diff --git a/packages/app/src/pages/layout.tsx b/packages/app/src/pages/layout.tsx
index 473555880..8ebc415b4 100644
--- a/packages/app/src/pages/layout.tsx
+++ b/packages/app/src/pages/layout.tsx
@@ -79,6 +79,7 @@ import {
 } from "./layout/deep-links"
 import { createInlineEditorController } from "./layout/inline-editor"
 import {
+  buildPawworkSidebarSessionRows,
   pawworkSessionDirectories,
   sortPawworkSidebarSessions,
 } from "./layout/pawwork-session-source"
@@ -573,12 +574,14 @@ export default function Layout(props: ParentProps) {
   )
 
   const pawworkSessions = createMemo(() => {
-    const rows = pawworkSessionWindow().sessions.map((session) => ({
-      session,
-      slug: base64Encode(session.directory),
-      projectLabel: projectLabelForSession(session),
-      created: session.time.created,
-    }))
+    const rows = buildPawworkSidebarSessionRows(pawworkSessionWindow().sessions, {
+      slugForDirectory: base64Encode,
+      projectLabelForSession,
+      messagesForSession: (session) => {
+        const [store] = globalSync.child(session.directory, { bootstrap: false, pin: false })
+        return store.message[session.id]
+      },
+    })
     return sortPawworkSidebarSessions(rows.map((item) => ({ ...item, id: item.session.id }))).map(({ id: _, ...item }) => item)
   })
 
diff --git a/packages/app/src/pages/layout/pawwork-session-source.test.ts b/packages/app/src/pages/layout/pawwork-session-source.test.ts
index 141b7114b..714e69dc4 100644
--- a/packages/app/src/pages/layout/pawwork-session-source.test.ts
+++ b/packages/app/src/pages/layout/pawwork-session-source.test.ts
@@ -1,5 +1,6 @@
 import { describe, expect, test } from "bun:test"
 import {
+  buildPawworkSidebarSessionRows,
   pawworkSidebarSessionTime,
   resolvePawworkProjectLabels,
   sortPawworkSidebarSessions,
@@ -130,6 +131,59 @@ describe("sortPawworkSidebarSessions", () => {
   })
 })
 
+describe("buildPawworkSidebarSessionRows", () => {
+  test("uses loaded user message time for sidebar rows", () => {
+    const result = buildPawworkSidebarSessionRows(
+      [
+        {
+          id: "session-old",
+          directory: "/repo",
+          time: { created: 100, updated: 900 },
+        },
+      ],
+      {
+        slugForDirectory: (directory) => `slug:${directory}`,
+        projectLabelForSession: () => "PawWork",
+        messagesForSession: () => [
+          { id: "msg_1", role: "assistant", time: { created: 950 } },
+          { id: "msg_2", role: "user", time: { created: 800 } },
+        ],
+      },
+    )
+
+    expect(result).toEqual([
+      {
+        session: {
+          id: "session-old",
+          directory: "/repo",
+          time: { created: 100, updated: 900 },
+        },
+        slug: "slug:/repo",
+        projectLabel: "PawWork",
+        created: 800,
+      },
+    ])
+  })
+
+  test("falls back to session creation time when messages are missing", () => {
+    const result = buildPawworkSidebarSessionRows(
+      [
+        {
+          id: "session-without-cache",
+          directory: "/repo",
+          time: { created: 300, updated: 900 },
+        },
+      ],
+      {
+        slugForDirectory: (directory) => `slug:${directory}`,
+        projectLabelForSession: () => "PawWork",
+      },
+    )
+
+    expect(result[0].created).toBe(300)
+  })
+})
+
 describe("pawworkSidebarSessionTime", () => {
   test("uses the latest loaded user message time", () => {
     expect(
diff --git a/packages/app/src/pages/layout/pawwork-session-source.ts b/packages/app/src/pages/layout/pawwork-session-source.ts
index 8d19ff77e..df863e883 100644
--- a/packages/app/src/pages/layout/pawwork-session-source.ts
+++ b/packages/app/src/pages/layout/pawwork-session-source.ts
@@ -29,6 +29,11 @@ type MessageTimeLike = {
   }
 }
 
+type SidebarRowSessionLike = SessionTimeLike & {
+  id: string
+  directory: string
+}
+
 const isFiniteNumber = (value: unknown): value is number => typeof value === "number" && Number.isFinite(value)
 
 const shortenHome = (value: string, home?: string) => {
@@ -74,6 +79,22 @@ export function pawworkSidebarSessionTime(session: SessionTimeLike, messages?: M
   return isFiniteNumber(sessionCreated) ? sessionCreated : 0
 }
 
+export function buildPawworkSidebarSessionRows<T extends SidebarRowSessionLike>(
+  sessions: T[],
+  input: {
+    slugForDirectory: (directory: string) => string
+    projectLabelForSession: (session: T) => string
+    messagesForSession?: (session: T) => MessageTimeLike[] | undefined
+  },
+) {
+  return sessions.map((session) => ({
+    session,
+    slug: input.slugForDirectory(session.directory),
+    projectLabel: input.projectLabelForSession(session),
+    created: pawworkSidebarSessionTime(session, input.messagesForSession?.(session)),
+  }))
+}
+
 export function pawworkSessionDirectories(input: {
   project: LocalProject | undefined
   activeProjectWorktree?: string