diff --git a/apps/api/src/data/initialState.ts b/apps/api/src/data/initialState.ts
index 6ce59f7..e3562a7 100644
--- a/apps/api/src/data/initialState.ts
+++ b/apps/api/src/data/initialState.ts
@@ -76,6 +76,8 @@ const initialGameState = (
     achievements:   structuredClone(defaultAchievements),
     adventurers:    structuredClone(defaultAdventurers),
     apotheosis:     { ...initialApotheosis },
+    autoBoss:       false,
+    autoQuest:      false,
     baseClickPower: 1,
     bosses:         structuredClone(defaultBosses),
     companions:     { activeCompanionId: null, unlockedCompanionIds: [] },
diff --git a/apps/web/src/components/game/bossPanel.tsx b/apps/web/src/components/game/bossPanel.tsx
index d3619cc..c324a61 100644
--- a/apps/web/src/components/game/bossPanel.tsx
+++ b/apps/web/src/components/game/bossPanel.tsx
@@ -226,7 +226,14 @@ const computePartyStats = (
  * @returns The JSX element.
  */
 const BossPanel = (): JSX.Element => {
-  const { state, challengeBoss, formatNumber, toggleAutoBoss } = useGame();
+  const {
+    state,
+    challengeBoss,
+    formatNumber,
+    toggleAutoBoss,
+    autoBossLastResult,
+    autoBossError,
+  } = useGame();
   const [ challengingBossId, setChallengingBossId ] = useState<string | null>(
     null,
   );
@@ -346,6 +353,23 @@ const BossPanel = (): JSX.Element => {
         </div>
       </div>
 
+      {autoBossError === null
+        ? null
+        : <p className="auto-boss-error">
+          {"⚠️ Auto-boss stopped: "}
+          {autoBossError}
+        </p>
+      }
+      {autoBossLastResult !== null && autoBossError === null
+        ? <p className="auto-boss-status">
+          {"🤖 Last fight: "}
+          {autoBossLastResult.bossName}
+          {autoBossLastResult.won
+            ? " — ✅ Won"
+            : " — ❌ Lost"}
+        </p>
+        : null}
+
       <ZoneSelector
         activeZoneId={activeZoneId}
         onSelectZone={setActiveZoneId}
diff --git a/apps/web/src/context/gameContext.tsx b/apps/web/src/context/gameContext.tsx
index 54c82ca..0bf3fc3 100644
--- a/apps/web/src/context/gameContext.tsx
+++ b/apps/web/src/context/gameContext.tsx
@@ -545,6 +545,18 @@ interface GameContextValue {
    * Reset all progress to a fresh save state (resolves schema outdated).
    */
   resetProgress: ()=> Promise<void>;
+
+  /**
+   * Last auto-boss fight result — null until the first auto fight completes or
+   * when auto-boss is toggled off.
+   */
+  autoBossLastResult: { bossName: string; won: boolean; at: number } | null;
+
+  /**
+   * Error message set when auto-boss stopped due to a critical failure (null
+   * when no error). Cleared automatically when the player re-enables auto-boss.
+   */
+  autoBossError: string | null;
 }
 
 export interface BattleResult {
@@ -588,6 +600,12 @@ export const GameProvider = ({
   const [ lastSavedAt, setLastSavedAt ] = useState<number | null>(null);
   const [ isSyncing, setIsSyncing ] = useState(false);
   const [ syncError, setSyncError ] = useState<string | null>(null);
+  const [ autoBossLastResult, setAutoBossLastResult ] = useState<{
+    bossName: string;
+    won:      boolean;
+    at:       number;
+  } | null>(null);
+  const [ autoBossError, setAutoBossError ] = useState<string | null>(null);
   const syncErrorTimerReference = useRef<ReturnType<typeof setTimeout> | null>(
     null,
   );
@@ -1059,6 +1077,14 @@ export const GameProvider = ({
           },
         );
 
+        // Quest failure — turn off auto-quest so the player can reassess
+        if (
+          newlyFailedQuestsReference.current.length > 0
+          && next.autoQuest === true
+        ) {
+          next = { ...next, autoQuest: false };
+        }
+
         return next;
       });
 
@@ -1200,14 +1226,32 @@ export const GameProvider = ({
                 if (previous === null) {
                   return previous;
                 }
-                return applyBossResult(previous, bossId, result);
+                const afterBoss = applyBossResult(previous, bossId, result);
+                // Defeat — turn off auto-boss so the player can reassess
+                if (!result.won) {
+                  return { ...afterBoss, autoBoss: false };
+                }
+                return afterBoss;
+              });
+              setAutoBossLastResult({
+                at:       Date.now(),
+                bossName: bossName,
+                won:      result.won,
               });
-              setBattleResult({ bossName, result });
             }).
             catch((error_: unknown) => {
               logError("auto_boss", error_);
-
-              /* Silently ignore — will retry next tick */
+              const message
+                = error_ instanceof Error
+                  ? error_.message
+                  : String(error_);
+              setAutoBossError(message);
+              setState((previous) => {
+                if (previous === null) {
+                  return previous;
+                }
+                return { ...previous, autoBoss: false };
+              });
             }).
             finally(() => {
               isAutoBossingReference.current = false;
@@ -1782,6 +1826,8 @@ export const GameProvider = ({
   }, []);
 
   const toggleAutoBoss = useCallback(() => {
+    setAutoBossError(null);
+    setAutoBossLastResult(null);
     setState((previous) => {
       if (previous === null) {
         return previous;
@@ -1974,6 +2020,8 @@ export const GameProvider = ({
   const contextValue = useMemo<GameContextValue>(() => {
     return {
       apotheosis,
+      autoBossError,
+      autoBossLastResult,
       battleResult,
       buyAdventurer,
       buyEchoUpgrade,
@@ -2040,6 +2088,8 @@ export const GameProvider = ({
     };
   }, [
     apotheosis,
+    autoBossError,
+    autoBossLastResult,
     battleResult,
     completedQuestToasts,
     failedQuestToasts,