diff --git a/packages/cli/src/config/settings.test.ts b/packages/cli/src/config/settings.test.ts
index 462a67d0b0..15a0535e0f 100644
--- a/packages/cli/src/config/settings.test.ts
+++ b/packages/cli/src/config/settings.test.ts
@@ -2200,6 +2200,18 @@ describe('Settings Loading and Merging', () => {
         allowMCPServers: ['serverA'],
       });
     });
+
+    it('should correctly migrate customWittyPhrases', () => {
+      const v2Settings: Partial<Settings> = {
+        ui: {
+          customWittyPhrases: ['test phrase'],
+        },
+      };
+      const v1Settings = migrateSettingsToV1(v2Settings as Settings);
+      expect(v1Settings).toEqual({
+        customWittyPhrases: ['test phrase'],
+      });
+    });
   });
 
   describe('loadEnvironment', () => {
@@ -2258,7 +2270,7 @@ describe('Settings Loading and Merging', () => {
     });
 
     it('should return false for settings that are already in V2 format', () => {
-      const v2Settings = {
+      const v2Settings: Partial<Settings> = {
         ui: {
           theme: 'dark',
         },
diff --git a/packages/cli/src/config/settings.ts b/packages/cli/src/config/settings.ts
index a02e3928df..97feb171b3 100644
--- a/packages/cli/src/config/settings.ts
+++ b/packages/cli/src/config/settings.ts
@@ -28,7 +28,7 @@ import {
   getSettingsSchema,
 } from './settingsSchema.js';
 import { resolveEnvVarsInObject } from '../utils/envVarResolver.js';
-import { customDeepMerge } from '../utils/deepMerge.js';
+import { customDeepMerge, type MergeableObject } from '../utils/deepMerge.js';
 import { updateSettingsFilePreservingFormat } from '../utils/commentJson.js';
 import { disableExtension } from './extension.js';
 
@@ -69,6 +69,7 @@ const MIGRATION_MAP: Record<string, string> = {
   coreTools: 'tools.core',
   contextFileName: 'context.fileName',
   customThemes: 'ui.customThemes',
+  customWittyPhrases: 'ui.customWittyPhrases',
   debugKeystrokeLogging: 'general.debugKeystrokeLogging',
   disableAutoUpdate: 'general.disableAutoUpdate',
   disableUpdateNag: 'general.disableUpdateNag',
@@ -252,7 +253,28 @@ function migrateSettingsToV2(
 
   // Carry over any unrecognized keys
   for (const remainingKey of flatKeys) {
-    v2Settings[remainingKey] = flatSettings[remainingKey];
+    const existingValue = v2Settings[remainingKey];
+    const newValue = flatSettings[remainingKey];
+
+    if (
+      typeof existingValue === 'object' &&
+      existingValue !== null &&
+      !Array.isArray(existingValue) &&
+      typeof newValue === 'object' &&
+      newValue !== null &&
+      !Array.isArray(newValue)
+    ) {
+      const pathAwareGetStrategy = (path: string[]) =>
+        getMergeStrategyForPath([remainingKey, ...path]);
+      v2Settings[remainingKey] = customDeepMerge(
+        pathAwareGetStrategy,
+        {},
+        newValue as MergeableObject,
+        existingValue as MergeableObject,
+      );
+    } else {
+      v2Settings[remainingKey] = newValue;
+    }
   }
 
   return v2Settings;
diff --git a/packages/cli/src/ui/AppContainer.tsx b/packages/cli/src/ui/AppContainer.tsx
index d9dec05d11..1c332ff432 100644
--- a/packages/cli/src/ui/AppContainer.tsx
+++ b/packages/cli/src/ui/AppContainer.tsx
@@ -833,8 +833,10 @@ Logging in with Google... Please restart Gemini CLI to continue.
     [handleSlashCommand, settings],
   );
 
-  const { elapsedTime, currentLoadingPhrase } =
-    useLoadingIndicator(streamingState);
+  const { elapsedTime, currentLoadingPhrase } = useLoadingIndicator(
+    streamingState,
+    settings.merged.ui?.customWittyPhrases,
+  );
 
   const handleExit = useCallback(
     (
diff --git a/packages/cli/src/utils/deepMerge.ts b/packages/cli/src/utils/deepMerge.ts
index e83c7a5203..85200ddbae 100644
--- a/packages/cli/src/utils/deepMerge.ts
+++ b/packages/cli/src/utils/deepMerge.ts
@@ -6,7 +6,7 @@
 
 import { MergeStrategy } from '../config/settingsSchema.js';
 
-type Mergeable =
+export type Mergeable =
   | string
   | number
   | boolean
@@ -15,7 +15,7 @@ type Mergeable =
   | object
   | Mergeable[];
 
-type MergeableObject = Record<string, Mergeable>;
+export type MergeableObject = Record<string, Mergeable>;
 
 function isPlainObject(item: unknown): item is MergeableObject {
   return !!item && typeof item === 'object' && !Array.isArray(item);