@JohnW66 Just to confirm, are you using WAF with App GW? If so, it is a good idea to increase the idle timeout value if you are facing timeout issues. VMs don't require reboot in this process. Please let us know if you have any further questions/concerns and we will be glad to assist. Thank you!
Here is a document which explains how to troubleshoot some common error with Application Gateway such as Request Timeout.
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