PfSense 2.2 - MS Outlook to Office365 via Exhange proxy - disconnected.

[--MySelf-- 0]

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? ;D

This installation of pfSense (2.2) is configured with Squid (3.4.10_2 pkg 0.2.6) and Squid_Guard (1.4_4 pkg v.1.9.6). Squid is in transparent mode, and I have created/distributed a certificate for MitM on SSL.

I am down to one remaining issue, affecting all users of Outlook to send/receive mail via Office365:
When Outlook opens it says, "Trying to connect…" then "Disconnected". It goes back and forth a few times then stops on "Disconnected". As well, there is a security alert which appears:

autodiscover.*****.com
Information you exchange with this site cannot be viewed or changed by others. However, there is a problem with the site's security certificate.
The security certificate is from a trusted certifying authority.
The security certificate date is valid.
The name on the security certificate is invalid or does not match the name of the site.
Do you want to proceed?
[Yes] [No] [View certificate]

Yes/No/View Certificate - no options associated with this dialog have any observable impact.

Due to various searches regarding this topic I have tried:

• Services - Proxy Service - ACLs - "acl safeports" and "acl sslports" – added Ports MS documentation indicates Outlook/Exchange uses.

• Firewall - Aliases - IP – Created alias with "Type"="Hosts", "office365.com" and added reference to alias in Services - Proxy Service - General - Transparent Proxy Settings - "Bypass proxy... destination..."

• Services - Proxy Service - General - "Custom ACLS (Before_Auth)" – added "always_direct allow all" and "ssl_bump server-first all"

I simply do not know what to try next. I do not see a clear example of steps to try/follow.

I really need to get this working and would appreciate any assistance geared towards a first time user of pfSense.