Hi @Eddie Does IT .
Thanks for reaching out to Microsoft Q&A
Reinstalling the connectors is the first troubleshooting step to take when dealing with this type of issue.
Besides that, check the Connector server logs which are basically the Application event viewer ones to search for potential communication issues between the server and Azure. There are more details about that on this document https://learn.microsoft.com/en-us/entra/identity/app-proxy/application-proxy-troubleshoot#connector-errors but feel free to reach out if you have further questions.