I am green to this whole pfSense thing, but I do like it so far.
That said, I have had to resolve several issues to smooth out the installation of it. Most
were just related to simple config issues - Who knew reading the manual could be a good thing?
But now I am completely stumped.
This installation of pfSense (2.2) is configured with Squid (3.4.10_2 pkg 0.2.6) and Squid_Guard (1.4_7 pkg v.1.9.6). Squid is in transparent mode, and I have created/distributed a certificate for MitM on SSL.
The filtering works great for http and https. Everything is working pretty well, except E-Mail - it is not working, at all.
The email is setup as follows: The company subscribes to Office365. The users use Outlook on their PCs.
When Outlook opens it says, "Trying to connect..." then "Disconnected". It goes back and forth a few times then stops on...