feat: instrument startup telemetry

Author: EhabY

src/core/cliManager.ts

@@ -13,6 +13,8 @@ import { errToStr } from "../api/api-helper";
 import * as pgp from "../pgp";
 import { withCancellableProgress, withOptionalProgress } from "../progress";
 import { isKeyringEnabled } from "../settings/cli";
+import { type CallerMeasurements } from "../telemetry/event";
+import { type TelemetryService } from "../telemetry/service";
 import { tempFilePath, toSafeHost } from "../util";
 import { vscodeProposed } from "../vscodeProposed";
 
@@ -33,13 +35,16 @@ type ResolvedBinary =
 	| { binPath: string; stat: Stats; source: "file-path" | "directory" }
 	| { binPath: string; source: "not-found" };
 
+type CliDownloadReason = "missing" | "version_mismatch";
+
 export class CliManager {
 	private readonly binaryLock: BinaryLock;
 
 	constructor(
 		private readonly output: Logger,
 		private readonly pathResolver: PathResolver,
 		private readonly cliCredentialManager: CliCredentialManager,
+		private readonly telemetry: TelemetryService,
 	) {
 		this.binaryLock = new BinaryLock(output);
 	}
@@ -140,6 +145,8 @@ export class CliManager {
 		);
 
 		let existingVersion: string | null = null;
+		const downloadReason: CliDownloadReason =
+			resolved.source === "not-found" ? "missing" : "version_mismatch";
 		if (resolved.source !== "not-found") {
 			this.output.debug(
 				"Existing binary size is",
@@ -224,13 +231,25 @@ export class CliManager {
 				latestVersion = latestParsedVersion;
 			}
 
-			await this.performBinaryDownload(
-				restClient,
-				latestVersion,
-				downloadBinPath,
-				progressLogPath,
+			const downloadMeasurements: CallerMeasurements = {};
+			return await this.telemetry.trace(
+				"cli.download",
+				async () => {
+					await this.performBinaryDownload(
+						restClient,
+						latestVersion,
+						downloadBinPath,
+						progressLogPath,
+					);
+					const downloadedStat = await cliUtils.stat(downloadBinPath);
+					if (downloadedStat) {
+						downloadMeasurements.sizeBytes = downloadedStat.size;
+					}
+					return this.renameToFinalPath(resolved, downloadBinPath);
+				},
+				{ reason: downloadReason },
+				downloadMeasurements,
 			);
-			return await this.renameToFinalPath(resolved, downloadBinPath);
 		} catch (error) {
 			const fallback = await this.handleAnyBinaryFailure(
 				error,
@@ -480,17 +499,19 @@ export class CliManager {
 							"Skipping binary signature verification due to settings",
 						);
 					} else {
-						await this.verifyBinarySignatures(client, tempFile, [
-							// A signature placed at the same level as the binary.  It must be
-							// named exactly the same with an appended `.asc` (such as
-							// coder-windows-amd64.exe.asc or coder-linux-amd64.asc).
-							binSource + ".asc",
-							// The releases.coder.com bucket does not include the leading "v",
-							// and unlike what we get from buildinfo it uses a truncated version
-							// with only major.minor.patch.  The signature name follows the same
-							// rule as above.
-							`https://releases.coder.com/coder-cli/${parsedVersion.major}.${parsedVersion.minor}.${parsedVersion.patch}/${binName}.asc`,
-						]);
+						await this.telemetry.trace("cli.verify", () =>
+							this.verifyBinarySignatures(client, tempFile, [
+								// A signature placed at the same level as the binary.  It must be
+								// named exactly the same with an appended `.asc` (such as
+								// coder-windows-amd64.exe.asc or coder-linux-amd64.asc).
+								binSource + ".asc",
+								// The releases.coder.com bucket does not include the leading "v",
+								// and unlike what we get from buildinfo it uses a truncated version
+								// with only major.minor.patch.  The signature name follows the same
+								// rule as above.
+								`https://releases.coder.com/coder-cli/${parsedVersion.major}.${parsedVersion.minor}.${parsedVersion.patch}/${binName}.asc`,
+							]),
+						);
 					}
 
 					// Replace existing binary (handles both renames + Windows lock)

src/core/container.ts

@@ -51,6 +51,25 @@ export class ServiceContainer implements vscode.Disposable {
 			context.globalState,
 			this.logger,
 		);
+
+		const sessionId = newSessionId();
+		const localJsonlSink = LocalJsonlSink.start(
+			{
+				baseDir: this.pathResolver.getTelemetryPath(),
+				sessionId,
+			},
+			this.logger,
+		);
+		const session = buildSession(
+			extractExtensionVersion(context.extension.packageJSON),
+			sessionId,
+		);
+		this.telemetryService = new TelemetryService(
+			session,
+			[localJsonlSink],
+			this.logger,
+		);
+
 		// Circular ref: cliCredentialManager ↔ cliManager. The resolver
 		// closure captures `this` by reference, so `this.cliManager` is
 		// available when the closure is called (after construction).
@@ -75,6 +94,7 @@ export class ServiceContainer implements vscode.Disposable {
 			this.logger,
 			this.pathResolver,
 			this.cliCredentialManager,
+			this.telemetryService,
 		);
 		this.contextManager = new ContextManager(context);
 		this.oauthCallback = new OAuthCallback(context.secrets, this.logger);
@@ -96,23 +116,6 @@ export class ServiceContainer implements vscode.Disposable {
 			this.logger,
 		);
 
-		const sessionId = newSessionId();
-		const localJsonlSink = LocalJsonlSink.start(
-			{
-				baseDir: this.pathResolver.getTelemetryPath(),
-				sessionId,
-			},
-			this.logger,
-		);
-		const session = buildSession(
-			extractExtensionVersion(context.extension.packageJSON),
-			sessionId,
-		);
-		this.telemetryService = new TelemetryService(
-			session,
-			[localJsonlSink],
-			this.logger,
-		);
 		this.commandManager = new CommandManager(this.telemetryService);
 	}
 

src/extension.ts

@@ -17,6 +17,7 @@ import { getErrorDetail, toError } from "./error/errorUtils";
 import { OAuthSessionManager } from "./oauth/sessionManager";
 import { Remote } from "./remote/remote";
 import { getRemoteSshExtension } from "./remote/sshExtension";
+import { ActivationTelemetry } from "./telemetry/startup";
 import { registerUriHandler } from "./uri/uriHandler";
 import { initVscodeProposed } from "./vscodeProposed";
 import { ChatPanelProvider } from "./webviews/chat/chatPanelProvider";
@@ -30,6 +31,22 @@ const MY_WORKSPACES_TREE_ID = "myWorkspaces";
 const ALL_WORKSPACES_TREE_ID = "allWorkspaces";
 
 export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
+	const serviceContainer = new ServiceContainer(ctx);
+	ctx.subscriptions.push(serviceContainer);
+	const activationTelemetry = new ActivationTelemetry(
+		serviceContainer.getTelemetryService(),
+	);
+
+	await activationTelemetry.trace(() =>
+		doActivate(ctx, serviceContainer, activationTelemetry),
+	);
+}
+
+async function doActivate(
+	ctx: vscode.ExtensionContext,
+	serviceContainer: ServiceContainer,
+	activationTelemetry: ActivationTelemetry,
+): Promise<void> {
 	// The Remote SSH extension's proposed APIs are used to override the SSH host
 	// name in VS Code itself. It's visually unappealing having a lengthy name!
 	//
@@ -39,6 +56,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	// Cursor and VSCode are covered by ms remote, and the only other is windsurf for now
 	// Means that vscodium is not supported by this for now
 
+	activationTelemetry.setPhase("remote_ssh_extension");
 	const remoteSshExtension = getRemoteSshExtension();
 
 	let vscodeProposed: typeof vscode = vscode;
@@ -57,24 +75,31 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	}
 
 	// Initialize the global vscodeProposed module for use throughout the extension
+	activationTelemetry.setPhase("proposed_api_init");
 	initVscodeProposed(vscodeProposed);
 
-	const serviceContainer = new ServiceContainer(ctx);
-	ctx.subscriptions.push(serviceContainer);
-
 	const output = serviceContainer.getLogger();
 	const mementoManager = serviceContainer.getMementoManager();
 	const secretsManager = serviceContainer.getSecretsManager();
 	const contextManager = serviceContainer.getContextManager();
 	const commandManager = serviceContainer.getCommandManager();
 
 	// Migrate auth storage from old flat format to new label-based format
+	activationTelemetry.setPhase("auth_migration");
 	await migrateAuthStorage(serviceContainer);
 
 	// Clear and capture the startup mode before anything else.
+	activationTelemetry.setPhase("startup_mode");
 	const startupMode = await mementoManager.getAndClearStartupMode();
 
+	activationTelemetry.setPhase("deployment_read");
 	const deployment = await secretsManager.getCurrentDeployment();
+	const deploymentSessionAuth = deployment
+		? await secretsManager.getSessionAuth(deployment.safeHostname)
+		: undefined;
+	activationTelemetry.setAuthState(
+		deploymentSessionAuth ? "valid_token" : "none",
+	);
 
 	// Shared handler for auth failures (used by interceptor + session manager)
 	const handleAuthFailure = (): Promise<void> => {
@@ -99,6 +124,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	};
 
 	// Create OAuth session manager - callback handles background refresh failures
+	activationTelemetry.setPhase("oauth_session");
 	const oauthSessionManager = OAuthSessionManager.create(
 		deployment,
 		serviceContainer,
@@ -109,10 +135,10 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	// This client tracks the current login and will be used through the life of
 	// the plugin to poll workspaces for the current login, as well as being used
 	// in commands that operate on the current login.
+	activationTelemetry.setPhase("client_setup");
 	const client = CoderApi.create(
 		deployment?.url || "",
-		(await secretsManager.getSessionAuth(deployment?.safeHostname ?? ""))
-			?.token,
+		deploymentSessionAuth?.token,
 		output,
 	);
 	ctx.subscriptions.push(client);
@@ -132,6 +158,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 
 	const isAuthenticated = () => contextManager.get("coder.authenticated");
 
+	activationTelemetry.setPhase("tree_views");
 	const myWorkspacesProvider = new WorkspaceProvider(
 		WorkspaceQuery.Mine,
 		client,
@@ -178,6 +205,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	);
 
 	// Create deployment manager to centralize deployment state management
+	activationTelemetry.setPhase("deployment_manager");
 	const deploymentManager = DeploymentManager.create(
 		serviceContainer,
 		client,
@@ -188,6 +216,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 
 	// Register globally available commands.  Many of these have visibility
 	// controlled by contexts, see `when` in the package.json.
+	activationTelemetry.setPhase("commands");
 	const commands = new Commands(serviceContainer, client, deploymentManager);
 
 	// Placeholder tree view for the coderTasks container when not authenticated.
@@ -363,6 +392,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	// (this would require the user to uninstall the Coder extension and
 	// reinstall after installing the remote SSH extension, which is annoying)
 	if (remoteSshExtension && vscodeProposed.env.remoteAuthority) {
+		activationTelemetry.setPhase("remote_setup");
 		try {
 			const details = await remote.setup(
 				vscodeProposed.env.remoteAuthority,
@@ -372,11 +402,14 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 			if (details) {
 				ctx.subscriptions.push(details);
 
-				await deploymentManager.setDeploymentIfValid({
+				const deploymentSet = await deploymentManager.setDeploymentIfValid({
 					safeHostname: details.safeHostname,
 					url: details.url,
 					token: details.token,
 				});
+				activationTelemetry.setAuthState(
+					deploymentSet ? "valid_token" : "expired",
+				);
 
 				// If a deep link stored a chat agent ID before the
 				// remote-authority reload, open it now that the
@@ -391,7 +424,9 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 		} catch (ex) {
 			if (ex instanceof CertificateError) {
 				output.warn(ex.detail);
-				await ex.showNotification("Failed to open workspace", { modal: true });
+				await ex.showNotification("Failed to open workspace", {
+					modal: true,
+				});
 			} else if (isAxiosError(ex)) {
 				const msg = getErrorMessage(ex, "None");
 				const detail = getErrorDetail(ex) || "None";
@@ -422,6 +457,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 			}
 			// Always close remote session when we fail to open a workspace.
 			await remote.closeRemote();
+			activationTelemetry.complete();
 			return;
 		}
 	}
@@ -431,10 +467,12 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 	if (deploymentManager.getCurrentDeployment()) {
 		contextManager.set("coder.loaded", true);
 	} else if (deployment) {
+		activationTelemetry.setPhase("deployment_init");
 		output.info(`Initializing deployment: ${deployment.url}`);
-		deploymentManager
-			.setDeploymentIfValid(deployment)
-			// Failure is logged internally
+		activationTelemetry
+			.traceDeploymentInit(() =>
+				deploymentManager.setDeploymentIfValid(deployment),
+			)
 			.then((success) => {
 				if (success) {
 					output.info("Deployment authenticated and set");
@@ -467,6 +505,7 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
 			}
 		}
 	}
+	activationTelemetry.complete();
 }
 
 /**