diff --git a/webui/src/lib/chat-groups.ts b/webui/src/lib/chat-groups.ts
index 2fda9f8f0..f4b4b9a1a 100644
--- a/webui/src/lib/chat-groups.ts
+++ b/webui/src/lib/chat-groups.ts
@@ -281,19 +281,18 @@ function groupSessionsByProject(
     ),
   }));
 
-  groups.sort((a, b) => {
-    const timeOrder = dateToTime(b.updatedAt) - dateToTime(a.updatedAt);
-    if (timeOrder !== 0) return timeOrder;
-    return a.label.localeCompare(b.label, "en", {
-      numeric: true,
-      sensitivity: "base",
-    });
-  });
-
   if (conversations.length) {
+    const chatsUpdatedAt = conversations.reduce<string | null>(
+      (best, s) => {
+        const candidate = s.updatedAt ?? s.createdAt ?? null;
+        return isNewerDate(candidate, best) ? candidate : best;
+      },
+      null,
+    );
     groups.push({
       id: "workspace:chats",
       label: labels.all,
+      updatedAt: chatsUpdatedAt,
       sessions: sortProjectSessions(
         conversations,
         options.sort,
@@ -304,6 +303,15 @@ function groupSessionsByProject(
     });
   }
 
+  groups.sort((a, b) => {
+    const timeOrder = dateToTime(b.updatedAt) - dateToTime(a.updatedAt);
+    if (timeOrder !== 0) return timeOrder;
+    return a.label.localeCompare(b.label, "en", {
+      numeric: true,
+      sensitivity: "base",
+    });
+  });
+
   return groups;
 }
 
diff --git a/webui/src/tests/chat-list.test.tsx b/webui/src/tests/chat-list.test.tsx
index eb3ae5c8b..f678d3c06 100644
--- a/webui/src/tests/chat-list.test.tsx
+++ b/webui/src/tests/chat-list.test.tsx
@@ -256,4 +256,60 @@ describe("ChatList", () => {
     expect(within(chatsSection).getByText("Chat 0")).toBeInTheDocument();
     expect(within(chatsSection).getByRole("button", { name: "Show less" })).toBeInTheDocument();
   });
+
+  it("sorts Chats section among project groups by recency, not always last", () => {
+    const sessions = [
+      session({
+        chatId: "recent-chat",
+        title: "Recent chat",
+        updatedAt: "2026-05-21T12:00:00Z",
+      }),
+      session({
+        chatId: "project-a",
+        title: "Project A task",
+        updatedAt: "2026-05-21T10:00:00Z",
+        workspaceScope: {
+          project_path: "/Users/me/project-a",
+          project_name: "project-a",
+          access_mode: "restricted",
+        },
+      }),
+      session({
+        chatId: "project-b",
+        title: "Project B task",
+        updatedAt: "2026-05-21T11:00:00Z",
+        workspaceScope: {
+          project_path: "/Users/me/project-b",
+          project_name: "project-b",
+          access_mode: "restricted",
+        },
+      }),
+    ];
+
+    render(
+      <ChatList
+        sessions={sessions}
+        activeKey="websocket:recent-chat"
+        onSelect={vi.fn()}
+        onRequestDelete={vi.fn()}
+        onTogglePin={vi.fn()}
+        onRequestRename={vi.fn()}
+        onToggleArchive={vi.fn()}
+        showTimestamps
+      />,
+    );
+
+    const allRegions = screen.getAllByRole("region");
+    const regionNames = allRegions.map((r) => r.getAttribute("aria-label") ?? r.textContent);
+
+    // The most recently updated conversation ("Recent chat" at 12:00) must be
+    // in the first group — Chats should come before both projects.
+    const chatsIdx = regionNames.findIndex((n) => n?.includes("Chats"));
+    const projAIdx = regionNames.findIndex((n) => n?.includes("project-a"));
+    const projBIdx = regionNames.findIndex((n) => n?.includes("project-b"));
+
+    expect(chatsIdx).toBeLessThan(projAIdx);
+    expect(chatsIdx).toBeLessThan(projBIdx);
+    expect(within(allRegions[chatsIdx]).getByText("Recent chat")).toBeInTheDocument();
+  });
 });