diff --git a/apps/web/src/components/settings/ForkSettings.tsx b/apps/web/src/components/settings/ForkSettings.tsx
index 4bafd25a55390..44a3892a1d3ae 100644
--- a/apps/web/src/components/settings/ForkSettings.tsx
+++ b/apps/web/src/components/settings/ForkSettings.tsx
@@ -251,7 +251,6 @@ function CustomizationsGroup({
 }
 
 type ServerSwitchKey =
-  | "dontAskMode"
   | "autoOrganizeByFolder"
   | "keepThreadTitlesCurrent"
   | "agentBrowserTabLimits"
@@ -548,10 +547,19 @@ function ForkGeneralBehaviorRows() {
   const mixedIdleTimeout = useScopedSettingsMixed(["idleAgentSessionMinutes"]);
   return (
     <SettingsSection title="Agent sessions & background behavior">
-      <ServerSwitchRow
-        settingKey="dontAskMode"
-        searchId="dont-ask-mode"
-        description="While you're away, answer agents' questions with their recommended option and grant their approvals. Turn off when you return to answer them yourself."
+      <SettingsRow
+        serverScoped
+        settingKeys={["dontAskMode"]}
+        {...searchableSetting("dont-ask-mode")}
+        description="Let agents ask you questions and wait for your answers and approvals. Turn off when you step away to answer questions with their recommended option and grant approvals automatically."
+        control={
+          <ScopedSwitch
+            settingKeys={["dontAskMode"]}
+            checked={!settings.dontAskMode}
+            onCheckedChange={(checked) => updateSettings({ dontAskMode: !checked })}
+            aria-label="Ask mode"
+          />
+        }
       />
       {isElectron && !isMacPlatform(navigator.platform) ? (
         <SettingsRow
diff --git a/apps/web/src/components/settings/ForkSettingsSearch.test.ts b/apps/web/src/components/settings/ForkSettingsSearch.test.ts
index e644fba307adb..febe4e444e7a2 100644
--- a/apps/web/src/components/settings/ForkSettingsSearch.test.ts
+++ b/apps/web/src/components/settings/ForkSettingsSearch.test.ts
@@ -18,6 +18,9 @@ describe("fork settings destinations", () => {
     ["thread rows text size", "sidebar-thread-text-size", "/settings/appearance"],
     ["agent rows text size", "sidebar-agent-text-size", "/settings/appearance"],
     ["process rows text size", "sidebar-process-text-size", "/settings/appearance"],
+    ["ask", "dont-ask-mode", "/settings/general"],
+    ["ask mode", "dont-ask-mode", "/settings/general"],
+    ["don't ask", "dont-ask-mode", "/settings/general"],
     ["don't ask mode", "dont-ask-mode", "/settings/general"],
     ["inside project local .worktrees", "storage-worktrees-location", "/settings/storage"],
   ])("finds %s on its settings page", (query, id, to) => {
diff --git a/apps/web/src/components/settings/ForkSettingsSearch.ts b/apps/web/src/components/settings/ForkSettingsSearch.ts
index 308cf24226a45..c2bcea7d45e71 100644
--- a/apps/web/src/components/settings/ForkSettingsSearch.ts
+++ b/apps/web/src/components/settings/ForkSettingsSearch.ts
@@ -3,10 +3,12 @@ import type { SettingsSearchItem } from "./settingsSearch";
 export const FORK_SETTINGS_SEARCH_ITEMS = [
   {
     id: "dont-ask-mode",
-    title: "Don't ask mode",
+    title: "Ask mode",
     to: "/settings/general",
     scope: "environment-defaults",
-    searchTerms: ["fork automatic questions recommended answers approvals away unattended"],
+    searchTerms: [
+      "don't ask dont ask fork automatic questions recommended answers approvals away unattended",
+    ],
   },
   {
     id: "storage-worktrees-location",
diff --git a/apps/web/src/components/settings/UsageLimitRecoverySettings.tsx b/apps/web/src/components/settings/UsageLimitRecoverySettings.tsx
index 06cba45f886f2..13913846910f0 100644
--- a/apps/web/src/components/settings/UsageLimitRecoverySettings.tsx
+++ b/apps/web/src/components/settings/UsageLimitRecoverySettings.tsx
@@ -49,7 +49,7 @@ export function UsageLimitRecoverySettings() {
         serverScoped
         {...searchableSetting("usage-limit-recovery")}
         settingKeys={["usageLimitRecovery"]}
-        description="Choose what happens after a usage limit. Switching moves only the limited thread and continues without asking, including in Don't ask mode. If no alternative is available, it waits for reset."
+        description="Choose what happens after a usage limit. Switching moves only the limited thread and continues without asking, including when Ask mode is off. If no alternative is available, it waits for reset."
         control={
           <Select
             value={settings.usageLimitRecovery}
diff --git a/apps/web/src/components/sidebar/SidebarChrome.tsx b/apps/web/src/components/sidebar/SidebarChrome.tsx
index 7e1ff7a493cb0..f5248b5a1db94 100644
--- a/apps/web/src/components/sidebar/SidebarChrome.tsx
+++ b/apps/web/src/components/sidebar/SidebarChrome.tsx
@@ -2,8 +2,7 @@ import {
   ArrowLeftIcon,
   ChartNoAxesColumnIcon,
   CircleDotIcon,
-  MessageCircleOffIcon,
-  MessageCircleQuestionMarkIcon,
+  MessageCircleQuestionIcon,
   SettingsIcon,
 } from "lucide-react";
 import type { CSSProperties, ReactNode } from "react";
@@ -175,13 +174,15 @@ function SidebarUtilityItem({
   );
 }
 
-/** The primary server's Don't ask mode: while on, it answers every agent question and approval. */
-function SidebarDontAskModeItem() {
+/** Ask mode reflects the inverse of the primary server's automatic-answer setting. */
+function SidebarAskModeItem() {
   const available = usePrimarySettingsAvailable();
-  const on = usePrimarySettings((settings) => settings.dontAskMode);
+  const on = usePrimarySettings((settings) => !settings.dontAskMode);
   const updateSettings = useUpdatePrimarySettings();
   if (!available) return null;
-  const label = on ? "Don't ask mode is on" : "Don't ask mode is off";
+  const label = on
+    ? "Ask mode: on (agents can ask you questions)"
+    : "Ask mode: off (agents decide without asking)";
   return (
     // Last in the footer. The desktop update control before it already pushes right (`ml-auto`), so
     // it drops its own push there instead of splitting the free space with it.
@@ -192,16 +193,16 @@ function SidebarDontAskModeItem() {
             <SidebarMenuButton
               aria-label={label}
               aria-pressed={on}
-              onClick={() => updateSettings({ dontAskMode: !on })}
+              onClick={() => updateSettings({ dontAskMode: on })}
               size="icon"
-              // On: the orange the sidebar uses for the questions and approvals it would answer.
+              // Orange matches the sidebar's questions waiting for you.
               style={
                 on
                   ? ({ "--sidebar-icon-color": "var(--warning-foreground)" } as CSSProperties)
                   : undefined
               }
             >
-              {on ? <MessageCircleOffIcon /> : <MessageCircleQuestionMarkIcon />}
+              <MessageCircleQuestionIcon />
             </SidebarMenuButton>
           }
         />
@@ -210,8 +211,8 @@ function SidebarDontAskModeItem() {
             <span className="font-medium text-foreground">{label}</span>
             <span className="text-muted-foreground">
               {on
-                ? "Agents' questions get their recommended option and approvals are granted. Click when you're back."
-                : "Turn on when you step away: agents' questions get their recommended option and approvals are granted."}
+                ? "Turn off when you step away: questions get their recommended option and approvals are granted."
+                : "Questions get their recommended option and approvals are granted. Turn on to answer them yourself."}
             </span>
           </div>
         </TooltipPopup>
@@ -300,7 +301,7 @@ export const SidebarUtilityMenu = memo(function SidebarUtilityMenu() {
         </>
       )}
       <SidebarUpdatePill />
-      {isOnUtilityPage ? null : <SidebarDontAskModeItem />}
+      {isOnUtilityPage ? null : <SidebarAskModeItem />}
     </SidebarMenu>
   );
 });
diff --git a/docs/user/permission-modes.md b/docs/user/permission-modes.md
index 9c7a4b3b17fc0..97c403ecf58e0 100644
--- a/docs/user/permission-modes.md
+++ b/docs/user/permission-modes.md
@@ -18,19 +18,22 @@ and modes you choose in a draft keep their permissions.
 Approve or reject requests in the conversation to let the agent continue. Permission modes do
 not prevent the agent from asking questions about the task.
 
-## Don't ask mode
-
-Turn on **Don't ask mode** with the speech-bubble switch at the bottom left of the sidebar when you
-step away. While it is on, the server answers for you the moment an agent waits: it approves each
-request once, and answers each question with its first option (the agent's recommendation) plus a
-note asking the agent to list the decisions it made. Switching it on also answers everything
-already waiting in every thread, including delegated ones. Answers it gave are marked **Answered by
-Don't ask mode** or **Approved by Don't ask mode** in the conversation. Switch it off to have agents
-wait for you again.
-
-The switch belongs to your primary environment's server, so it keeps working with no client open
-and stays on after a restart. Requests left waiting across a server restart are handled the way a
-restart normally handles them, not by Don't ask mode. Agents cannot change it.
+## Ask mode
+
+**Ask mode** lets agents wait for your answers and approvals. Toggle it in the sidebar footer or
+in **Settings → General → Ask mode** (also available in **Customizations**). Orange means it is on;
+gray means it is off.
+
+Turn Ask mode off when you step away. While it is off, the server answers for you the moment an
+agent waits: it approves each request once, and answers each question with its first option (the
+agent's recommendation) plus a note asking the agent to list the decisions it made. Turning it off
+also answers everything already waiting in every thread, including delegated ones. Automatic
+answers retain the conversation labels **Answered by Don't ask mode** and **Approved by Don't ask
+mode**. Turn Ask mode on to have agents wait for you again.
+
+The sidebar switch belongs to your primary environment's server, so automatic answers keep working
+with no client open and the setting persists after a restart. Requests left waiting across a
+server restart are handled the way a restart normally handles them. Agents cannot change the setting.
 
 ## Provider differences
 
diff --git a/docs/user/thread-sidebar.md b/docs/user/thread-sidebar.md
index 3a69c5b89d90e..cc13822792ece 100644
--- a/docs/user/thread-sidebar.md
+++ b/docs/user/thread-sidebar.md
@@ -297,7 +297,7 @@ archiving, or settling it prevents a pending continuation from starting.
 - **Wait for reset** snoozes and continues limited threads when the reported allowance returns.
 - **Switch provider** moves the limited thread between Codex and Claude and sends
   “Continue where you left off.” with a context handoff. Other threads and children keep running.
-  Switching proceeds without asking, including in Don't ask mode.
+  Switching proceeds without asking, including when Ask mode is off.
 
 A thread uses its role's available alternatives, ordered by weekly headroom. Implementor threads
 use the profile matching their current model and effort, or the first configured Implementor