diff --git a/packages/cli/src/ui/commands/chatCommand.ts b/packages/cli/src/ui/commands/chatCommand.ts
index 2efdc24eb3..9067828f2f 100644
--- a/packages/cli/src/ui/commands/chatCommand.ts
+++ b/packages/cli/src/ui/commands/chatCommand.ts
@@ -183,9 +183,9 @@ const resumeCheckpointCommand: SlashCommand = {
     const config = context.services.agentContext?.config;
     await logger.initialize();
     const checkpoint = await logger.loadCheckpoint(tag);
-    const conversation = checkpoint.history;
+    const conversation = checkpoint.history ?? [];
 
-    if (conversation.length === 0) {
+    if (conversation.length === 0 && !checkpoint.messages) {
       return {
         type: 'message',
         messageType: 'info',
@@ -233,6 +233,8 @@ const resumeCheckpointCommand: SlashCommand = {
       type: 'load_history',
       history: uiHistory,
       clientHistory: conversation,
+      messages: checkpoint.messages,
+      version: checkpoint.version,
     };
   },
   completion: async (context, partialArg) => {
diff --git a/packages/cli/src/ui/hooks/slashCommandProcessor.ts b/packages/cli/src/ui/hooks/slashCommandProcessor.ts
index 6e880ed4bb..04ae67a758 100644
--- a/packages/cli/src/ui/hooks/slashCommandProcessor.ts
+++ b/packages/cli/src/ui/hooks/slashCommandProcessor.ts
@@ -549,7 +549,16 @@ export const useSlashCommandProcessor = (
                     }
                   }
                 case 'load_history': {
-                  config?.getGeminiClient()?.setHistory(result.clientHistory);
+                  const client = config?.getGeminiClient();
+                  if (result.version === '2.0' && client) {
+                    await client.resumeChat(
+                      [...result.clientHistory],
+                      undefined,
+                      result.messages,
+                    );
+                  } else {
+                    client?.setHistory(result.clientHistory);
+                  }
                   fullCommandContext.ui.clear();
                   result.history.forEach((item, index) => {
                     fullCommandContext.ui.addItem(item, index);
diff --git a/packages/core/src/commands/types.ts b/packages/core/src/commands/types.ts
index 62bda279af..32dd76a3a9 100644
--- a/packages/core/src/commands/types.ts
+++ b/packages/core/src/commands/types.ts
@@ -5,6 +5,8 @@
  */
 
 import type { Content, PartListUnion } from '@google/genai';
+import type { MessageRecord } from '../services/chatRecordingTypes.js';
+
 /**
  * The return type for a command action that results in scheduling a tool call.
  */
@@ -37,6 +39,8 @@ export interface LoadHistoryActionReturn<HistoryType = unknown> {
   type: 'load_history';
   history: HistoryType;
   clientHistory: readonly Content[]; // The history for the generative client
+  messages?: MessageRecord[];
+  version?: '2.0';
 }
 
 /**
diff --git a/packages/core/src/core/logger.test.ts b/packages/core/src/core/logger.test.ts
index 53a0a10208..e84dcf9317 100644
--- a/packages/core/src/core/logger.test.ts
+++ b/packages/core/src/core/logger.test.ts
@@ -546,6 +546,33 @@ describe('Logger', () => {
       expect(loaded).toEqual({ history: conversation, messages: [] });
     });
 
+    it('should load a version 2.0 checkpoint and reconstruct history', async () => {
+      const tag = 'v2-tag';
+      const v2Checkpoint = {
+        version: '2.0',
+        history: [{ role: 'user', parts: [{ text: 'preserved' }] }],
+        messages: [
+          {
+            id: '1',
+            type: 'user',
+            content: 'hello',
+            timestamp: '2025-01-01T12:00:00.000Z',
+          },
+        ],
+      };
+      const taggedFilePath = path.join(
+        TEST_GEMINI_DIR,
+        'checkpoint-v2-tag.json',
+      );
+      await fs.writeFile(taggedFilePath, JSON.stringify(v2Checkpoint, null, 2));
+
+      const loaded = await logger.loadCheckpoint(tag);
+      expect(loaded.messages).toEqual(v2Checkpoint.messages);
+      expect(loaded.history).toEqual([
+        { role: 'user', parts: [{ text: 'hello' }] },
+      ]);
+    });
+
     it('should return an empty message list if a tagged checkpoint file does not exist', async () => {
       const loaded = await logger.loadCheckpoint('nonexistent-tag');
       expect(loaded).toEqual({ history: [], messages: [] });
diff --git a/packages/core/src/core/logger.ts b/packages/core/src/core/logger.ts
index feaf6c5a61..cc1e38b794 100644
--- a/packages/core/src/core/logger.ts
+++ b/packages/core/src/core/logger.ts
@@ -11,6 +11,7 @@ import type { AuthType } from './contentGenerator.js';
 import type { Storage } from '../config/storage.js';
 import { debugLogger } from '../utils/debugLogger.js';
 import { coreEvents } from '../utils/events.js';
+import { reconstructHistory } from '../utils/history-reconstruction.js';
 
 import {
   type ConversationRecord,
@@ -32,7 +33,11 @@ export interface LogEntry {
 }
 
 export interface Checkpoint {
-  history: readonly Content[];
+  /**
+   * The standard history array used for model requests.
+   * Only included in legacy checkpoints (pre-2.0).
+   */
+  history?: readonly Content[];
   authType?: AuthType;
   /**
    * The rich message records which are the source of truth for the session.
@@ -372,34 +377,37 @@ export class Logger {
       // eslint-disable-next-line @typescript-eslint/no-unsafe-assignment
       const parsedContent = JSON.parse(fileContent);
 
-      // Handle legacy format (just an array of Content)
       if (Array.isArray(parsedContent)) {
         // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
         return { history: parsedContent as Content[], messages: [] };
       }
 
-      if (
-        typeof parsedContent === 'object' &&
-        parsedContent !== null &&
-        'history' in parsedContent
-      ) {
+      if (typeof parsedContent === 'object' && parsedContent !== null) {
         // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
-        const checkpoint = parsedContent as Checkpoint;
+        const raw = parsedContent as Record<string, unknown>;
+        if (raw['version'] === '2.0') {
+          // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
+          const msgs = (raw['messages'] as MessageRecord[]) ?? [];
+          return {
+            ...raw,
+            history: reconstructHistory(msgs),
+            messages: msgs,
+          };
+        }
         return {
-          ...checkpoint,
-          messages: checkpoint.messages ?? [],
+          ...raw,
+          // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
+          history: (raw['history'] as Content[]) ?? [],
+          // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
+          messages: (raw['messages'] as MessageRecord[]) ?? [],
         };
       }
 
-      debugLogger.warn(
-        `Checkpoint file at ${path} has an unknown format. Returning empty checkpoint.`,
-      );
       return { history: [], messages: [] };
     } catch (error) {
       // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
       const nodeError = error as NodeJS.ErrnoException;
       if (nodeError.code === 'ENOENT') {
-        // This is okay, it just means the checkpoint doesn't exist in either format.
         return { history: [], messages: [] };
       }
       debugLogger.error(