diff --git a/packages/cli/src/ui/hooks/useGeminiStream.test.tsx b/packages/cli/src/ui/hooks/useGeminiStream.test.tsx
index 97a442efce..5f4438f09e 100644
--- a/packages/cli/src/ui/hooks/useGeminiStream.test.tsx
+++ b/packages/cli/src/ui/hooks/useGeminiStream.test.tsx
@@ -26,6 +26,7 @@ import {
   TrackedCancelledToolCall,
 } from './useReactToolScheduler.js';
 import {
+  ApprovalMode,
   Config,
   EditorType,
   AuthType,
@@ -194,6 +195,7 @@ describe('useGeminiStream', () => {
       getProjectRoot: vi.fn(() => '/test/dir'),
       getCheckpointingEnabled: vi.fn(() => false),
       getGeminiClient: mockGetGeminiClient,
+      getApprovalMode: () => ApprovalMode.DEFAULT,
       getUsageStatisticsEnabled: () => true,
       getDebugMode: () => false,
       addHistory: vi.fn(),
diff --git a/packages/cli/src/ui/hooks/useGeminiStream.ts b/packages/cli/src/ui/hooks/useGeminiStream.ts
index 0c58fa17b1..aaa54bd121 100644
--- a/packages/cli/src/ui/hooks/useGeminiStream.ts
+++ b/packages/cli/src/ui/hooks/useGeminiStream.ts
@@ -25,6 +25,9 @@ import {
   UnauthorizedError,
   UserPromptEvent,
   DEFAULT_GEMINI_FLASH_MODEL,
+  logConversationFinishedEvent,
+  ConversationFinishedEvent,
+  ApprovalMode,
   parseAndFormatApiError,
 } from '@google/gemini-cli-core';
 import { type Part, type PartListUnion, FinishReason } from '@google/genai';
@@ -172,6 +175,27 @@ export const useGeminiStream = (
     return StreamingState.Idle;
   }, [isResponding, toolCalls]);
 
+  useEffect(() => {
+    if (
+      config.getApprovalMode() === ApprovalMode.YOLO &&
+      streamingState === StreamingState.Idle
+    ) {
+      const lastUserMessageIndex = history.findLastIndex(
+        (item: HistoryItem) => item.type === MessageType.USER,
+      );
+
+      const turnCount =
+        lastUserMessageIndex === -1 ? 0 : history.length - lastUserMessageIndex;
+
+      if (turnCount > 0) {
+        logConversationFinishedEvent(
+          config,
+          new ConversationFinishedEvent(config.getApprovalMode(), turnCount),
+        );
+      }
+    }
+  }, [streamingState, config, history]);
+
   const cancelOngoingRequest = useCallback(() => {
     if (streamingState !== StreamingState.Responding) {
       return;
diff --git a/packages/cli/tsconfig.json b/packages/cli/tsconfig.json
index 46fce70784..44424d671d 100644
--- a/packages/cli/tsconfig.json
+++ b/packages/cli/tsconfig.json
@@ -3,7 +3,7 @@
   "compilerOptions": {
     "outDir": "dist",
     "jsx": "react-jsx",
-    "lib": ["DOM", "DOM.Iterable", "ES2022"],
+    "lib": ["DOM", "DOM.Iterable", "ES2023"],
     "types": ["node", "vitest/globals"]
   },
   "include": [
diff --git a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
index 2a66fa0ca5..9b51b13dab 100644
--- a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
+++ b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
@@ -17,6 +17,7 @@ import {
   SlashCommandEvent,
   MalformedJsonResponseEvent,
   IdeConnectionEvent,
+  ConversationFinishedEvent,
   KittySequenceOverflowEvent,
   ChatCompressionEvent,
   FileOperationEvent,
@@ -47,6 +48,7 @@ export enum EventNames {
   IDE_CONNECTION = 'ide_connection',
   KITTY_SEQUENCE_OVERFLOW = 'kitty_sequence_overflow',
   CHAT_COMPRESSION = 'chat_compression',
+  CONVERSATION_FINISHED = 'conversation_finished',
 }
 
 export interface LogResponse {
@@ -728,6 +730,28 @@ export class ClearcutLogger {
     this.flushIfNeeded();
   }
 
+  logConversationFinishedEvent(event: ConversationFinishedEvent): void {
+    const data: EventValue[] = [
+      {
+        gemini_cli_key: EventMetadataKey.GEMINI_CLI_SESSION_ID,
+        value: this.config?.getSessionId() ?? '',
+      },
+      {
+        gemini_cli_key: EventMetadataKey.GEMINI_CLI_CONVERSATION_TURN_COUNT,
+        value: JSON.stringify(event.turnCount),
+      },
+      {
+        gemini_cli_key: EventMetadataKey.GEMINI_CLI_APPROVAL_MODE,
+        value: event.approvalMode,
+      },
+    ];
+
+    this.enqueueLogEvent(
+      this.createLogEvent(EventNames.CONVERSATION_FINISHED, data),
+    );
+    this.flushIfNeeded();
+  }
+
   logKittySequenceOverflowEvent(event: KittySequenceOverflowEvent): void {
     const data: EventValue[] = [
       {
diff --git a/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts b/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
index 500b472b39..5b7005c70f 100644
--- a/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
+++ b/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
@@ -232,6 +232,16 @@ export enum EventMetadataKey {
   // Logs the length of the kitty sequence that overflowed.
   GEMINI_CLI_KITTY_SEQUENCE_LENGTH = 53,
 
+  // ==========================================================================
+  // Conversation Finished Event Keys
+  // ===========================================================================
+
+  // Logs the approval mode
+  GEMINI_CLI_APPROVAL_MODE = 70,
+
+  // Logs the number of turns
+  GEMINI_CLI_CONVERSATION_TURN_COUNT = 71,
+
   // Logs the number of tokens before context window compression.
   GEMINI_CLI_COMPRESSION_TOKENS_BEFORE = 60,
 
diff --git a/packages/core/src/telemetry/constants.ts b/packages/core/src/telemetry/constants.ts
index 5decd77101..7b9e6f0fea 100644
--- a/packages/core/src/telemetry/constants.ts
+++ b/packages/core/src/telemetry/constants.ts
@@ -16,6 +16,7 @@ export const EVENT_FLASH_FALLBACK = 'gemini_cli.flash_fallback';
 export const EVENT_NEXT_SPEAKER_CHECK = 'gemini_cli.next_speaker_check';
 export const EVENT_SLASH_COMMAND = 'gemini_cli.slash_command';
 export const EVENT_IDE_CONNECTION = 'gemini_cli.ide_connection';
+export const EVENT_CONVERSATION_FINISHED = 'gemini_cli.conversation_finished';
 export const EVENT_CHAT_COMPRESSION = 'gemini_cli.chat_compression';
 export const EVENT_MALFORMED_JSON_RESPONSE =
   'gemini_cli.malformed_json_response';
diff --git a/packages/core/src/telemetry/index.ts b/packages/core/src/telemetry/index.ts
index b0c26046bb..a0b78add88 100644
--- a/packages/core/src/telemetry/index.ts
+++ b/packages/core/src/telemetry/index.ts
@@ -27,6 +27,7 @@ export {
   logApiResponse,
   logFlashFallback,
   logSlashCommand,
+  logConversationFinishedEvent,
   logKittySequenceOverflow,
   logChatCompression,
 } from './loggers.js';
@@ -40,6 +41,7 @@ export {
   ApiResponseEvent,
   TelemetryEvent,
   FlashFallbackEvent,
+  ConversationFinishedEvent,
   KittySequenceOverflowEvent,
   SlashCommandEvent,
   makeSlashCommandEvent,
diff --git a/packages/core/src/telemetry/loggers.ts b/packages/core/src/telemetry/loggers.ts
index dcf29f8fe9..04fd244783 100644
--- a/packages/core/src/telemetry/loggers.ts
+++ b/packages/core/src/telemetry/loggers.ts
@@ -19,6 +19,7 @@ import {
   EVENT_NEXT_SPEAKER_CHECK,
   SERVICE_NAME,
   EVENT_SLASH_COMMAND,
+  EVENT_CONVERSATION_FINISHED,
   EVENT_CHAT_COMPRESSION,
   EVENT_MALFORMED_JSON_RESPONSE,
 } from './constants.js';
@@ -35,6 +36,7 @@ import {
   NextSpeakerCheckEvent,
   LoopDetectedEvent,
   SlashCommandEvent,
+  ConversationFinishedEvent,
   KittySequenceOverflowEvent,
   ChatCompressionEvent,
   MalformedJsonResponseEvent,
@@ -409,6 +411,27 @@ export function logIdeConnection(
   logger.emit(logRecord);
 }
 
+export function logConversationFinishedEvent(
+  config: Config,
+  event: ConversationFinishedEvent,
+): void {
+  ClearcutLogger.getInstance(config)?.logConversationFinishedEvent(event);
+  if (!isTelemetrySdkInitialized()) return;
+
+  const attributes: LogAttributes = {
+    ...getCommonAttributes(config),
+    ...event,
+    'event.name': EVENT_CONVERSATION_FINISHED,
+  };
+
+  const logger = logs.getLogger(SERVICE_NAME);
+  const logRecord: LogRecord = {
+    body: `Conversation finished.`,
+    attributes,
+  };
+  logger.emit(logRecord);
+}
+
 export function logChatCompression(
   config: Config,
   event: ChatCompressionEvent,
diff --git a/packages/core/src/telemetry/types.ts b/packages/core/src/telemetry/types.ts
index 7010e69846..176bbf88da 100644
--- a/packages/core/src/telemetry/types.ts
+++ b/packages/core/src/telemetry/types.ts
@@ -5,7 +5,7 @@
  */
 
 import { GenerateContentResponseUsageMetadata } from '@google/genai';
-import { Config } from '../config/config.js';
+import { ApprovalMode, Config } from '../config/config.js';
 import { CompletedToolCall } from '../core/coreToolScheduler.js';
 import { DiscoveredMCPTool } from '../tools/mcp-tool.js';
 import { DiffStat, FileDiff } from '../tools/tools.js';
@@ -387,6 +387,20 @@ export class IdeConnectionEvent {
   }
 }
 
+export class ConversationFinishedEvent {
+  'event_name': 'conversation_finished';
+  'event.timestamp': string; // ISO 8601;
+  approvalMode: ApprovalMode;
+  turnCount: number;
+
+  constructor(approvalMode: ApprovalMode, turnCount: number) {
+    this['event_name'] = 'conversation_finished';
+    this['event.timestamp'] = new Date().toISOString();
+    this.approvalMode = approvalMode;
+    this.turnCount = turnCount;
+  }
+}
+
 export class KittySequenceOverflowEvent {
   'event.name': 'kitty_sequence_overflow';
   'event.timestamp': string; // ISO 8601
@@ -447,5 +461,6 @@ export type TelemetryEvent =
   | KittySequenceOverflowEvent
   | MalformedJsonResponseEvent
   | IdeConnectionEvent
+  | ConversationFinishedEvent
   | SlashCommandEvent
   | FileOperationEvent;