diff --git a/images/macos/provision/core/open_windows_check.sh b/images/macos/provision/core/open_windows_check.sh
index 1392e0654..002c254bd 100644
--- a/images/macos/provision/core/open_windows_check.sh
+++ b/images/macos/provision/core/open_windows_check.sh
@@ -1,6 +1,16 @@
 #!/bin/bash -e -o pipefail
 
-openwindows=$(osascript -e 'tell application "System Events" to get every window of (every process whose class of windows contains window)')
+retry=10
+while [ $retry -gt 0 ]; do
+    openwindows=$(osascript -e 'tell application "System Events" to get every window of (every process whose class of windows contains window)') && break
+
+    retry=$((retry-1))
+    if [ $retry -eq 0 ]; then
+        echo "No retry attempts left"
+        exit 1
+    fi
+    sleep 30
+done
 IFS=',' read -r -a windowslist <<< "$openwindows"
 
 if [ -n "${openwindows}" ]; then