SBS 2011 Exchange – Outlook clients intermittently asking for credentials

exchange-2010outlook-2007outlook-2010windows-sbs-2011

I have an SBS 2011 Standard machine that clients running Microsoft Outlook 2007 and 2010 have issues connecting to – every hour or so they are asked to enter mailbox account credentials.

The server is as follows:

  • Fully patched with Windows Updates
  • After out-of-box install, the Autodiscover record was missing in the DNS (this was added – still same issue)
  • Self signed certificate is being used not a purchased UC subject-alternate-name cert
  • User ticks Remember Password in Outlook, but it still pops up again later anyway
  • User clicks cancel without entering details, and they can still send/receive!
  • Clients and server are all on the same subnet
  • No antivirus or firewall is in place that would block any traffic
  • iPhones installed with the self signed cert work with active sync perfectly fine

Can someone kindly advise:

  1. What the issue may be and how to diagnose further?
  2. If Subject-Alternate-Name certificates are required for SBS or if self-signed is OK
  3. Most importantly, how to enable tracing in Outlook or SBS so I can find out why credentials are being asked

Best Answer

One thing that could be worth checking is if the Exchange Address Book service is running, as it tends to start a bit early with the latest patches for Exchange, and then fail starting up.