No notification from Duo; Denied due to no response

We are using Duo for 2FA access to Remote Desktop. Just started experimenting with it for a few users. I have one user for whom Duo Security stops sending notifications to his phone. At that point, his connection is denied due to No Response. For our other users, it’s working fine and continues to work each time. For this user, I first had him re-enroll. That worked for a day or so. Now, I have his account set up on Bypass so that he can get his work done.

What are the troubleshooting steps that I can take? There’s no notification at all, so I can’t really trace what’s happening.

Thanks!

These guides to push troubleshooting would be a good place to start:

Troubleshooting Duo Push notification issues on iOS devices

Troubleshooting Duo Push notification issues on Android devices

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