diff --git a/packages/app/e2e/sidebar-session-links.spec.ts b/packages/app/e2e/sidebar-session-links.spec.ts
new file mode 100644
index 000000000..fab64736e
--- /dev/null
+++ b/packages/app/e2e/sidebar-session-links.spec.ts
@@ -0,0 +1,61 @@
+import { test, expect } from "./fixtures"
+import { modKey, promptSelector } from "./utils"
+
+type Locator = {
+  first: () => Locator
+  getAttribute: (name: string) => Promise<string | null>
+  scrollIntoViewIfNeeded: () => Promise<void>
+  click: () => Promise<void>
+}
+
+type Page = {
+  locator: (selector: string) => Locator
+  keyboard: {
+    press: (key: string) => Promise<void>
+  }
+}
+
+type Fixtures = {
+  page: Page
+  slug: string
+  sdk: {
+    session: {
+      create: (input: { title: string }) => Promise<{ data?: { id?: string } }>
+      delete: (input: { sessionID: string }) => Promise<unknown>
+    }
+  }
+  gotoSession: (sessionID?: string) => Promise<void>
+}
+
+test("sidebar session links navigate to the selected session", async ({ page, slug, sdk, gotoSession }: Fixtures) => {
+  const stamp = Date.now()
+
+  const one = await sdk.session.create({ title: `e2e sidebar nav 1 ${stamp}` }).then((r) => r.data)
+  const two = await sdk.session.create({ title: `e2e sidebar nav 2 ${stamp}` }).then((r) => r.data)
+
+  if (!one?.id) throw new Error("Session create did not return an id")
+  if (!two?.id) throw new Error("Session create did not return an id")
+
+  try {
+    await gotoSession(one.id)
+
+    const main = page.locator("main")
+    const collapsed = ((await main.getAttribute("class")) ?? "").includes("xl:border-l")
+    if (collapsed) {
+      await page.keyboard.press(`${modKey}+B`)
+      await expect(main).not.toHaveClass(/xl:border-l/)
+    }
+
+    const target = page.locator(`[data-session-id="${two.id}"] a`).first()
+    await expect(target).toBeVisible()
+    await target.scrollIntoViewIfNeeded()
+    await target.click()
+
+    await expect(page).toHaveURL(new RegExp(`/${slug}/session/${two.id}(?:\\?|#|$)`))
+    await expect(page.locator(promptSelector)).toBeVisible()
+    await expect(page.locator(`[data-session-id="${two.id}"] a`).first()).toHaveClass(/\bactive\b/)
+  } finally {
+    await sdk.session.delete({ sessionID: one.id }).catch(() => undefined)
+    await sdk.session.delete({ sessionID: two.id }).catch(() => undefined)
+  }
+})