diff --git a/src/extension.ts b/src/extension.ts
index da65afe9..eccd33ab 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -27,27 +27,33 @@ const DOCUMENT_SELECTOR = [
 
 export async function activate(context: vscode.ExtensionContext) {
     telemetryHelper.setTelemetry('isActivationEvent', 'true');
+    logger.log('Activating extension...', 'ExtensionActivation');
+
     await telemetryHelper.callWithTelemetryAndErrorHandling('azurePipelines.activate', async () => {
         await activateYmlContributor(context);
     });
 
     context.subscriptions.push(telemetryHelper);
 
-    logger.log('Extension has been activated!', 'ExtensionActivated');
+    logger.log('Extension has been activated!', 'ExtensionActivation');
     return schemaContributor;
 }
 
 async function activateYmlContributor(context: vscode.ExtensionContext) {
     const serverOptions: languageclient.ServerOptions = getServerOptions(context);
     const clientOptions: languageclient.LanguageClientOptions = getClientOptions();
-    const client = new languageclient.LanguageClient(LANGUAGE_IDENTIFIER, 'Azure Pipelines Language', serverOptions, clientOptions);
+    const client = new languageclient.LanguageClient(LANGUAGE_IDENTIFIER, 'Azure Pipelines Language Server', serverOptions, clientOptions);
 
     const disposable = client.start();
     context.subscriptions.push(disposable);
 
+    logger.log('Waiting for server to start...', 'ExtensionActivation');
+
     // If this throws, the telemetry event in activate() will catch & log it
     await client.onReady();
 
+    logger.log('Server started', 'ExtensionActivation');
+
     // Fired whenever the server is about to validate a YAML file (e.g. on content change),
     // and allows us to return a custom schema to use for validation.
     client.onRequest(CUSTOM_SCHEMA_REQUEST, (resource: string) => {
@@ -75,6 +81,7 @@ async function activateYmlContributor(context: vscode.ExtensionContext) {
 
     // Load the schema if we were activated because an Azure Pipelines file.
     if (vscode.window.activeTextEditor?.document.languageId === LANGUAGE_IDENTIFIER) {
+        logger.log('Active file is Azure Pipelines, loading schema', 'ExtensionActivation');
         await loadSchema(context, client);
     }
 
@@ -119,18 +126,25 @@ async function loadSchema(
     context: vscode.ExtensionContext,
     client: languageclient.LanguageClient,
     workspaceFolder?: vscode.WorkspaceFolder): Promise<void> {
+    logger.log('Loading schema...', 'LoadSchema');
     if (workspaceFolder === undefined) {
+        logger.log('Detecting workspace folder', 'LoadSchema');
         const textDocument = vscode.window.activeTextEditor?.document;
         if (textDocument?.languageId !== LANGUAGE_IDENTIFIER) {
+            logger.log('Active file not Azure Pipelines', 'LoadSchema');
             return;
         }
 
         workspaceFolder = vscode.workspace.getWorkspaceFolder(textDocument.uri);
     }
 
+    logger.log(`Using workspace folder '${workspaceFolder?.name}'`, 'LoadSchema');
     const schemaFilePath = await locateSchemaFile(context, workspaceFolder);
     const schema = getSchemaAssociation(schemaFilePath);
+
+    logger.log(`Sending schema '${schemaFilePath}' to server`, 'LoadSchema');
     client.sendNotification(SchemaAssociationNotification.type, schema);
+    logger.log('Sent schema to server', 'LoadSchema');
 }
 
 function getServerOptions(context: vscode.ExtensionContext): languageclient.ServerOptions {
diff --git a/src/logger.ts b/src/logger.ts
index 56fda5ad..6fdcddf2 100644
--- a/src/logger.ts
+++ b/src/logger.ts
@@ -18,4 +18,5 @@ export function log(message: string, event?: string): void {
 
     logMessage += message;
     outputChannel.appendLine(logMessage);
+    console.log(logMessage);
 }
diff --git a/src/schema-association-service.ts b/src/schema-association-service.ts
index b0382c79..1a027ce5 100644
--- a/src/schema-association-service.ts
+++ b/src/schema-association-service.ts
@@ -55,11 +55,11 @@ export async function locateSchemaFile(
     // TODO: Support auto-detection for Azure Pipelines files outside of the workspace.
     if (workspaceFolder !== undefined) {
         try {
-            logger.log(`Detecting schema for workspace folder ${workspaceFolder.name}`, 'SchemaDetection');
+            logger.log(`Detecting schema for workspace folder '${workspaceFolder.name}'`, 'SchemaDetection');
             schemaUri = await autoDetectSchema(context, workspaceFolder);
             if (schemaUri) {
                 logger.log(
-                    `Detected schema for workspace folder ${workspaceFolder.name}: ${schemaUri.path}`,
+                    `Detected schema for workspace folder '${workspaceFolder.name}': ${schemaUri.path}`,
                     'SchemaDetection');
                 return schemaUri.path;
             }
@@ -67,7 +67,7 @@ export async function locateSchemaFile(
             // Well, we tried our best. Fall back to the predetermined schema paths.
             // TODO: Re-throw error once we're more confident in the schema detection.
             logger.log(
-                `Error auto-detecting schema for workspace folder ${workspaceFolder.name}: ${String(error)}`,
+                `Error auto-detecting schema for workspace folder '${workspaceFolder.name}': ${String(error)}`,
                 'SchemaDetection');
         }
     }
@@ -89,7 +89,7 @@ export async function locateSchemaFile(
     }
 
     logger.log(
-        `Using hardcoded schema for workspace folder ${workspaceFolder?.name ?? 'ANONYMOUS_WORKSPACE'}: ${schemaUri.path}`,
+        `Using hardcoded schema for workspace folder '${workspaceFolder?.name ?? 'ANONYMOUS_WORKSPACE'}': ${schemaUri.path}`,
         'SchemaDetection');
 
     // TODO: We should update getSchemaAssociations so we don't need to constantly
@@ -347,7 +347,7 @@ async function autoDetectSchema(
 export async function getAzureDevOpsSession(context: vscode.ExtensionContext, options?: vscode.AuthenticationGetSessionOptions): Promise<vscode.AuthenticationSession | undefined> {
     const rawTenantId = vscode.workspace.getConfiguration('azure-pipelines').get<string>('tenant', '');
     const tenantId = rawTenantId.trim().length > 0 ? rawTenantId : undefined;
-    logger.log(`Getting session for tenant ${tenantId ?? 'default'}`, 'SchemaDetection');
+    logger.log(`Getting session for tenant '${tenantId ?? 'default'}'`, 'SchemaDetection');
     const azureDevOpsSession = await vscode.authentication.getSession(
         'microsoft',
         tenantId ? [...AZURE_DEVOPS_SCOPES, `VSCODE_TENANT:${tenantId}`] : AZURE_DEVOPS_SCOPES,