diff --git a/src/vs/platform/diagnostics/common/diagnostics.ts b/src/vs/platform/diagnostics/common/diagnostics.ts
index 9adfc578f64..31a4ee17474 100644
--- a/src/vs/platform/diagnostics/common/diagnostics.ts
+++ b/src/vs/platform/diagnostics/common/diagnostics.ts
@@ -63,6 +63,7 @@ export interface PerformanceInfo {
 
 export interface IWorkspaceInformation extends IWorkspace {
 	telemetryId: string | undefined;
+	rendererSessionId: string;
 }
 
 export function isRemoteDiagnosticError(x: any): x is IRemoteDiagnosticError {
diff --git a/src/vs/platform/diagnostics/node/diagnosticsService.ts b/src/vs/platform/diagnostics/node/diagnosticsService.ts
index 43dd25b6a5f..ebc6892cbc9 100644
--- a/src/vs/platform/diagnostics/node/diagnosticsService.ts
+++ b/src/vs/platform/diagnostics/node/diagnosticsService.ts
@@ -539,22 +539,39 @@ export class DiagnosticsService implements IDiagnosticsService {
 				collectWorkspaceStats(folder, ['node_modules', '.git']).then(stats => {
 					type WorkspaceStatsClassification = {
 						'workspace.id': { classification: 'SystemMetaData', purpose: 'FeatureInsight' };
-						fileTypes: { classification: 'SystemMetaData', purpose: 'FeatureInsight', isMeasurement: true };
+						rendererSessionId: { classification: 'SystemMetaData', purpose: 'FeatureInsight' };
 						configTypes: { classification: 'SystemMetaData', purpose: 'FeatureInsight', isMeasurement: true };
 						launchConfigs: { classification: 'SystemMetaData', purpose: 'FeatureInsight', isMeasurement: true };
 					};
 					type WorkspaceStatsEvent = {
 						'workspace.id': string | undefined;
-						fileTypes: WorkspaceStatItem[];
+						rendererSessionId: string;
 						configTypes: WorkspaceStatItem[];
 						launchConfigs: WorkspaceStatItem[];
 					};
 					this.telemetryService.publicLog2<WorkspaceStatsEvent, WorkspaceStatsClassification>('workspace.stats', {
 						'workspace.id': workspace.telemetryId,
-						fileTypes: stats.fileTypes,
+						rendererSessionId: workspace.rendererSessionId,
 						configTypes: stats.configFiles,
 						launchConfigs: stats.launchConfigFiles
 					});
+					stats.fileTypes.forEach(e => {
+						type WorkspaceStatsFileClassification = {
+							rendererSessionId: { classification: 'SystemMetaData', purpose: 'FeatureInsight' };
+							fileType: { classification: 'SystemMetaData', purpose: 'FeatureInsight', isMeasurement: true };
+							fileCount: { classification: 'SystemMetaData', purpose: 'FeatureInsight', isMeasurement: true };
+						};
+						type WorkspaceStatsFileEvent = {
+							rendererSessionId: string;
+							fileType: string;
+							fileCount: number;
+						};
+						this.telemetryService.publicLog2<WorkspaceStatsFileEvent, WorkspaceStatsFileClassification>('workspace.stats.file', {
+							rendererSessionId: workspace.rendererSessionId,
+							fileType: e.name,
+							fileCount: e.count
+						});
+					});
 				}).catch(_ => {
 					// Report nothing if collecting metadata fails.
 				});
diff --git a/src/vs/workbench/contrib/stats/electron-browser/workspaceStats.ts b/src/vs/workbench/contrib/stats/electron-browser/workspaceStats.ts
index f4f8c3bc578..91dbe7c6d76 100644
--- a/src/vs/workbench/contrib/stats/electron-browser/workspaceStats.ts
+++ b/src/vs/workbench/contrib/stats/electron-browser/workspaceStats.ts
@@ -164,16 +164,18 @@ export class WorkspaceStats implements IWorkbenchContribution {
 		this.reportProxyStats();
 
 		const diagnosticsChannel = this.sharedProcessService.getChannel('diagnostics');
-		diagnosticsChannel.call('reportWorkspaceStats', this.getWorkspaceInformation());
+		this.getWorkspaceInformation().then(stats => diagnosticsChannel.call('reportWorkspaceStats', stats));
 	}
 
-	private getWorkspaceInformation(): IWorkspaceInformation {
+	private async getWorkspaceInformation(): Promise<IWorkspaceInformation> {
 		const workspace = this.contextService.getWorkspace();
 		const state = this.contextService.getWorkbenchState();
-		const id = this.workspaceStatsService.getTelemetryWorkspaceId(workspace, state);
+		const telemetryId = this.workspaceStatsService.getTelemetryWorkspaceId(workspace, state);
+		const rendererSessionId = (await this.telemetryService.getTelemetryInfo()).sessionId;
 		return {
 			id: workspace.id,
-			telemetryId: id,
+			telemetryId,
+			rendererSessionId,
 			folders: workspace.folders,
 			configuration: workspace.configuration
 		};