diff --git a/python-packages/gdbrunner/__init__.py b/python-packages/gdbrunner/__init__.py
index 2eabf99d2..e28f34d44 100644
--- a/python-packages/gdbrunner/__init__.py
+++ b/python-packages/gdbrunner/__init__.py
@@ -171,6 +171,10 @@ def start_gdbserver(device, gdbserver_local_path, gdbserver_remote_path,
     # Push gdbserver to the target.
     if gdbserver_local_path is not None:
         device.push(gdbserver_local_path, chroot + gdbserver_remote_path)
+        # If the user here is potentially on Windows, adb cannot inspect execute
+        # permissions. Since we don't know where the users are, chmod
+        # gdbserver_remote_path on device regardless.
+        device.shell(["chmod", "+x", gdbserver_remote_path])
 
     # Run gdbserver.
     gdbserver_cmd = [gdbserver_remote_path]