diff --git a/components/ws-manager-bridge/ee/src/bridge.ts b/components/ws-manager-bridge/ee/src/bridge.ts
index 73dfcfcd232c09..d67b48e4759517 100644
--- a/components/ws-manager-bridge/ee/src/bridge.ts
+++ b/components/ws-manager-bridge/ee/src/bridge.ts
@@ -56,6 +56,12 @@ export class WorkspaceManagerBridgeEE extends WorkspaceManagerBridge {
                 return
             }
             span.setTag("updatePrebuiltWorkspace.prebuildId", prebuild.id);
+            span.setTag("updatePrebuiltWorkspace.workspaceInstance.statusVersion", status.statusVersion);
+
+            if (prebuild.statusVersion <= status.statusVersion) {
+                this.prometheusExporter.recordStalePrebuildEvent()
+            }
+            prebuild.statusVersion = status.statusVersion
 
             if (prebuild.state === 'queued') {
                 // We've received an update from ws-man for this workspace, hence it must be running.
diff --git a/components/ws-manager-bridge/src/prometheus-metrics-exporter.ts b/components/ws-manager-bridge/src/prometheus-metrics-exporter.ts
index 6be619e515ef6f..54ad63fa90f0d8 100644
--- a/components/ws-manager-bridge/src/prometheus-metrics-exporter.ts
+++ b/components/ws-manager-bridge/src/prometheus-metrics-exporter.ts
@@ -16,6 +16,7 @@ export class PrometheusMetricsExporter {
     protected readonly clusterScore: prom.Gauge<string>;
     protected readonly clusterCordoned: prom.Gauge<string>;
     protected readonly statusUpdatesTotal: prom.Counter<string>;
+    protected readonly stalePrebuildEventsTotal: prom.Counter<string>;
 
     protected activeClusterNames = new Set<string>();
 
@@ -47,6 +48,10 @@ export class PrometheusMetricsExporter {
             help: 'Total workspace status updates received',
             labelNames: ["workspace_cluster", "known_instance"]
         });
+        this.stalePrebuildEventsTotal = new prom.Counter({
+            name: "gitpod_ws_manager_bridge_stale_prebuild_events_total",
+            help: "Total count of stale prebuild events received by workspace manager bridge"
+        })
     }
 
     observeWorkspaceStartupTime(instance: WorkspaceInstance): void {
@@ -87,5 +92,9 @@ export class PrometheusMetricsExporter {
     statusUpdateReceived(installation: string, knownInstance: boolean): void {
         this.statusUpdatesTotal.labels(installation, knownInstance ? "true" : "false").inc();
     }
+
+    recordStalePrebuildEvent(): void {
+        this.stalePrebuildEventsTotal.inc();
+    }
 }