diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index a53df80e474d..5bd04d03962a 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -17,10 +17,10 @@ import { AlertType, useAlerts } from './alerts';
 import { useConfig } from './ConfigContext';
 import { useModelAndProvider } from './ModelAndProviderContext';
 import { useWhisper } from '../hooks/useWhisper';
+import { DICTATION_PROVIDER_ELEVENLABS } from '../hooks/dictationConstants';
 import { WaveformVisualizer } from './WaveformVisualizer';
 import { toastError } from '../toasts';
 import MentionPopover, { DisplayItemWithMatch } from './MentionPopover';
-import { useDictationSettings } from '../hooks/useDictationSettings';
 import { COST_TRACKING_ENABLED, VOICE_DICTATION_ELEVENLABS_ENABLED } from '../updates';
 import { CostTracker } from './bottom_menu/CostTracker';
 import { DroppedFile, useFileDrop } from '../hooks/useFileDrop';
@@ -265,6 +265,7 @@ export default function ChatInput({
     stopRecording,
     recordingDuration,
     estimatedSize,
+    dictationSettings,
   } = useWhisper({
     onTranscription: (text) => {
       trackVoiceDictation('transcribed');
@@ -289,8 +290,6 @@ export default function ChatInput({
       });
     },
   });
-
-  const { settings: dictationSettings } = useDictationSettings();
   const internalTextAreaRef = useRef<HTMLTextAreaElement>(null);
   const textAreaRef = inputRef || internalTextAreaRef;
   const timeoutRefsRef = useRef<Set<ReturnType<typeof setTimeout>>>(new Set());
@@ -618,17 +617,20 @@ export default function ChatInput({
     return [...pastedImageData, ...droppedImageData];
   }, [pastedImages, allDroppedFiles]);
 
-  const appendDroppedFilePaths = useCallback((text: string): string => {
-    const droppedFilePaths = allDroppedFiles
-      .filter((file) => !file.isImage && !file.error && !file.isLoading)
-      .map((file) => file.path);
+  const appendDroppedFilePaths = useCallback(
+    (text: string): string => {
+      const droppedFilePaths = allDroppedFiles
+        .filter((file) => !file.isImage && !file.error && !file.isLoading)
+        .map((file) => file.path);
 
-    if (droppedFilePaths.length > 0) {
-      const pathsString = droppedFilePaths.join(' ');
-      return text ? `${text} ${pathsString}` : pathsString;
-    }
-    return text;
-  }, [allDroppedFiles]);
+      if (droppedFilePaths.length > 0) {
+        const pathsString = droppedFilePaths.join(' ');
+        return text ? `${text} ${pathsString}` : pathsString;
+      }
+      return text;
+    },
+    [allDroppedFiles]
+  );
 
   const clearInputState = useCallback(() => {
     setDisplayValue('');
@@ -1189,7 +1191,13 @@ export default function ChatInput({
       onDrop={handleLocalDrop}
       onDragOver={handleLocalDragOver}
     >
-      <input ref={fileInputRef} type="file" onChange={handleFileInputChange} style={{ display: 'none' }} accept="*/*" />
+      <input
+        ref={fileInputRef}
+        type="file"
+        onChange={handleFileInputChange}
+        style={{ display: 'none' }}
+        accept="*/*"
+      />
       {/* Message Queue Display */}
       {queuedMessages.length > 0 && (
         <MessageQueue
@@ -1270,7 +1278,7 @@ export default function ChatInput({
                           <b>Models.</b>
                         </p>
                       ) : VOICE_DICTATION_ELEVENLABS_ENABLED &&
-                        dictationSettings.provider === 'elevenlabs' ? (
+                        dictationSettings.provider === DICTATION_PROVIDER_ELEVENLABS ? (
                         <p>
                           ElevenLabs API key is not configured. Set it up in <b>Settings</b> {'>'}{' '}
                           <b>Chat</b> {'>'} <b>Voice Dictation.</b>
diff --git a/ui/desktop/src/components/ConfigContext.tsx b/ui/desktop/src/components/ConfigContext.tsx
index add93c0cc00a..e2de27f30233 100644
--- a/ui/desktop/src/components/ConfigContext.tsx
+++ b/ui/desktop/src/components/ConfigContext.tsx
@@ -66,6 +66,10 @@ export const ConfigProvider: React.FC<ConfigProviderProps> = ({ children }) => {
   const [extensionsList, setExtensionsList] = useState<FixedExtensionEntry[]>([]);
   const [extensionWarnings, setExtensionWarnings] = useState<string[]>([]);
 
+  // Ref to access providersList in getProviders without recreating the callback
+  const providersListRef = React.useRef<ProviderDetails[]>(providersList);
+  providersListRef.current = providersList;
+
   const reloadConfig = useCallback(async () => {
     const response = await readAllConfig();
     setConfig(response.data?.config || {});
@@ -168,23 +172,20 @@ export const ConfigProvider: React.FC<ConfigProviderProps> = ({ children }) => {
     [addExtension, getExtensions]
   );
 
-  const getProviders = useCallback(
-    async (forceRefresh = false): Promise<ProviderDetails[]> => {
-      if (forceRefresh || providersList.length === 0) {
-        try {
-          const response = await providers();
-          const providersData = response.data || [];
-          setProvidersList(providersData);
-          return providersData;
-        } catch (error) {
-          console.error('Failed to fetch providers:', error);
-          return [];
-        }
+  const getProviders = useCallback(async (forceRefresh = false): Promise<ProviderDetails[]> => {
+    if (forceRefresh || providersListRef.current.length === 0) {
+      try {
+        const response = await providers();
+        const providersData = response.data || [];
+        setProvidersList(providersData);
+        return providersData;
+      } catch (error) {
+        console.error('Failed to fetch providers:', error);
+        return [];
       }
-      return providersList;
-    },
-    [providersList]
-  );
+    }
+    return providersListRef.current;
+  }, []);
 
   const getProviderModels = useCallback(async (providerName: string): Promise<string[]> => {
     try {
diff --git a/ui/desktop/src/components/bottom_menu/BottomMenuExtensionSelection.tsx b/ui/desktop/src/components/bottom_menu/BottomMenuExtensionSelection.tsx
index 3de8f3e3b82c..f1fa663ec8b8 100644
--- a/ui/desktop/src/components/bottom_menu/BottomMenuExtensionSelection.tsx
+++ b/ui/desktop/src/components/bottom_menu/BottomMenuExtensionSelection.tsx
@@ -28,6 +28,7 @@ export const BottomMenuExtensionSelection = ({ sessionId }: BottomMenuExtensionS
   const [pendingSort, setPendingSort] = useState(false);
   const [togglingExtension, setTogglingExtension] = useState<string | null>(null);
   const [refreshTrigger, setRefreshTrigger] = useState(0);
+  const [isSessionExtensionsLoaded, setIsSessionExtensionsLoaded] = useState(false);
   const sortTimeoutRef = useRef<ReturnType<typeof setTimeout> | null>(null);
   const { extensionsList: allExtensions } = useConfig();
   const isHubView = !sessionId;
@@ -70,12 +71,15 @@ export const BottomMenuExtensionSelection = ({ sessionId }: BottomMenuExtensionS
 
         if (response.data?.extensions) {
           setSessionExtensions(response.data.extensions);
+          setIsSessionExtensionsLoaded(true);
         }
       } catch (error) {
         console.error('Failed to fetch session extensions:', error);
+        setIsSessionExtensionsLoaded(true);
       }
     };
 
+    setIsSessionExtensionsLoaded(false);
     fetchExtensions();
   }, [sessionId, isOpen, refreshTrigger]);
 
@@ -225,7 +229,7 @@ export const BottomMenuExtensionSelection = ({ sessionId }: BottomMenuExtensionS
     >
       <DropdownMenuTrigger asChild>
         <button
-          className="flex items-center cursor-pointer [&_svg]:size-4 text-text-default/70 hover:text-text-default hover:scale-100 hover:bg-transparent text-xs"
+          className={`flex items-center [&_svg]:size-4 text-text-default/70 hover:text-text-default hover:scale-100 hover:bg-transparent text-xs cursor-pointer ${allExtensions.length === 0 || (!isHubView && !isSessionExtensionsLoaded) ? 'invisible' : ''}`}
           title="manage extensions"
         >
           <Puzzle className="mr-1 h-4 w-4" />
diff --git a/ui/desktop/src/components/settings/dictation/ElevenLabsKeyInput.tsx b/ui/desktop/src/components/settings/dictation/ElevenLabsKeyInput.tsx
index 4cce6d21f6b4..a305faf05404 100644
--- a/ui/desktop/src/components/settings/dictation/ElevenLabsKeyInput.tsx
+++ b/ui/desktop/src/components/settings/dictation/ElevenLabsKeyInput.tsx
@@ -1,7 +1,8 @@
 import { useState, useEffect, useRef } from 'react';
 import { Input } from '../../ui/input';
 import { useConfig } from '../../ConfigContext';
-import { ELEVENLABS_API_KEY } from '../../../hooks/dictationConstants';
+import { ELEVENLABS_API_KEY, isSecretKeyConfigured } from '../../../hooks/dictationConstants';
+import { setElevenLabsKeyCache } from '../../../hooks/useDictationSettings';
 
 export const ElevenLabsKeyInput = () => {
   const [elevenLabsApiKey, setElevenLabsApiKey] = useState('');
@@ -14,12 +15,16 @@ export const ElevenLabsKeyInput = () => {
     const loadKey = async () => {
       setIsLoadingKey(true);
       try {
-        const keyExists = await read(ELEVENLABS_API_KEY, true);
-        if (keyExists === true) {
+        const response = await read(ELEVENLABS_API_KEY, true);
+        if (isSecretKeyConfigured(response)) {
           setHasElevenLabsKey(true);
+          setElevenLabsKeyCache(true);
+        } else {
+          setElevenLabsKeyCache(false);
         }
       } catch (error) {
         console.error('Error checking ElevenLabs API key:', error);
+        setElevenLabsKeyCache(false);
       } finally {
         setIsLoadingKey(false);
       }
@@ -34,9 +39,11 @@ export const ElevenLabsKeyInput = () => {
       if (elevenLabsApiKeyRef.current) {
         const keyToSave = elevenLabsApiKeyRef.current;
         if (keyToSave.trim()) {
-          upsert(ELEVENLABS_API_KEY, keyToSave, true).catch((error) => {
-            console.error('Error saving ElevenLabs API key on unmount:', error);
-          });
+          upsert(ELEVENLABS_API_KEY, keyToSave, true)
+            .then(() => setElevenLabsKeyCache(true))
+            .catch((error) => {
+              console.error('Error saving ElevenLabs API key on unmount:', error);
+            });
         }
       }
     };
@@ -53,15 +60,13 @@ export const ElevenLabsKeyInput = () => {
   const saveElevenLabsKey = async () => {
     try {
       if (elevenLabsApiKey.trim()) {
-        console.log('Saving ElevenLabs API key to secure storage...');
         await upsert(ELEVENLABS_API_KEY, elevenLabsApiKey, true);
         setHasElevenLabsKey(true);
-        console.log('ElevenLabs API key saved successfully');
+        setElevenLabsKeyCache(true);
       } else {
-        console.log('Removing ElevenLabs API key from secure storage...');
         await upsert(ELEVENLABS_API_KEY, null, true);
         setHasElevenLabsKey(false);
-        console.log('ElevenLabs API key removed successfully');
+        setElevenLabsKeyCache(false);
       }
     } catch (error) {
       console.error('Error saving ElevenLabs API key:', error);
diff --git a/ui/desktop/src/components/settings/dictation/ProviderInfo.tsx b/ui/desktop/src/components/settings/dictation/ProviderInfo.tsx
index 5104502d206c..187f790d1f2f 100644
--- a/ui/desktop/src/components/settings/dictation/ProviderInfo.tsx
+++ b/ui/desktop/src/components/settings/dictation/ProviderInfo.tsx
@@ -1,4 +1,5 @@
 import { DictationProvider } from '../../../hooks/useDictationSettings';
+import { DICTATION_PROVIDER_ELEVENLABS } from '../../../hooks/dictationConstants';
 import { VOICE_DICTATION_ELEVENLABS_ENABLED } from '../../../updates';
 
 interface ProviderInfoProps {
@@ -16,7 +17,7 @@ export const ProviderInfo = ({ provider }: ProviderInfoProps) => {
           configured in the Models section.
         </p>
       )}
-      {VOICE_DICTATION_ELEVENLABS_ENABLED && provider === 'elevenlabs' && (
+      {VOICE_DICTATION_ELEVENLABS_ENABLED && provider === DICTATION_PROVIDER_ELEVENLABS && (
         <div>
           <p className="text-xs text-text-muted">
             Uses ElevenLabs speech-to-text API for high-quality transcription.
diff --git a/ui/desktop/src/components/settings/dictation/ProviderSelector.tsx b/ui/desktop/src/components/settings/dictation/ProviderSelector.tsx
index 479cd7b581b9..5c8e917d4356 100644
--- a/ui/desktop/src/components/settings/dictation/ProviderSelector.tsx
+++ b/ui/desktop/src/components/settings/dictation/ProviderSelector.tsx
@@ -1,6 +1,7 @@
 import { useState, useEffect } from 'react';
 import { ChevronDown } from 'lucide-react';
 import { DictationProvider, DictationSettings } from '../../../hooks/useDictationSettings';
+import { DICTATION_PROVIDER_ELEVENLABS } from '../../../hooks/dictationConstants';
 import { useConfig } from '../../ConfigContext';
 import { ElevenLabsKeyInput } from './ElevenLabsKeyInput';
 import { ProviderInfo } from './ProviderInfo';
@@ -57,7 +58,7 @@ export const ProviderSelector = ({ settings, onProviderChange }: ProviderSelecto
     switch (provider) {
       case 'openai':
         return 'OpenAI Whisper';
-      case 'elevenlabs':
+      case DICTATION_PROVIDER_ELEVENLABS:
         return 'ElevenLabs';
       default:
         return 'None (disabled)';
@@ -95,11 +96,13 @@ export const ProviderSelector = ({ settings, onProviderChange }: ProviderSelecto
 
               {VOICE_DICTATION_ELEVENLABS_ENABLED && (
                 <button
-                  onClick={() => handleProviderChange('elevenlabs')}
+                  onClick={() => handleProviderChange(DICTATION_PROVIDER_ELEVENLABS)}
                   className="w-full px-3 py-2 text-left text-sm hover:bg-background-subtle transition-colors text-text-default last:rounded-b-md"
                 >
                   ElevenLabs
-                  {settings.provider === 'elevenlabs' && <span className="float-right">✓</span>}
+                  {settings.provider === DICTATION_PROVIDER_ELEVENLABS && (
+                    <span className="float-right">✓</span>
+                  )}
                 </button>
               )}
             </div>
@@ -107,9 +110,8 @@ export const ProviderSelector = ({ settings, onProviderChange }: ProviderSelecto
         </div>
       </div>
 
-      {VOICE_DICTATION_ELEVENLABS_ENABLED && settings.provider === 'elevenlabs' && (
-        <ElevenLabsKeyInput />
-      )}
+      {VOICE_DICTATION_ELEVENLABS_ENABLED &&
+        settings.provider === DICTATION_PROVIDER_ELEVENLABS && <ElevenLabsKeyInput />}
 
       <ProviderInfo provider={settings.provider} />
     </div>
diff --git a/ui/desktop/src/components/settings/dictation/VoiceDictationToggle.tsx b/ui/desktop/src/components/settings/dictation/VoiceDictationToggle.tsx
index 57d59be4fb0a..dcb4fea9cec1 100644
--- a/ui/desktop/src/components/settings/dictation/VoiceDictationToggle.tsx
+++ b/ui/desktop/src/components/settings/dictation/VoiceDictationToggle.tsx
@@ -3,6 +3,7 @@ import { Switch } from '../../ui/switch';
 import { DictationProvider, DictationSettings } from '../../../hooks/useDictationSettings';
 import {
   DICTATION_SETTINGS_KEY,
+  DICTATION_PROVIDER_ELEVENLABS,
   getDefaultDictationSettings,
 } from '../../../hooks/dictationConstants';
 import { useConfig } from '../../ConfigContext';
@@ -28,7 +29,10 @@ export const VoiceDictationToggle = () => {
         loadedSettings = parsed;
 
         // If ElevenLabs is disabled and user has it selected, reset to OpenAI
-        if (!VOICE_DICTATION_ELEVENLABS_ENABLED && loadedSettings.provider === 'elevenlabs') {
+        if (
+          !VOICE_DICTATION_ELEVENLABS_ENABLED &&
+          loadedSettings.provider === DICTATION_PROVIDER_ELEVENLABS
+        ) {
           loadedSettings = {
             ...loadedSettings,
             provider: 'openai',
diff --git a/ui/desktop/src/hooks/dictationConstants.ts b/ui/desktop/src/hooks/dictationConstants.ts
index 972ba08b6cfa..c9c7ee65d9d5 100644
--- a/ui/desktop/src/hooks/dictationConstants.ts
+++ b/ui/desktop/src/hooks/dictationConstants.ts
@@ -2,6 +2,13 @@ import { DictationSettings, DictationProvider } from './useDictationSettings';
 
 export const DICTATION_SETTINGS_KEY = 'dictation_settings';
 export const ELEVENLABS_API_KEY = 'ELEVENLABS_API_KEY';
+export const DICTATION_PROVIDER_ELEVENLABS = 'elevenlabs' as const;
+
+export const isSecretKeyConfigured = (response: unknown): boolean =>
+  typeof response === 'object' &&
+  response !== null &&
+  'maskedValue' in response &&
+  !!(response as { maskedValue: string }).maskedValue;
 
 export const getDefaultDictationSettings = async (
   getProviders: (refresh: boolean) => Promise<Array<{ name: string; is_configured: boolean }>>
diff --git a/ui/desktop/src/hooks/useDictationSettings.ts b/ui/desktop/src/hooks/useDictationSettings.ts
index d6fe046b5a4a..778006f7e6d4 100644
--- a/ui/desktop/src/hooks/useDictationSettings.ts
+++ b/ui/desktop/src/hooks/useDictationSettings.ts
@@ -3,19 +3,27 @@ import { useConfig } from '../components/ConfigContext';
 import {
   DICTATION_SETTINGS_KEY,
   ELEVENLABS_API_KEY,
+  DICTATION_PROVIDER_ELEVENLABS,
   getDefaultDictationSettings,
+  isSecretKeyConfigured,
 } from './dictationConstants';
 
-export type DictationProvider = 'openai' | 'elevenlabs' | null;
+export type DictationProvider = 'openai' | typeof DICTATION_PROVIDER_ELEVENLABS | null;
 
 export interface DictationSettings {
   enabled: boolean;
   provider: DictationProvider;
 }
 
+let elevenLabsKeyCache: boolean | null = null;
+
+export const setElevenLabsKeyCache = (value: boolean) => {
+  elevenLabsKeyCache = value;
+};
+
 export const useDictationSettings = () => {
   const [settings, setSettings] = useState<DictationSettings | null>(null);
-  const [hasElevenLabsKey, setHasElevenLabsKey] = useState<boolean>(false);
+  const [hasElevenLabsKey, setHasElevenLabsKey] = useState<boolean>(elevenLabsKeyCache ?? false);
   const { read, getProviders } = useConfig();
 
   useEffect(() => {
@@ -23,22 +31,27 @@ export const useDictationSettings = () => {
       // Load settings from localStorage
       const saved = localStorage.getItem(DICTATION_SETTINGS_KEY);
 
+      let currentSettings: DictationSettings;
       if (saved) {
-        const parsedSettings = JSON.parse(saved);
-        setSettings(parsedSettings);
+        currentSettings = JSON.parse(saved);
       } else {
-        const defaultSettings = await getDefaultDictationSettings(getProviders);
-        setSettings(defaultSettings);
+        currentSettings = await getDefaultDictationSettings(getProviders);
       }
-
-      // Load ElevenLabs API key from storage (non-secret for frontend access)
-      try {
-        const keyExists = await read(ELEVENLABS_API_KEY, true);
-        if (keyExists === true) {
-          setHasElevenLabsKey(true);
+      setSettings(currentSettings);
+      if (
+        currentSettings.provider === DICTATION_PROVIDER_ELEVENLABS &&
+        elevenLabsKeyCache === null
+      ) {
+        try {
+          const response = await read(ELEVENLABS_API_KEY, true);
+          const hasKey = isSecretKeyConfigured(response);
+          elevenLabsKeyCache = hasKey;
+          setHasElevenLabsKey(hasKey);
+        } catch (error) {
+          elevenLabsKeyCache = false;
+          setHasElevenLabsKey(false);
+          console.error('[useDictationSettings] Error checking ElevenLabs API key:', error);
         }
-      } catch (error) {
-        console.error('[useDictationSettings] Error loading ElevenLabs API key:', error);
       }
     };
 
diff --git a/ui/desktop/src/hooks/useWhisper.ts b/ui/desktop/src/hooks/useWhisper.ts
index 385f674e9423..0cc557f807e6 100644
--- a/ui/desktop/src/hooks/useWhisper.ts
+++ b/ui/desktop/src/hooks/useWhisper.ts
@@ -2,6 +2,7 @@ import { useState, useRef, useCallback, useEffect } from 'react';
 import { useConfig } from '../components/ConfigContext';
 import { getApiUrl } from '../config';
 import { useDictationSettings } from './useDictationSettings';
+import { DICTATION_PROVIDER_ELEVENLABS } from './dictationConstants';
 import { safeJsonParse } from '../utils/conversionUtils';
 
 interface UseWhisperOptions {
@@ -77,7 +78,7 @@ export const useWhisper = ({ onTranscription, onError, onSizeWarning }: UseWhisp
       case 'openai':
         setCanUseDictation(hasOpenAIKey);
         break;
-      case 'elevenlabs':
+      case DICTATION_PROVIDER_ELEVENLABS:
         setCanUseDictation(hasElevenLabsKey);
         break;
       default:
@@ -180,7 +181,7 @@ export const useWhisper = ({ onTranscription, onError, onSizeWarning }: UseWhisp
           case 'openai':
             endpoint = '/audio/transcribe';
             break;
-          case 'elevenlabs':
+          case DICTATION_PROVIDER_ELEVENLABS:
             endpoint = '/audio/transcribe/elevenlabs';
             break;
           default:
@@ -373,5 +374,6 @@ export const useWhisper = ({ onTranscription, onError, onSizeWarning }: UseWhisp
     stopRecording,
     recordingDuration,
     estimatedSize,
+    dictationSettings,
   };
 };