diff --git a/src-tauri/src/ipc.rs b/src-tauri/src/ipc.rs
index 6f3edee..b40e997 100644
--- a/src-tauri/src/ipc.rs
+++ b/src-tauri/src/ipc.rs
@@ -278,6 +278,8 @@ pub struct PersistedSettings {
     // frontend. The field is kept on legacy persisted JSON only; serde ignores
     // unknown fields when decoding, so existing installs migrate cleanly.
     pub auto_check_updates: bool,
+    #[serde(default)]
+    pub keychain_access_granted: bool,
 }
 
 #[derive(Clone, Debug, Serialize, TS)]
diff --git a/src-tauri/src/settings.rs b/src-tauri/src/settings.rs
index 6e51be5..a80f3aa 100644
--- a/src-tauri/src/settings.rs
+++ b/src-tauri/src/settings.rs
@@ -289,6 +289,7 @@ fn default_settings() -> PersistedSettings {
         media_cookie_source: MediaCookieSource::None,
         site_logins: Vec::new(),
         auto_check_updates: true,
+        keychain_access_granted: false,
     }
 }
 
diff --git a/src/bindings/PersistedSettings.ts b/src/bindings/PersistedSettings.ts
index c2c90ad..91c90bc 100644
--- a/src/bindings/PersistedSettings.ts
+++ b/src/bindings/PersistedSettings.ts
@@ -8,4 +8,4 @@ import type { SettingsTab } from "./SettingsTab";
 import type { SiteLogin } from "./SiteLogin";
 import type { Theme } from "./Theme";
 
-export type PersistedSettings = { theme: Theme, baseDownloadFolder: string, categorySubfolders: { [key in string]: string }, categoryDirectoryOverrides: { [key in string]: string }, approvedDownloadRoots: Array<string>, maxConcurrentDownloads: number, globalSpeedLimit: string, isSidebarVisible: boolean, activeSettingsTab: SettingsTab, scheduler: SchedulerSettings, schedulerRunning: boolean, schedulerActiveDownloadIds: Array<string>, schedulerLastStartKey: string, schedulerLastStopKey: string, lastCustomSpeedLimitKiB: number, perServerConnections: number, maxAutomaticRetries: number, showNotifications: boolean, playCompletionSound: boolean, appFontSize: AppFontSize, listRowDensity: ListRowDensity, showDockBadge: boolean, showMenuBarIcon: boolean, proxyMode: ProxyMode, proxyHost: string, proxyPort: number, customUserAgent: string, askWhereToSaveEachFile: boolean, preventsSleepWhileDownloading: boolean, mediaCookieSource: MediaCookieSource, siteLogins: Array<SiteLogin>, autoCheckUpdates: boolean, };
+export type PersistedSettings = { theme: Theme, baseDownloadFolder: string, categorySubfolders: { [key in string]: string }, categoryDirectoryOverrides: { [key in string]: string }, approvedDownloadRoots: Array<string>, maxConcurrentDownloads: number, globalSpeedLimit: string, isSidebarVisible: boolean, activeSettingsTab: SettingsTab, scheduler: SchedulerSettings, schedulerRunning: boolean, schedulerActiveDownloadIds: Array<string>, schedulerLastStartKey: string, schedulerLastStopKey: string, lastCustomSpeedLimitKiB: number, perServerConnections: number, maxAutomaticRetries: number, showNotifications: boolean, playCompletionSound: boolean, appFontSize: AppFontSize, listRowDensity: ListRowDensity, showDockBadge: boolean, showMenuBarIcon: boolean, proxyMode: ProxyMode, proxyHost: string, proxyPort: number, customUserAgent: string, askWhereToSaveEachFile: boolean, preventsSleepWhileDownloading: boolean, mediaCookieSource: MediaCookieSource, siteLogins: Array<SiteLogin>, autoCheckUpdates: boolean, keychainAccessGranted: boolean, };
diff --git a/src/components/KeychainPermissionModal.tsx b/src/components/KeychainPermissionModal.tsx
index 59e3a1a..79e5ce2 100644
--- a/src/components/KeychainPermissionModal.tsx
+++ b/src/components/KeychainPermissionModal.tsx
@@ -19,6 +19,7 @@ export const KeychainPermissionModal: React.FC = () => {
     try {
       const result = await invoke('grant_keychain_access');
       if (result.persistent) {
+        useSettingsStore.setState({ keychainAccessGranted: true });
         await useSettingsStore.getState().hydratePairingToken();
         setShowKeychainModal(false);
       } else {
diff --git a/src/components/SettingsView.tsx b/src/components/SettingsView.tsx
index d6c6422..dd3e4ce 100644
--- a/src/components/SettingsView.tsx
+++ b/src/components/SettingsView.tsx
@@ -8,7 +8,7 @@ import {
 } from '../store/useSettingsStore';
 import {
   Download, Palette, Globe, Folder, Key,
-  Moon, Terminal, Puzzle, Info, Plus, Trash2, Copy, RefreshCw, Code, ShieldAlert
+  Moon, Terminal, Puzzle, Info, Plus, Trash2, Copy, RefreshCw, Code, ShieldAlert, Check
 } from 'lucide-react';
 import { open } from '@tauri-apps/plugin-dialog';
 import { getVersion } from '@tauri-apps/api/app';
@@ -1055,7 +1055,19 @@ className="app-button px-3 py-1.5 text-[12px] flex items-center gap-1.5 disabled
                 </div>
               </div>
 
-              {!settings.isPairingTokenPersistent && (
+              {settings.isPairingTokenPersistent ? (
+                <div className="bg-green-500/10 border border-green-500/20 rounded-lg p-3 flex items-center gap-3">
+                  <div className="p-1.5 bg-green-500/20 rounded-full text-green-500 flex-shrink-0">
+                    <Check size={16} strokeWidth={2.5} />
+                  </div>
+                  <div className="flex-1">
+                    <h4 className="text-sm font-semibold text-green-500 m-0">Keychain Access Granted</h4>
+                    <p className="text-xs text-text-secondary m-0 mt-0.5">
+                      Your pairing token is securely saved and will persist across restarts.
+                    </p>
+                  </div>
+                </div>
+              ) : (
                 <div className="bg-orange-500/10 border border-orange-500/20 rounded-lg p-4 flex items-start gap-3">
                   <ShieldAlert className="w-5 h-5 text-orange-500 flex-shrink-0 mt-0.5" />
                   <div className="flex-1">
@@ -1066,7 +1078,7 @@ className="app-button px-3 py-1.5 text-[12px] flex items-center gap-1.5 disabled
                     </p>
                     <button 
                       onClick={() => settings.setShowKeychainModal(true)}
-                      className="app-button primary text-xs py-1"
+                      className="px-4 py-1.5 rounded-md text-xs font-medium transition-colors bg-accent text-white hover:bg-accent/90 shadow-sm"
                     >
                       Grant Keychain Access
                     </button>
diff --git a/src/store/useSettingsStore.ts b/src/store/useSettingsStore.ts
index 3a7c4bd..beeca6d 100644
--- a/src/store/useSettingsStore.ts
+++ b/src/store/useSettingsStore.ts
@@ -106,6 +106,7 @@ export interface SettingsState {
   siteLogins: SiteLogin[];
   extensionPairingToken: string;
   isPairingTokenPersistent: boolean;
+  keychainAccessGranted: boolean;
   autoCheckUpdates: boolean;
   showKeychainModal: boolean;
 
@@ -178,7 +179,7 @@ const generateSecureToken = () => {
 
 export const useSettingsStore = create<SettingsState>()(
   persist(
-    (set) => ({
+    (set, get) => ({
       theme: 'system',
       baseDownloadFolder: '~/Downloads',
       categorySubfolders: { ...DEFAULT_CATEGORY_SUBFOLDERS },
@@ -224,6 +225,7 @@ export const useSettingsStore = create<SettingsState>()(
       siteLogins: [],
       extensionPairingToken: '',
       isPairingTokenPersistent: true,
+      keychainAccessGranted: false,
       autoCheckUpdates: true,
       showKeychainModal: false,
 
@@ -314,7 +316,8 @@ export const useSettingsStore = create<SettingsState>()(
         set({ extensionPairingToken: token });
       },
       hydratePairingToken: async () => {
-        const result = await invoke('hydrate_extension_pairing_token');
+        const granted = get().keychainAccessGranted;
+        const result = await invoke(granted ? 'grant_keychain_access' : 'hydrate_extension_pairing_token');
         set({ 
           extensionPairingToken: result.token,
           isPairingTokenPersistent: result.persistent 
@@ -324,8 +327,8 @@ export const useSettingsStore = create<SettingsState>()(
         }
         return result.tokenChanged;
       },
-      setAutoCheckUpdates: (autoCheckUpdates) => set({ autoCheckUpdates }),
-      setShowKeychainModal: (show) => set({ showKeychainModal: show }),
+      setAutoCheckUpdates: (autoCheckUpdates: boolean) => set({ autoCheckUpdates }),
+      setShowKeychainModal: (show: boolean) => set({ showKeychainModal: show }),
     }),
     {
       name: 'firelink-settings',
@@ -393,6 +396,7 @@ export const useSettingsStore = create<SettingsState>()(
         preventsSleepWhileDownloading: state.preventsSleepWhileDownloading,
         mediaCookieSource: state.mediaCookieSource,
         siteLogins: state.siteLogins,
+        keychainAccessGranted: state.keychainAccessGranted,
         autoCheckUpdates: state.autoCheckUpdates
       }),
       merge: (persistedState: unknown, currentState) => {