I have an end user, on 1 pc that cannot retrieve mail tips in Outlook.

Outlook 2010, Exchange 2010.

Troubleshoot local issues. Cleaned up cache. Downloaded OAB. Cleared mail tips cache. Tried in and out of cache mode. Tested new mail profile. Tested different user on same machine. Same results. Tested her account on the terminal server and it worked normally.

One thing I came across that is puzzling, she / any user on her pc receives certificate errors (first 2 checks are green, fails 3rd name mismatch). But, the errors reference a wildcard cert for *.bluehost.com, issued by Positive SSL. The Exchange Server uses a standard SSL from Go Daddy. Yet the wildcard cert is somehow referencing mail.domain.org (FQDN for Exchange) as well as autodisover.domain.org. After looking into this I suspect the mailtips are related directly to this cert issue, since autodiscover problems can be a cause (I also do not get cert errors on the terminal server under her or other users). Confirmed that Bluehost hosts their website. 

Additional discovery showed catch all ip configured in external DNS (ping anything.domain.org returns same ip). Logged back on to the user pc. Checked NIC settings to verify there was nothing pointing to external DNS. Confirmed it was set to DHCP. Logged in to the domain controller and verified the scope options in DHCP did not include any external DNS. Flushed / registered DNS. Checked for entries in host file.  Checked local user and computer certificate store and did not see anything out of the norm.

Again, this is affecting any user on that pc, but apparently no other user on any other pc. Short of wiping the user's pc what are some possible options?

Thank in advance!

Bryan

• Edited by bhodges Saturday, February 07, 2015 12:32 AM forgot a detail

if you think it's due to autodiscover error, it's better to post in the Exchange server forum to get more ideas on this issue

https://social.technet.microsoft.com/Forums/office/en-US/home?category=exchangeserver

Discovered a new twist to the scenario today. This location uses Microsoft TMG as a proxy. If I go into Internet Options on the computer having the issue and remove the use proxy option, the certificate error goes away and the Mail Tips start working again. If I enable it again, then both errors return. The perplexing part is all of the other desktops have the proxy setting enabled and do not have the issue. So, again, the problem is isolated to this one client.

Thoughts?