Proxy.ashx and Certificate Errors to ArcGIS Server

We have an arcgis server that only allows access from essentials via the proxy.ashx we set up.

It's not behind a firewall proxy. Though I did have to modify the proxy.ashx to accept a certificate error.

I don't get a certificate error when visiting the arcgis server rest end point when using IE or Chrome on the Essentials server.

We do use a proxy.cs with the server bypassed. But even if I get rid of the proxy.cs and web.config changes altogether it still doesn't connect.

Any direction anyone can point me? Logs aren't showing anything? Any changes that can be made to ignore certificate errors?

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