db/document.db differ