diff --git a/bin/omarchy-windows-vm b/bin/omarchy-windows-vm
index 3ef9eb1102..aedc92fd24 100755
--- a/bin/omarchy-windows-vm
+++ b/bin/omarchy-windows-vm
@@ -283,8 +283,7 @@ launch_windows() {
       exit 1
     fi
 
-    # Wait for RDP to be ready
-    echo "Waiting for Windows VM to be ready..."
+    echo "Waiting for RDP to be ready..."
     WAIT_COUNT=0
     while ! nc -z 127.0.0.1 3389 2>/dev/null; do
       sleep 2
@@ -297,8 +296,18 @@ launch_windows() {
       fi
     done
 
-    # Give it a moment more to fully initialize
-    sleep 5
+    echo "Waiting for Windows VM to start..."
+    WAIT_COUNT=0
+    until docker logs omarchy-windows 2>&1 | grep -qi "windows started successfully"; do
+      sleep 2
+      WAIT_COUNT=$((WAIT_COUNT + 1))
+      if [ $WAIT_COUNT -gt 60 ]; then  # 2 minutes timeout
+        echo ""
+        echo "❌ Timeout: Windows VM failed to start within 2 minutes"
+        echo "   Check logs: docker logs omarchy-windows"
+        exit 1
+      fi
+    done
   fi
 
   # Extract credentials from compose file