diff --git a/packages/core/src/core/geminiChat.ts b/packages/core/src/core/geminiChat.ts
index ae5f46db37..df522c6eb4 100644
--- a/packages/core/src/core/geminiChat.ts
+++ b/packages/core/src/core/geminiChat.ts
@@ -255,7 +255,7 @@ export class GeminiChat {
   ) {
     validateHistory(history);
     this.chatRecordingService = new ChatRecordingService(config);
-    this.chatRecordingService.initialize(resumedSessionData, kind);
+    this.chatRecordingService.initialize(resumedSessionData, kind, history);
     this.lastPromptTokenCount = estimateTokenCountSync(
       this.history.flatMap((c) => c.parts || []),
     );
diff --git a/packages/core/src/services/chatRecordingService.test.ts b/packages/core/src/services/chatRecordingService.test.ts
index 5aaa0a2538..bc2e9375a2 100644
--- a/packages/core/src/services/chatRecordingService.test.ts
+++ b/packages/core/src/services/chatRecordingService.test.ts
@@ -122,6 +122,50 @@ describe('ChatRecordingService', () => {
       const conversation = JSON.parse(fs.readFileSync(sessionFile, 'utf8'));
       expect(conversation.sessionId).toBe('old-session-id');
     });
+
+    it('should overwrite existing messages if initialHistory is provided', () => {
+      const chatsDir = path.join(testTempDir, 'chats');
+      fs.mkdirSync(chatsDir, { recursive: true });
+      const sessionFile = path.join(chatsDir, 'session-overwrite.json');
+      const initialData = {
+        sessionId: 'test-session-id',
+        projectHash: 'test-project-hash',
+        messages: [
+          {
+            id: 'msg-1',
+            type: 'user',
+            content: 'Old Message',
+            timestamp: new Date().toISOString(),
+          },
+        ],
+      };
+      fs.writeFileSync(sessionFile, JSON.stringify(initialData));
+
+      const newHistory: Content[] = [
+        {
+          role: 'user',
+          parts: [{ text: 'Compressed Summary' }],
+        },
+      ];
+
+      chatRecordingService.initialize(
+        {
+          filePath: sessionFile,
+          conversation: initialData as ConversationRecord,
+        },
+        'main',
+        newHistory,
+      );
+
+      const conversation = JSON.parse(
+        fs.readFileSync(sessionFile, 'utf8'),
+      ) as ConversationRecord;
+      expect(conversation.messages).toHaveLength(1);
+      expect(conversation.messages[0].content).toEqual([
+        { text: 'Compressed Summary' },
+      ]);
+      expect(conversation.messages[0].type).toBe('user');
+    });
   });
 
   describe('recordMessage', () => {
diff --git a/packages/core/src/services/chatRecordingService.ts b/packages/core/src/services/chatRecordingService.ts
index 1748ccbe20..d970dc01b5 100644
--- a/packages/core/src/services/chatRecordingService.ts
+++ b/packages/core/src/services/chatRecordingService.ts
@@ -147,10 +147,14 @@ export class ChatRecordingService {
    *
    * @param resumedSessionData Data from a previous session to resume from.
    * @param kind The kind of conversation (main or subagent).
+   * @param initialHistory The starting history for this session. If provided when resuming an
+   * existing session (e.g., after chat compression), this will overwrite the messages currently
+   * stored on disk to ensure the file reflects the new session state.
    */
   initialize(
     resumedSessionData?: ResumedSessionData,
     kind?: 'main' | 'subagent',
+    initialHistory?: Content[],
   ): void {
     try {
       this.kind = kind;
@@ -163,6 +167,10 @@ export class ChatRecordingService {
         // Update the session ID in the existing file
         this.updateConversation((conversation) => {
           conversation.sessionId = this.sessionId;
+          if (initialHistory) {
+            conversation.messages =
+              this.apiContentToMessageRecords(initialHistory);
+          }
         });
 
         // Clear any cached data to force fresh reads
@@ -190,7 +198,7 @@ export class ChatRecordingService {
           projectHash: this.projectHash,
           startTime: new Date().toISOString(),
           lastUpdated: new Date().toISOString(),
-          messages: [],
+          messages: this.apiContentToMessageRecords(initialHistory || []),
           kind: this.kind,
         });
       }
@@ -215,6 +223,24 @@ export class ChatRecordingService {
     }
   }
 
+  /**
+   * Converts API Content array to storage-compatible MessageRecord array.
+   */
+  private apiContentToMessageRecords(history: Content[]): MessageRecord[] {
+    return history.map((content) => {
+      const type = content.role === 'model' ? 'gemini' : 'user';
+      const record = {
+        id: randomUUID(),
+        timestamp: new Date().toISOString(),
+        type,
+        content: content.parts,
+      };
+
+      // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
+      return record as MessageRecord;
+    });
+  }
+
   private getLastMessage(
     conversation: ConversationRecord,
   ): MessageRecord | undefined {