feat: enhance telemetry with error classification and duration tracking for environment manager registration

Author: eleanorjboyd

src/common/telemetry/constants.ts

@@ -60,7 +60,8 @@ export interface IEventNamePropertyMapping {
 
     /* __GDPR__
         "environment_manager.registered": {
-            "managerId" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "owner": "eleanorjboyd" }
+            "managerId" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "owner": "eleanorjboyd" },
+            "<duration>": { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true, "owner": "eleanorjboyd" }
         }
     */
     [EventNames.ENVIRONMENT_MANAGER_REGISTERED]: {

src/common/telemetry/errorClassifier.ts

@@ -0,0 +1,48 @@
+import { CancellationError } from 'vscode';
+
+export type DiscoveryErrorType =
+    | 'spawn_timeout'
+    | 'spawn_enoent'
+    | 'permission_denied'
+    | 'canceled'
+    | 'parse_error'
+    | 'unknown';
+
+/**
+ * Classifies an error into a telemetry-safe category for the `errorType` property.
+ * Does NOT include raw error messages (PII risk from file paths) — only the category.
+ */
+export function classifyError(ex: unknown): DiscoveryErrorType {
+    if (ex instanceof CancellationError) {
+        return 'canceled';
+    }
+
+    if (!(ex instanceof Error)) {
+        return 'unknown';
+    }
+
+    // Check error code for spawn failures (Node.js sets `code` on spawn errors)
+    const code = (ex as NodeJS.ErrnoException).code;
+    if (code === 'ENOENT') {
+        return 'spawn_enoent';
+    }
+    if (code === 'EACCES' || code === 'EPERM') {
+        return 'permission_denied';
+    }
+
+    // Check message patterns
+    const msg = ex.message.toLowerCase();
+    if (msg.includes('timed out') || msg.includes('timeout')) {
+        return 'spawn_timeout';
+    }
+    if (msg.includes('parse') || msg.includes('unexpected token') || msg.includes('json')) {
+        return 'parse_error';
+    }
+
+    // Check error name for cancellation variants
+    if (ex.name === 'CancellationError' || ex.name === 'AbortError') {
+        return 'canceled';
+    }
+
+    return 'unknown';
+}

src/extension.ts

@@ -547,6 +547,12 @@ export async function activate(context: ExtensionContext): Promise<PythonEnviron
             await sendProjectStructureTelemetry(projectManager, envManagers);
         } catch (error) {
             traceError('Failed to initialize environment managers:', error);
+            sendTelemetryEvent(
+                EventNames.EXTENSION_MANAGER_REGISTRATION_DURATION,
+                start.elapsedTime,
+                undefined,
+                error instanceof Error ? error : undefined,
+            );
             // Show a user-friendly error message
             window.showErrorMessage(
                 l10n.t(

src/features/envManagers.ts

@@ -16,6 +16,7 @@ import {
     PackageManagerAlreadyRegisteredError,
 } from '../common/errors/AlreadyRegisteredError';
 import { traceError, traceVerbose } from '../common/logging';
+import { StopWatch } from '../common/stopWatch';
 import { EventNames } from '../common/telemetry/constants';
 import { sendTelemetryEvent } from '../common/telemetry/sender';
 import { getCallingExtension } from '../common/utils/frameUtils';
@@ -71,6 +72,7 @@ export class PythonEnvironmentManagers implements EnvironmentManagers {
     constructor(private readonly pm: PythonProjectManager) {}
 
     public registerEnvironmentManager(manager: EnvironmentManager): Disposable {
+        const registrationStopWatch = new StopWatch();
         const managerId = generateId(manager.name);
         if (this._environmentManagers.has(managerId)) {
             const ex = new EnvironmentManagerAlreadyRegisteredError(
@@ -105,7 +107,7 @@ export class PythonEnvironmentManagers implements EnvironmentManagers {
         this._onDidChangeEnvironmentManager.fire({ kind: 'registered', manager: mgr });
 
         if (!managerId.toLowerCase().startsWith('undefined_publisher.')) {
-            sendTelemetryEvent(EventNames.ENVIRONMENT_MANAGER_REGISTERED, undefined, {
+            sendTelemetryEvent(EventNames.ENVIRONMENT_MANAGER_REGISTERED, registrationStopWatch.elapsedTime, {
                 managerId,
             });
         }

src/internal.api.ts

@@ -31,6 +31,7 @@ import { CreateEnvironmentNotSupported, RemoveEnvironmentNotSupported } from './
 import { StopWatch } from './common/stopWatch';
 import { EventNames } from './common/telemetry/constants';
 import { sendTelemetryEvent } from './common/telemetry/sender';
+import { classifyError } from './common/telemetry/errorClassifier';
 
 export type EnvironmentManagerScope = undefined | string | Uri | PythonEnvironment;
 export type PackageManagerScope = undefined | string | Uri | PythonEnvironment | Package;
@@ -213,14 +214,14 @@ export class InternalEnvironmentManager implements EnvironmentManager {
                 envCount: envs.length,
             });
         } catch (ex) {
-            const isTimeout = ex instanceof Error && ex.message.includes('timed out');
+            const errorType = classifyError(ex);
             sendTelemetryEvent(
                 EventNames.ENVIRONMENT_DISCOVERY,
                 sw.elapsedTime,
                 {
                     managerId: this.id,
-                    result: isTimeout ? 'timeout' : 'error',
-                    errorType: ex instanceof Error ? ex.name : 'unknown',
+                    result: errorType === 'canceled' || errorType === 'spawn_timeout' ? 'timeout' : 'error',
+                    errorType,
                 },
                 ex instanceof Error ? ex : undefined,
             );