diff --git a/packages/cli/src/ui/AppContainer.test.tsx b/packages/cli/src/ui/AppContainer.test.tsx
index c8814969f7..d37f3961ce 100644
--- a/packages/cli/src/ui/AppContainer.test.tsx
+++ b/packages/cli/src/ui/AppContainer.test.tsx
@@ -1392,7 +1392,12 @@ describe('AppContainer State Management', () => {
         pressKey({ name: 'c', ctrl: true }, 2);
 
         expect(mockCancelOngoingRequest).toHaveBeenCalledTimes(2);
-        expect(mockHandleSlashCommand).toHaveBeenCalledWith('/quit');
+        expect(mockHandleSlashCommand).toHaveBeenCalledWith(
+          '/quit',
+          undefined,
+          undefined,
+          false,
+        );
         unmount();
       });
 
@@ -1432,7 +1437,12 @@ describe('AppContainer State Management', () => {
 
         pressKey({ name: 'd', ctrl: true }, 2);
 
-        expect(mockHandleSlashCommand).toHaveBeenCalledWith('/quit');
+        expect(mockHandleSlashCommand).toHaveBeenCalledWith(
+          '/quit',
+          undefined,
+          undefined,
+          false,
+        );
         unmount();
       });
 
diff --git a/packages/cli/src/ui/AppContainer.tsx b/packages/cli/src/ui/AppContainer.tsx
index a827483cd9..ee2c18d1a2 100644
--- a/packages/cli/src/ui/AppContainer.tsx
+++ b/packages/cli/src/ui/AppContainer.tsx
@@ -147,7 +147,9 @@ const SHELL_HEIGHT_PADDING = 10;
 
 export const AppContainer = (props: AppContainerProps) => {
   const { config, initializationResult, resumedSessionData } = props;
-  const historyManager = useHistory();
+  const historyManager = useHistory({
+    chatRecordingService: config.getGeminiClient()?.getChatRecordingService(),
+  });
   useMemoryMonitor(historyManager);
   const settings = useSettings();
   const isAlternateBuffer = useAlternateBuffer();
@@ -1026,7 +1028,7 @@ Logging in with Google... Please restart Gemini CLI to continue.
       recordExitFail(config);
     }
     if (ctrlCPressCount > 1) {
-      handleSlashCommand('/quit');
+      handleSlashCommand('/quit', undefined, undefined, false);
     } else {
       ctrlCTimerRef.current = setTimeout(() => {
         setCtrlCPressCount(0);
@@ -1044,7 +1046,7 @@ Logging in with Google... Please restart Gemini CLI to continue.
       recordExitFail(config);
     }
     if (ctrlDPressCount > 1) {
-      handleSlashCommand('/quit');
+      handleSlashCommand('/quit', undefined, undefined, false);
     } else {
       ctrlDTimerRef.current = setTimeout(() => {
         setCtrlDPressCount(0);
diff --git a/packages/cli/src/ui/commands/clearCommand.test.ts b/packages/cli/src/ui/commands/clearCommand.test.ts
index 5a261caa63..859c04a231 100644
--- a/packages/cli/src/ui/commands/clearCommand.test.ts
+++ b/packages/cli/src/ui/commands/clearCommand.test.ts
@@ -30,6 +30,7 @@ describe('clearCommand', () => {
 
   beforeEach(() => {
     mockResetChat = vi.fn().mockResolvedValue(undefined);
+    const mockGetChatRecordingService = vi.fn();
     vi.clearAllMocks();
 
     mockContext = createMockCommandContext({
@@ -38,7 +39,11 @@ describe('clearCommand', () => {
           getGeminiClient: () =>
             ({
               resetChat: mockResetChat,
+              getChat: () => ({
+                getChatRecordingService: mockGetChatRecordingService,
+              }),
             }) as unknown as GeminiClient,
+          setSessionId: vi.fn(),
         },
       },
     });
diff --git a/packages/cli/src/ui/commands/clearCommand.ts b/packages/cli/src/ui/commands/clearCommand.ts
index c3f0585951..eca35a58fd 100644
--- a/packages/cli/src/ui/commands/clearCommand.ts
+++ b/packages/cli/src/ui/commands/clearCommand.ts
@@ -7,6 +7,7 @@
 import { uiTelemetryService } from '@google/gemini-cli-core';
 import type { SlashCommand } from './types.js';
 import { CommandKind } from './types.js';
+import { randomUUID } from 'node:crypto';
 
 export const clearCommand: SlashCommand = {
   name: 'clear',
@@ -14,6 +15,11 @@ export const clearCommand: SlashCommand = {
   kind: CommandKind.BUILT_IN,
   action: async (context, _args) => {
     const geminiClient = context.services.config?.getGeminiClient();
+    const config = context.services.config;
+    const chatRecordingService = context.services.config
+      ?.getGeminiClient()
+      ?.getChat()
+      .getChatRecordingService();
 
     if (geminiClient) {
       context.ui.setDebugMessage('Clearing terminal and resetting chat.');
@@ -24,6 +30,13 @@ export const clearCommand: SlashCommand = {
       context.ui.setDebugMessage('Clearing terminal.');
     }
 
+    // Start a new conversation recording with a new session ID
+    if (config && chatRecordingService) {
+      const newSessionId = randomUUID();
+      config.setSessionId(newSessionId);
+      chatRecordingService.initialize();
+    }
+
     uiTelemetryService.setLastPromptTokenCount(0);
     context.ui.clear();
   },
diff --git a/packages/cli/src/ui/hooks/slashCommandProcessor.ts b/packages/cli/src/ui/hooks/slashCommandProcessor.ts
index fbceb3f664..59a5e8dade 100644
--- a/packages/cli/src/ui/hooks/slashCommandProcessor.ts
+++ b/packages/cli/src/ui/hooks/slashCommandProcessor.ts
@@ -311,6 +311,7 @@ export const useSlashCommandProcessor = (
       rawQuery: PartListUnion,
       oneTimeShellAllowlist?: Set<string>,
       overwriteConfirmed?: boolean,
+      addToHistory: boolean = true,
     ): Promise<SlashCommandProcessorResult | false> => {
       if (!commands) {
         return false;
@@ -326,8 +327,13 @@ export const useSlashCommandProcessor = (
 
       setIsProcessing(true);
 
-      const userMessageTimestamp = Date.now();
-      addItem({ type: MessageType.USER, text: trimmed }, userMessageTimestamp);
+      if (addToHistory) {
+        const userMessageTimestamp = Date.now();
+        addItem(
+          { type: MessageType.USER, text: trimmed },
+          userMessageTimestamp,
+        );
+      }
 
       let hasError = false;
       const {
diff --git a/packages/cli/src/ui/hooks/useEditorSettings.test.tsx b/packages/cli/src/ui/hooks/useEditorSettings.test.tsx
index 012daa4c35..2b39fae02c 100644
--- a/packages/cli/src/ui/hooks/useEditorSettings.test.tsx
+++ b/packages/cli/src/ui/hooks/useEditorSettings.test.tsx
@@ -21,12 +21,13 @@ import type {
   LoadedSettings,
 } from '../../config/settings.js';
 import { SettingScope } from '../../config/settings.js';
-import { MessageType, type HistoryItem } from '../types.js';
+import { MessageType } from '../types.js';
 import {
   type EditorType,
   checkHasEditorType,
   allowEditorTypeInSandbox,
 } from '@google/gemini-cli-core';
+import type { UseHistoryManagerReturn } from './useHistoryManager.js';
 
 import { SettingPaths } from '../../config/settingPaths.js';
 
@@ -45,9 +46,7 @@ const mockAllowEditorTypeInSandbox = vi.mocked(allowEditorTypeInSandbox);
 describe('useEditorSettings', () => {
   let mockLoadedSettings: LoadedSettings;
   let mockSetEditorError: MockedFunction<(error: string | null) => void>;
-  let mockAddItem: MockedFunction<
-    (item: Omit<HistoryItem, 'id'>, timestamp: number) => void
-  >;
+  let mockAddItem: MockedFunction<UseHistoryManagerReturn['addItem']>;
   let result: ReturnType<typeof useEditorSettings>;
 
   function TestComponent() {
diff --git a/packages/cli/src/ui/hooks/useEditorSettings.ts b/packages/cli/src/ui/hooks/useEditorSettings.ts
index 962d085f12..fa15202661 100644
--- a/packages/cli/src/ui/hooks/useEditorSettings.ts
+++ b/packages/cli/src/ui/hooks/useEditorSettings.ts
@@ -9,13 +9,14 @@ import type {
   LoadableSettingScope,
   LoadedSettings,
 } from '../../config/settings.js';
-import { type HistoryItem, MessageType } from '../types.js';
+import { MessageType } from '../types.js';
 import type { EditorType } from '@google/gemini-cli-core';
 import {
   allowEditorTypeInSandbox,
   checkHasEditorType,
   getEditorDisplayName,
 } from '@google/gemini-cli-core';
+import type { UseHistoryManagerReturn } from './useHistoryManager.js';
 
 import { SettingPaths } from '../../config/settingPaths.js';
 
@@ -32,7 +33,7 @@ interface UseEditorSettingsReturn {
 export const useEditorSettings = (
   loadedSettings: LoadedSettings,
   setEditorError: (error: string | null) => void,
-  addItem: (item: Omit<HistoryItem, 'id'>, timestamp: number) => void,
+  addItem: UseHistoryManagerReturn['addItem'],
 ): UseEditorSettingsReturn => {
   const [isEditorDialogOpen, setIsEditorDialogOpen] = useState(false);
 
diff --git a/packages/cli/src/ui/hooks/useHistoryManager.ts b/packages/cli/src/ui/hooks/useHistoryManager.ts
index c25fc84a29..66eff02824 100644
--- a/packages/cli/src/ui/hooks/useHistoryManager.ts
+++ b/packages/cli/src/ui/hooks/useHistoryManager.ts
@@ -6,6 +6,7 @@
 
 import { useState, useRef, useCallback, useMemo } from 'react';
 import type { HistoryItem } from '../types.js';
+import type { ChatRecordingService } from '@google/gemini-cli-core/src/services/chatRecordingService.js';
 
 // Type for the updater function passed to updateHistoryItem
 type HistoryItemUpdater = (
@@ -14,7 +15,11 @@ type HistoryItemUpdater = (
 
 export interface UseHistoryManagerReturn {
   history: HistoryItem[];
-  addItem: (itemData: Omit<HistoryItem, 'id'>, baseTimestamp: number) => number; // Returns the generated ID
+  addItem: (
+    itemData: Omit<HistoryItem, 'id'>,
+    baseTimestamp: number,
+    isResuming?: boolean,
+  ) => number; // Returns the generated ID
   updateItem: (
     id: number,
     updates: Partial<Omit<HistoryItem, 'id'>> | HistoryItemUpdater,
@@ -29,7 +34,11 @@ export interface UseHistoryManagerReturn {
  * Encapsulates the history array, message ID generation, adding items,
  * updating items, and clearing the history.
  */
-export function useHistory(): UseHistoryManagerReturn {
+export function useHistory({
+  chatRecordingService,
+}: {
+  chatRecordingService?: ChatRecordingService | null;
+} = {}): UseHistoryManagerReturn {
   const [history, setHistory] = useState<HistoryItem[]>([]);
   const messageIdCounterRef = useRef(0);
 
@@ -45,7 +54,11 @@ export function useHistory(): UseHistoryManagerReturn {
 
   // Adds a new item to the history state with a unique ID.
   const addItem = useCallback(
-    (itemData: Omit<HistoryItem, 'id'>, baseTimestamp: number): number => {
+    (
+      itemData: Omit<HistoryItem, 'id'>,
+      baseTimestamp: number,
+      isResuming: boolean = false,
+    ): number => {
       const id = getNextMessageId(baseTimestamp);
       const newItem: HistoryItem = { ...itemData, id } as HistoryItem;
 
@@ -63,9 +76,47 @@ export function useHistory(): UseHistoryManagerReturn {
         }
         return [...prevHistory, newItem];
       });
+
+      // Record UI-specific messages, but don't do it if we're actually loading
+      // an existing session.
+      if (!isResuming && chatRecordingService) {
+        switch (itemData.type) {
+          case 'compression':
+          case 'info':
+            chatRecordingService?.recordMessage({
+              model: undefined,
+              type: 'info',
+              content: itemData.text ?? '',
+            });
+            break;
+          case 'warning':
+            chatRecordingService?.recordMessage({
+              model: undefined,
+              type: 'warning',
+              content: itemData.text ?? '',
+            });
+            break;
+          case 'error':
+            chatRecordingService?.recordMessage({
+              model: undefined,
+              type: 'error',
+              content: itemData.text ?? '',
+            });
+            break;
+          case 'user':
+          case 'gemini':
+          case 'gemini_content':
+            // Core conversation recording handled by GeminiChat.
+            break;
+          default:
+            // Ignore the rest.
+            break;
+        }
+      }
+
       return id; // Return the generated ID (even if not added, to keep signature)
     },
-    [getNextMessageId],
+    [getNextMessageId, chatRecordingService],
   );
 
   /**
diff --git a/packages/cli/src/ui/hooks/useSessionBrowser.test.ts b/packages/cli/src/ui/hooks/useSessionBrowser.test.ts
index 6cf878dcd1..3face81079 100644
--- a/packages/cli/src/ui/hooks/useSessionBrowser.test.ts
+++ b/packages/cli/src/ui/hooks/useSessionBrowser.test.ts
@@ -55,6 +55,47 @@ describe('convertSessionToHistoryFormats', () => {
     });
   });
 
+  it('should convert system, warning, and error messages to appropriate types', () => {
+    const messages: MessageRecord[] = [
+      {
+        id: 'msg-1',
+        timestamp: '2025-01-01T00:01:00Z',
+        content: 'System message',
+        type: 'info',
+      },
+      {
+        id: 'msg-2',
+        timestamp: '2025-01-01T00:02:00Z',
+        content: 'Warning message',
+        type: 'warning',
+      },
+      {
+        id: 'msg-3',
+        timestamp: '2025-01-01T00:03:00Z',
+        content: 'Error occurred',
+        type: 'error',
+      },
+    ];
+
+    const result = convertSessionToHistoryFormats(messages);
+
+    expect(result.uiHistory[0]).toEqual({
+      type: MessageType.INFO,
+      text: 'System message',
+    });
+    expect(result.uiHistory[1]).toEqual({
+      type: MessageType.WARNING,
+      text: 'Warning message',
+    });
+    expect(result.uiHistory[2]).toEqual({
+      type: MessageType.ERROR,
+      text: 'Error occurred',
+    });
+
+    // System, warning, and error messages should not be included in client history
+    expect(result.clientHistory).toEqual([]);
+  });
+
   it('should filter out slash commands from client history', () => {
     const messages: MessageRecord[] = [
       {
diff --git a/packages/cli/src/ui/hooks/useSessionBrowser.ts b/packages/cli/src/ui/hooks/useSessionBrowser.ts
index 9f159aac4d..69a787b030 100644
--- a/packages/cli/src/ui/hooks/useSessionBrowser.ts
+++ b/packages/cli/src/ui/hooks/useSessionBrowser.ts
@@ -29,6 +29,15 @@ export function convertSessionToHistoryFormats(
         case 'user':
           messageType = MessageType.USER;
           break;
+        case 'info':
+          messageType = MessageType.INFO;
+          break;
+        case 'error':
+          messageType = MessageType.ERROR;
+          break;
+        case 'warning':
+          messageType = MessageType.WARNING;
+          break;
         default:
           messageType = MessageType.GEMINI;
           break;
@@ -70,9 +79,9 @@ export function convertSessionToHistoryFormats(
 
   for (const msg of messages) {
     // Skip system/error messages and user slash commands
-    // if (msg.type === 'system' || msg.type === 'error') {
-    //   continue;
-    // }
+    if (msg.type === 'info' || msg.type === 'error' || msg.type === 'warning') {
+      continue;
+    }
 
     if (msg.type === 'user') {
       // Skip user slash commands
@@ -91,8 +100,7 @@ export function convertSessionToHistoryFormats(
       });
     } else if (msg.type === 'gemini') {
       // Handle Gemini messages with potential tool calls
-      const hasToolCalls =
-        'toolCalls' in msg && msg.toolCalls && msg.toolCalls.length > 0;
+      const hasToolCalls = msg.toolCalls && msg.toolCalls.length > 0;
 
       if (hasToolCalls) {
         // Create model message with function calls
diff --git a/packages/cli/src/ui/hooks/useSessionResume.test.ts b/packages/cli/src/ui/hooks/useSessionResume.test.ts
index 93787b8d50..e135006471 100644
--- a/packages/cli/src/ui/hooks/useSessionResume.test.ts
+++ b/packages/cli/src/ui/hooks/useSessionResume.test.ts
@@ -101,11 +101,13 @@ describe('useSessionResume', () => {
         1,
         { type: 'user', text: 'Hello' },
         0,
+        true,
       );
       expect(mockHistoryManager.addItem).toHaveBeenNthCalledWith(
         2,
         { type: 'gemini', text: 'Hi there!' },
         1,
+        true,
       );
       expect(mockRefreshStatic).toHaveBeenCalled();
       expect(mockGeminiClient.resumeChat).toHaveBeenCalledWith(
@@ -328,11 +330,13 @@ describe('useSessionResume', () => {
         1,
         { type: 'user', text: 'Hello from resumed session' },
         0,
+        true,
       );
       expect(mockHistoryManager.addItem).toHaveBeenNthCalledWith(
         2,
         { type: 'gemini', text: 'Welcome back!' },
         1,
+        true,
       );
       expect(mockGeminiClient.resumeChat).toHaveBeenCalled();
     });
diff --git a/packages/cli/src/ui/hooks/useSessionResume.ts b/packages/cli/src/ui/hooks/useSessionResume.ts
index e738b5ce56..9eea8726d3 100644
--- a/packages/cli/src/ui/hooks/useSessionResume.ts
+++ b/packages/cli/src/ui/hooks/useSessionResume.ts
@@ -59,7 +59,7 @@ export function useSessionResume({
       setQuittingMessages(null);
       historyManagerRef.current.clearItems();
       uiHistory.forEach((item, index) => {
-        historyManagerRef.current.addItem(item, index);
+        historyManagerRef.current.addItem(item, index, true);
       });
       refreshStaticRef.current(); // Force Static component to re-render with the updated history.
 
diff --git a/packages/cli/src/ui/hooks/useThemeCommand.ts b/packages/cli/src/ui/hooks/useThemeCommand.ts
index 72133e9b11..47252b9aff 100644
--- a/packages/cli/src/ui/hooks/useThemeCommand.ts
+++ b/packages/cli/src/ui/hooks/useThemeCommand.ts
@@ -10,8 +10,9 @@ import type {
   LoadableSettingScope,
   LoadedSettings,
 } from '../../config/settings.js'; // Import LoadedSettings, AppSettings, MergedSetting
-import { type HistoryItem, MessageType } from '../types.js';
+import { MessageType } from '../types.js';
 import process from 'node:process';
+import type { UseHistoryManagerReturn } from './useHistoryManager.js';
 
 interface UseThemeCommandReturn {
   isThemeDialogOpen: boolean;
@@ -24,7 +25,7 @@ interface UseThemeCommandReturn {
 export const useThemeCommand = (
   loadedSettings: LoadedSettings,
   setThemeError: (error: string | null) => void,
-  addItem: (item: Omit<HistoryItem, 'id'>, timestamp: number) => void,
+  addItem: UseHistoryManagerReturn['addItem'],
   initialThemeError: string | null,
 ): UseThemeCommandReturn => {
   const [isThemeDialogOpen, setIsThemeDialogOpen] =
diff --git a/packages/core/src/services/chatRecordingService.ts b/packages/core/src/services/chatRecordingService.ts
index 2ac9f4d99a..5bd9533bf1 100644
--- a/packages/core/src/services/chatRecordingService.ts
+++ b/packages/core/src/services/chatRecordingService.ts
@@ -62,7 +62,7 @@ export interface ToolCallRecord {
  */
 export type ConversationRecordExtra =
   | {
-      type: 'user';
+      type: 'user' | 'info' | 'error' | 'warning';
     }
   | {
       type: 'gemini';