diff --git a/src/sql/workbench/services/contextualization/common/serverContextualizationService.ts b/src/sql/workbench/services/contextualization/common/serverContextualizationService.ts
index 098aa35756..a7f9a9a8f0 100644
--- a/src/sql/workbench/services/contextualization/common/serverContextualizationService.ts
+++ b/src/sql/workbench/services/contextualization/common/serverContextualizationService.ts
@@ -11,6 +11,7 @@ import { IServerContextualizationService } from 'sql/workbench/services/contextu
 import { Disposable } from 'vs/base/common/lifecycle';
 import { ICommandService } from 'vs/platform/commands/common/commands';
 import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { ILogService } from 'vs/platform/log/common/log';
 import { IExtensionService } from 'vs/workbench/services/extensions/common/extensions';
 
 export class ServerContextualizationService extends Disposable implements IServerContextualizationService {
@@ -21,7 +22,8 @@ export class ServerContextualizationService extends Disposable implements IServe
 		@IConnectionManagementService private readonly _connectionManagementService: IConnectionManagementService,
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
 		@IExtensionService private readonly _extensionService: IExtensionService,
-		@ICommandService private readonly _commandService: ICommandService
+		@ICommandService private readonly _commandService: ICommandService,
+		@ILogService private readonly _logService: ILogService
 	) {
 		super();
 	}
@@ -50,9 +52,11 @@ export class ServerContextualizationService extends Disposable implements IServe
 	public getProvider(providerId: string): azdata.contextualization.ServerContextualizationProvider {
 		const provider = this._providers.get(providerId);
 		if (provider) {
+			this._logService.info(`Found server contextualization provider for ${providerId}`);
 			return provider;
 		}
 
+		this._logService.info(`No server contextualization provider found for ${providerId}`);
 		throw invalidProvider(providerId);
 	}
 
@@ -65,18 +69,28 @@ export class ServerContextualizationService extends Disposable implements IServe
 		// Don't need to take any actions if contextualization is not enabled and can return
 		const isContextualizationNeeded = await this.isContextualizationNeeded();
 		if (!isContextualizationNeeded) {
+			this._logService.info('Contextualization is not needed because the GitHub Copilot extension is not installed and/or contextualization is disabled.');
 			return;
 		}
 
 		const getServerContextualizationResult = await this.getServerContextualization(uri);
 		if (getServerContextualizationResult.context) {
+			this._logService.info(`Server contextualization was previously generated for the URI (${uri}) connection, so sending that to Copilot for context.`);
+
 			await this.sendServerContextualizationToCopilot(getServerContextualizationResult.context);
 		}
 		else {
+			this._logService.info(`Server contextualization was not previously generated for the URI (${uri}) connection. Generating now...`);
+
 			const generateServerContextualizationResult = await this.generateServerContextualization(uri);
 			if (generateServerContextualizationResult.context) {
+				this._logService.info(`Server contextualization was generated for the URI (${uri}) connection, so sending that to Copilot.`);
+
 				await this.sendServerContextualizationToCopilot(generateServerContextualizationResult.context);
 			}
+			else {
+				this._logService.warn(`Server contextualization was not generated for the URI (${uri}) connection, so no context will be sent to Copilot.`);
+			}
 		}
 	}
 
@@ -88,9 +102,13 @@ export class ServerContextualizationService extends Disposable implements IServe
 		const providerName = this._connectionManagementService.getProviderIdFromUri(ownerUri);
 		const handler = this.getProvider(providerName);
 		if (handler) {
+			this._logService.info(`Generating server contextualization for ${ownerUri}`);
+
 			return await handler.generateServerContextualization(ownerUri);
 		}
 		else {
+			this._logService.info(`No server contextualization provider found for ${ownerUri}`);
+
 			return Promise.resolve({
 				context: undefined
 			});
@@ -105,9 +123,13 @@ export class ServerContextualizationService extends Disposable implements IServe
 		const providerName = this._connectionManagementService.getProviderIdFromUri(ownerUri);
 		const handler = this.getProvider(providerName);
 		if (handler) {
+			this._logService.info(`Getting server contextualization for ${ownerUri}`);
+
 			return await handler.getServerContextualization(ownerUri);
 		}
 		else {
+			this._logService.info(`No server contextualization provider found for ${ownerUri}`);
+
 			return Promise.resolve({
 				context: undefined
 			});
@@ -120,6 +142,8 @@ export class ServerContextualizationService extends Disposable implements IServe
 	 */
 	private async sendServerContextualizationToCopilot(serverContext: string | undefined): Promise<void> {
 		if (serverContext) {
+			this._logService.info('Sending server contextualization to Copilot');
+
 			// LEWISSANCHEZ TODO: Find way to set context on untitled query editor files. Need to save first for Copilot status to say "Has Context"
 			await this._commandService.executeCommand('github.copilot.provideContext', '**/*.sql', {
 				value: serverContext
@@ -134,7 +158,14 @@ export class ServerContextualizationService extends Disposable implements IServe
 	 */
 	private async isContextualizationNeeded(): Promise<boolean> {
 		const copilotExt = await this._extensionService.getExtension('github.copilot');
+		if (!copilotExt) {
+			this._logService.info('GitHub Copilot extension is not installed, so contextualization is not needed.');
+		}
+
 		const isContextualizationEnabled = this._configurationService.getValue<IQueryEditorConfiguration>('queryEditor').githubCopilotContextualizationEnabled
+		if (!isContextualizationEnabled) {
+			this._logService.info('GitHub Copilot contextualization is disabled, so contextualization is not needed.');
+		}
 
 		return (copilotExt && isContextualizationEnabled);
 	}