diff --git a/src/vs/base/node/stats.ts b/src/vs/base/node/stats.ts
index ae76a9de2182ff08d51ae75cfaba3690661b25bd..aedbd13349e7dc989eb8e7eafd2481911f5666f7 100644
--- a/src/vs/base/node/stats.ts
+++ b/src/vs/base/node/stats.ts
@@ -17,6 +17,7 @@ export interface WorkspaceStats {
 	configFiles: WorkspaceStatItem[];
 	fileCount: number;
 	maxFilesReached: boolean;
+	launchConfigFiles: WorkspaceStatItem[];
 }
 
 function asSortedItems(map: Map<string, number>): WorkspaceStatItem[] {
@@ -66,7 +67,7 @@ export function collectLaunchConfigs(folder: string): Promise<WorkspaceStatItem[
 	});
 }
 
-export function collectWorkspaceStats(folder: string, filter: string[]): Promise<WorkspaceStats> {
+export async function collectWorkspaceStats(folder: string, filter: string[]): Promise<WorkspaceStats> {
 	const configFilePatterns = [
 		{ 'tag': 'grunt.js', 'pattern': /^gruntfile\.js$/i },
 		{ 'tag': 'gulp.js', 'pattern': /^gulpfile\.js$/i },
@@ -182,15 +183,17 @@ export function collectWorkspaceStats(folder: string, filter: string[]): Promise
 	let token: { count: number, maxReached: boolean } = { count: 0, maxReached: false };
 
 	return new Promise((resolve, reject) => {
-		walk(folder, filter, token, (files) => {
+		walk(folder, filter, token, async (files) => {
 			files.forEach(acceptFile);
 
+			let launchConfigs = await collectLaunchConfigs(folder);
+
 			resolve({
 				configFiles: asSortedItems(configFiles),
 				fileTypes: asSortedItems(fileTypes),
 				fileCount: token.count,
-				maxFilesReached: token.maxReached
-
+				maxFilesReached: token.maxReached,
+				launchConfigFiles: launchConfigs
 			});
 		});
 	});
diff --git a/src/vs/platform/diagnostics/electron-main/diagnosticsService.ts b/src/vs/platform/diagnostics/electron-main/diagnosticsService.ts
index 94cba280d743c2fefbdc54cf175b148fe01bd8a9..9e60ec11d55b6fca551d743d4c895e435f7d265e 100644
--- a/src/vs/platform/diagnostics/electron-main/diagnosticsService.ts
+++ b/src/vs/platform/diagnostics/electron-main/diagnosticsService.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { WorkspaceStats, collectWorkspaceStats, collectLaunchConfigs, WorkspaceStatItem } from 'vs/base/node/stats';
+import { WorkspaceStats, collectWorkspaceStats, WorkspaceStatItem } from 'vs/base/node/stats';
 import { IMainProcessInfo } from 'vs/platform/launch/electron-main/launchService';
 import { ProcessItem, listProcesses } from 'vs/base/node/ps';
 import product from 'vs/platform/node/product';
@@ -110,9 +110,8 @@ export class DiagnosticsService implements IDiagnosticsService {
 								workspaceInfoMessages.push(`|    Folder (${basename(folder)}): ${countMessage}`);
 								workspaceInfoMessages.push(this.formatWorkspaceStats(stats));
 
-								const launchConfigs = await collectLaunchConfigs(folder);
-								if (launchConfigs.length > 0) {
-									workspaceInfoMessages.push(this.formatLaunchConfigs(launchConfigs));
+								if (stats.launchConfigFiles.length > 0) {
+									workspaceInfoMessages.push(this.formatLaunchConfigs(stats.launchConfigFiles));
 								}
 							}));
 						} else {
@@ -196,11 +195,9 @@ export class DiagnosticsService implements IDiagnosticsService {
 								console.log(`|    Folder (${basename(folder)}): ${countMessage}`);
 								console.log(this.formatWorkspaceStats(stats));
 
-								await collectLaunchConfigs(folder).then(launchConfigs => {
-									if (launchConfigs.length > 0) {
-										console.log(this.formatLaunchConfigs(launchConfigs));
-									}
-								});
+								if (stats.launchConfigFiles.length > 0) {
+									console.log(this.formatLaunchConfigs(stats.launchConfigFiles));
+								}
 							}).catch(error => {
 								console.log(`|      Error: Unable to collect workspace stats for folder ${folder} (${error.toString()})`);
 							}));
diff --git a/src/vs/workbench/parts/stats/node/workspaceStats.ts b/src/vs/workbench/parts/stats/node/workspaceStats.ts
index bed2040b45630c7b888422b516348f5c4a040c82..633ba9c3df914442ecbcb51b593d684ab5e4b8a0 100644
--- a/src/vs/workbench/parts/stats/node/workspaceStats.ts
+++ b/src/vs/workbench/parts/stats/node/workspaceStats.ts
@@ -20,6 +20,7 @@ import { extname, join } from 'path';
 import { WORKSPACE_EXTENSION } from 'vs/platform/workspaces/common/workspaces';
 import { IQuickInputService, IQuickPickItem } from 'vs/platform/quickinput/common/quickInput';
 import { IStorageService, StorageScope } from 'vs/platform/storage/common/storage';
+import { collectWorkspaceStats, WorkspaceStats as WorkspaceStatsType } from 'vs/base/node/stats';
 
 const SshProtocolMatcher = /^([^@:]+@)?([^:]+):/;
 const SshUrlMatcher = /^([^@:]+@)?([^:]+):(.+)$/;
@@ -225,10 +226,15 @@ export class WorkspaceStats implements IWorkbenchContribution {
 
 	private report(): void {
 
-		// Workspace Stats
+		// Workspace Tags
 		this.resolveWorkspaceTags(this.windowService.getConfiguration(), rootFiles => this.handleWorkspaceFiles(rootFiles))
 			.then(tags => this.reportWorkspaceTags(tags), error => onUnexpectedError(error));
 
+		// Workspace file types, config files, and launch configs
+		this.getWorkspaceMetadata().then(stats => {
+			this.reportWorkspaceMetadata(stats);
+		});
+
 		// Cloud Stats
 		this.reportCloudStats();
 
@@ -731,4 +737,39 @@ export class WorkspaceStats implements IWorkbenchContribution {
 				this.telemetryService.publicLog('resolveProxy.stats', { type });
 			}).then(undefined, onUnexpectedError);
 	}
+
+	/* __GDPR__
+		"workspace.metadata" : {
+			"fileTypes" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"configTypes" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"launchConfigs" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true }
+		}
+	*/
+	private reportWorkspaceMetadata(stats: WorkspaceStatsType[]): void {
+		for (let stat of stats) { // one event for each root folder in the workspace
+			this.telemetryService.publicLog('workspce.metadata', {
+				'fileTypes': stat.fileTypes,
+				'configTypes': stat.configFiles,
+				'launchConfigs': stat.launchConfigFiles
+			});
+		}
+	}
+
+	private getWorkspaceMetadata(): Promise<WorkspaceStatsType[]> {
+		const workspaceStatPromises: Promise<WorkspaceStatsType>[] = [];
+		const workspace = this.contextService.getWorkspace();
+		workspace.folders.forEach(folder => {
+			const folderUri = URI.revive(folder.uri);
+			if (folderUri.scheme === 'file') {
+				const folder = folderUri.fsPath;
+				workspaceStatPromises.push(collectWorkspaceStats(folder, ['node_modules', '.git']).then(async stats => {
+					return stats;
+				}));
+			}
+		});
+
+		return Promise.all(workspaceStatPromises).then((stats) => {
+			return stats;
+		});
+	}
 }