diff --git a/run/core/deployment-orchestrator.ts b/run/core/deployment-orchestrator.ts
index 9354bcd..5153bf8 100644
--- a/run/core/deployment-orchestrator.ts
+++ b/run/core/deployment-orchestrator.ts
@@ -611,12 +611,16 @@ export class DeploymentOrchestrator {
    * 3. Log results and continue even if cleanup fails
    */
   private async cleanupOrphanedPorts(deploymentOrder: string[]): Promise<void> {
+    this.logger.info(`Checking ${deploymentOrder.length} deployments for orphaned ports...`);
     const orphanedPorts: Array<{ port: number; pid: number; serviceId: string }> = [];
 
     // Phase 1: Discover all orphaned ports
     for (const depName of deploymentOrder) {
       const depManifest = this.deploymentRegistry.get(depName);
-      if (!depManifest) continue;
+      if (!depManifest) {
+        this.logger.debug(`[OrphanCleanup] Deployment '${depName}' not found in registry`);
+        continue;
+      }
 
       for (const svc of depManifest.services) {
         if (DOCKER_ONLY_TYPES.has(svc.type)) continue;
@@ -626,17 +630,22 @@ export class DeploymentOrchestrator {
 
         // If we already have a PID file, normal shutdown handled it
         const trackedPid = await readPidFile(serviceId);
-        if (trackedPid !== null) continue;
+        if (trackedPid !== null) {
+          this.logger.debug(`[OrphanCleanup] ${serviceId} has PID file (${trackedPid}), skipping`);
+          continue;
+        }
 
         // Check if an orphaned process is holding this port
         const portPid = await getPortPid(svc.port);
         if (portPid) {
+          this.logger.info(`  → Port ${svc.port} (${serviceId}) held by orphan PID ${portPid}`);
           orphanedPorts.push({ port: svc.port, pid: portPid, serviceId });
         }
       }
     }
 
     if (orphanedPorts.length === 0) {
+      this.logger.debug('[OrphanCleanup] No orphaned processes found');
       return;
     }