Hi @wspyy
It is impossible to find the cause of the problem just based on the 500 error message, you can try to generate Failed request tracing and get the detail where you failed.
troubleshooting-failed-requests-using-tracing-in-iis
Besides, check the IIS logs on both the IIS and ARR server to see on which one the 500 is happening.
And you can follow the below article to create reverse proxy: reverse-proxy-with-url-rewrite-v2-and-application-request-routing
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