I am slightly confused (ok very confused), I have an application to sync my Outlook calendar to Googles (we don�t have Exchange so no EAS). When I try to sync at work I get a SSL error.

An error occurred while sending the request>
[(SecureChannelFailure) The request was aborted: Could not create SSL/TLS secure channel.]

I temporarily disabled my Windows (Windows 10 64 bit) firewall and my Antivirus (this was recommended by the application support engineer) and the sync still fails.

I can however connect using a wifi hotspot and the application works properly.

I can also get the application to work using Fiddler and enabling decryption of https port traffic.

The application is supposed to use (you need an account to see links) on port 443, while testing I had no issue getting to any secure sites.

Does anybody have any idea where this application could be being blocked and how Fiddler is able to allow the application to work properly?