diff --git a/apps/web/components/app-sidebar/app-sidebar-footer.test.tsx b/apps/web/components/app-sidebar/app-sidebar-footer.test.tsx
index dc22b26cc0..fc574dc4aa 100644
--- a/apps/web/components/app-sidebar/app-sidebar-footer.test.tsx
+++ b/apps/web/components/app-sidebar/app-sidebar-footer.test.tsx
@@ -17,7 +17,6 @@ const state = {
     ],
   },
   appSidebar: { settingsMode: false },
-  toggleAppSidebarSettingsMode: mocks.toggleSettingsMode,
 };
 
 let officeEnabled = false;
@@ -64,7 +63,7 @@ import { AppSidebarFooter } from "./app-sidebar-footer";
 function renderFooter() {
   return render(
     <TooltipProvider>
-      <AppSidebarFooter collapsed={false} />
+      <AppSidebarFooter collapsed={false} onToggleSettingsMode={mocks.toggleSettingsMode} />
     </TooltipProvider>,
   );
 }
diff --git a/apps/web/components/app-sidebar/app-sidebar-footer.tsx b/apps/web/components/app-sidebar/app-sidebar-footer.tsx
index 1df28655b5..8e5b67a83d 100644
--- a/apps/web/components/app-sidebar/app-sidebar-footer.tsx
+++ b/apps/web/components/app-sidebar/app-sidebar-footer.tsx
@@ -32,6 +32,7 @@ import {
 
 type AppSidebarFooterProps = {
   collapsed: boolean;
+  onToggleSettingsMode: () => void;
 };
 
 type FooterIconButtonProps = {
@@ -95,7 +96,7 @@ function FooterIconButton({
   );
 }
 
-export function AppSidebarFooter({ collapsed }: AppSidebarFooterProps) {
+export function AppSidebarFooter({ collapsed, onToggleSettingsMode }: AppSidebarFooterProps) {
   const router = useRouter();
   const workspaces = useAppStore((s) => s.workspaces);
   const workspaceId = workspaces.activeId;
@@ -105,7 +106,6 @@ export function AppSidebarFooter({ collapsed }: AppSidebarFooterProps) {
     ? resolveLastKanbanWorkspace(workspaces.items)
     : resolveLastOfficeWorkspace(workspaces.items);
   const settingsMode = useAppStore((s) => s.appSidebar.settingsMode);
-  const toggleSettingsMode = useAppStore((s) => s.toggleAppSidebarSettingsMode);
   const officeEnabled = useFeature("office");
   const releaseNotes = useReleaseNotes();
   const [improveOpen, setImproveOpen] = useState(false);
@@ -121,7 +121,7 @@ export function AppSidebarFooter({ collapsed }: AppSidebarFooterProps) {
         icon={IconSettings}
         label={settingsMode ? "Close settings" : "Settings"}
         collapsed={collapsed}
-        onClick={toggleSettingsMode}
+        onClick={onToggleSettingsMode}
         active={settingsMode}
         testId="sidebar-settings-gear"
       />
diff --git a/apps/web/components/app-sidebar/app-sidebar.tsx b/apps/web/components/app-sidebar/app-sidebar.tsx
index 655b263f1e..2355b92f9e 100644
--- a/apps/web/components/app-sidebar/app-sidebar.tsx
+++ b/apps/web/components/app-sidebar/app-sidebar.tsx
@@ -103,6 +103,7 @@ export function AppSidebar() {
   const storedWidth = useAppStore((s) => s.appSidebar.width);
   const toggleSection = useAppStore((s) => s.toggleAppSidebarSection);
   const toggleCollapsed = useAppStore((s) => s.toggleAppSidebar);
+  const toggleSettingsMode = useAppStore((s) => s.toggleAppSidebarSettingsMode);
   const setSettingsMode = useAppStore((s) => s.setAppSidebarSettingsMode);
   const setWidth = useAppStore((s) => s.setAppSidebarWidth);
   const pathname = usePathname();
@@ -140,6 +141,14 @@ export function AppSidebar() {
   );
 
   const expandedWidth = Math.max(APP_SIDEBAR_EXPANDED_WIDTH, storedWidth);
+  const settingsModeTogglePathnameRef = useRef<string | null>(null);
+
+  const handleToggleSettingsMode = useCallback(() => {
+    // History updates before React renders the new pathname; remember which
+    // route the user actually clicked on so delayed route sync cannot undo it.
+    settingsModeTogglePathnameRef.current = window.location.pathname;
+    toggleSettingsMode();
+  }, [toggleSettingsMode]);
 
   // Keep the transient settings takeover aligned with route ownership. It is
   // intentionally not persisted, so direct reloads on `/settings/...` need to
@@ -150,10 +159,11 @@ export function AppSidebar() {
     if (!pathname || prevPathnameRef.current === pathname) return;
     prevPathnameRef.current = pathname;
     if (isSettingsRoute(pathname)) {
+      settingsModeTogglePathnameRef.current = null;
       if (!settingsMode) setSettingsMode(true);
       return;
     }
-    if (settingsMode) {
+    if (settingsMode && settingsModeTogglePathnameRef.current !== pathname) {
       setSettingsMode(false);
     }
   }, [pathname, settingsMode, setSettingsMode]);
@@ -192,7 +202,7 @@ export function AppSidebar() {
     >
       <AppSidebarHeader collapsed={collapsed} onToggleCollapse={toggleCollapsed} />
       <AppSidebarNavigation collapsed={collapsed} inOffice={inOffice} settingsMode={settingsMode} />
-      <AppSidebarFooter collapsed={collapsed} />
+      <AppSidebarFooter collapsed={collapsed} onToggleSettingsMode={handleToggleSettingsMode} />
       {!collapsed && <AppSidebarResizeHandle onMouseDown={handleResize} />}
     </aside>
   );
diff --git a/apps/web/e2e/tests/settings/settings-gear-only.spec.ts b/apps/web/e2e/tests/settings/settings-gear-only.spec.ts
index 91c83605aa..a95eb58519 100644
--- a/apps/web/e2e/tests/settings/settings-gear-only.spec.ts
+++ b/apps/web/e2e/tests/settings/settings-gear-only.spec.ts
@@ -72,4 +72,23 @@ test.describe("Settings sidebar takeover", () => {
     await expect(sidebar).toHaveAttribute("data-collapsed", "false");
     await expect(takeover).toBeVisible();
   });
+
+  test("a route change cannot undo the first gear click", async ({ testPage }) => {
+    await testPage.goto("/");
+
+    const takeover = testPage.getByTestId("app-sidebar-settings-mode");
+    await expect(testPage.getByTestId("sidebar-settings-gear")).toBeVisible();
+
+    // Keep both actions in one browser task so the route-sync effect is still
+    // pending when the user action arrives. The click must win.
+    await testPage.evaluate(() => {
+      window.history.pushState({}, "", "/tasks");
+      window.dispatchEvent(new Event("kandev:navigation"));
+      const gear = document.querySelector<HTMLElement>('[data-testid="sidebar-settings-gear"]');
+      if (!gear) throw new Error("sidebar-settings-gear not found");
+      gear.click();
+    });
+
+    await expect(takeover).toBeVisible();
+  });
 });