Refactor IDE client state management, improve user-facing error messages, and add logging of connection events (#5591)

Co-authored-by: matt korwel <[email protected]>

6 files changed, 64 insertions, 3 deletions

diff --git a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
index 6b85a664..649d82b6 100644
--- a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
+++ b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
@@ -21,6 +21,7 @@ import {
   NextSpeakerCheckEvent,
   SlashCommandEvent,
   MalformedJsonResponseEvent,
+  IdeConnectionEvent,
 } from '../types.js';
 import { EventMetadataKey } from './event-metadata-key.js';
 import { Config } from '../../config/config.js';
@@ -44,6 +45,7 @@ const loop_detected_event_name = 'loop_detected';
 const next_speaker_check_event_name = 'next_speaker_check';
 const slash_command_event_name = 'slash_command';
 const malformed_json_response_event_name = 'malformed_json_response';
+const ide_connection_event_name = 'ide_connection';
 
 export interface LogResponse {
   nextRequestWaitMs?: number;
@@ -578,6 +580,18 @@ export class ClearcutLogger {
     this.flushIfNeeded();
   }
 
+  logIdeConnectionEvent(event: IdeConnectionEvent): void {
+    const data = [
+      {
+        gemini_cli_key: EventMetadataKey.GEMINI_CLI_IDE_CONNECTION_TYPE,
+        value: JSON.stringify(event.connection_type),
+      },
+    ];
+
+    this.enqueueLogEvent(this.createLogEvent(ide_connection_event_name, data));
+    this.flushIfNeeded();
+  }
+
   logEndSessionEvent(event: EndSessionEvent): void {
     const data = [
       {
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 0fc35894..54f570f1 100644
--- a/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
+++ b/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
@@ -190,6 +190,13 @@ export enum EventMetadataKey {
 
   // Logs the model that produced the malformed JSON response.
   GEMINI_CLI_MALFORMED_JSON_RESPONSE_MODEL = 45,
+
+  // ==========================================================================
+  // IDE Connection Event Keys
+  // ===========================================================================
+
+  // Logs the type of the IDE connection.
+  GEMINI_CLI_IDE_CONNECTION_TYPE = 46,
 }
 
 export function getEventMetadataKey(
diff --git a/packages/core/src/telemetry/constants.ts b/packages/core/src/telemetry/constants.ts
index 7dd5c8d1..7d840815 100644
--- a/packages/core/src/telemetry/constants.ts
+++ b/packages/core/src/telemetry/constants.ts
@@ -15,6 +15,7 @@ export const EVENT_CLI_CONFIG = 'gemini_cli.config';
 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 METRIC_TOOL_CALL_COUNT = 'gemini_cli.tool.call.count';
 export const METRIC_TOOL_CALL_LATENCY = 'gemini_cli.tool.call.latency';
diff --git a/packages/core/src/telemetry/loggers.ts b/packages/core/src/telemetry/loggers.ts
index 2aa0d86a..e3726ccb 100644
--- a/packages/core/src/telemetry/loggers.ts
+++ b/packages/core/src/telemetry/loggers.ts
@@ -12,6 +12,7 @@ import {
   EVENT_API_REQUEST,
   EVENT_API_RESPONSE,
   EVENT_CLI_CONFIG,
+  EVENT_IDE_CONNECTION,
   EVENT_TOOL_CALL,
   EVENT_USER_PROMPT,
   EVENT_FLASH_FALLBACK,
@@ -23,6 +24,7 @@ import {
   ApiErrorEvent,
   ApiRequestEvent,
   ApiResponseEvent,
+  IdeConnectionEvent,
   StartSessionEvent,
   ToolCallEvent,
   UserPromptEvent,
@@ -355,3 +357,24 @@ export function logSlashCommand(
   };
   logger.emit(logRecord);
 }
+
+export function logIdeConnection(
+  config: Config,
+  event: IdeConnectionEvent,
+): void {
+  ClearcutLogger.getInstance(config)?.logIdeConnectionEvent(event);
+  if (!isTelemetrySdkInitialized()) return;
+
+  const attributes: LogAttributes = {
+    ...getCommonAttributes(config),
+    ...event,
+    'event.name': EVENT_IDE_CONNECTION,
+  };
+
+  const logger = logs.getLogger(SERVICE_NAME);
+  const logRecord: LogRecord = {
+    body: `Ide connection. Type: ${event.connection_type}.`,
+    attributes,
+  };
+  logger.emit(logRecord);
+}
diff --git a/packages/core/src/telemetry/telemetry.test.ts b/packages/core/src/telemetry/telemetry.test.ts
index 8ebb3d9a..9734e382 100644
--- a/packages/core/src/telemetry/telemetry.test.ts
+++ b/packages/core/src/telemetry/telemetry.test.ts
@@ -12,7 +12,6 @@ import {
 } from './sdk.js';
 import { Config } from '../config/config.js';
 import { NodeSDK } from '@opentelemetry/sdk-node';
-import { IdeClient } from '../ide/ide-client.js';
 
 vi.mock('@opentelemetry/sdk-node');
 vi.mock('../config/config.js');
@@ -30,7 +29,6 @@ describe('telemetry', () => {
       targetDir: '/test/dir',
       debugMode: false,
       cwd: '/test/dir',
-      ideClient: IdeClient.getInstance(false),
     });
     vi.spyOn(mockConfig, 'getTelemetryEnabled').mockReturnValue(true);
     vi.spyOn(mockConfig, 'getTelemetryOtlpEndpoint').mockReturnValue(
diff --git a/packages/core/src/telemetry/types.ts b/packages/core/src/telemetry/types.ts
index 9d1fd77a..668421f0 100644
--- a/packages/core/src/telemetry/types.ts
+++ b/packages/core/src/telemetry/types.ts
@@ -308,6 +308,23 @@ export class MalformedJsonResponseEvent {
   }
 }
 
+export enum IdeConnectionType {
+  START = 'start',
+  SESSION = 'session',
+}
+
+export class IdeConnectionEvent {
+  'event.name': 'ide_connection';
+  'event.timestamp': string; // ISO 8601
+  connection_type: IdeConnectionType;
+
+  constructor(connection_type: IdeConnectionType) {
+    this['event.name'] = 'ide_connection';
+    this['event.timestamp'] = new Date().toISOString();
+    this.connection_type = connection_type;
+  }
+}
+
 export type TelemetryEvent =
   | StartSessionEvent
   | EndSessionEvent
@@ -320,4 +337,5 @@ export type TelemetryEvent =
   | LoopDetectedEvent
   | NextSpeakerCheckEvent
   | SlashCommandEvent
-  | MalformedJsonResponseEvent;
+  | MalformedJsonResponseEvent
+  | IdeConnectionEvent;