Squid and Windows Server 2012 R2 Essential Anywhere Access

[BaNZ]

As if anyone uses Microsoft Anywhere access! If they do, then hopefully this will help them.

I've got squid and transparent proxy setup on my pfsense box.

I was testing this out on my home environment for a client. I've setup port forwarding to the MS Server. The port forwarding works and I can see the port is opened. But when verifying the configuration, Anywhere access keeps failing and says port is not opened / configured.

You need to add the IP of the server to the proxy bypass list. Or else you will experience problems.