I have a client running sbs 2008 for the past 8 months without issues. About a month ago they started getting the password prompt on their outlook 2007 client. I had already installed the update rollup 9 for exchange when the server was first set up and there was no issues with the password prompt. I am using a self-signed cert on the sbs server.
I have done the following in an attempt to fix it without success:
- created a new self-signed certificate
- ran the fix network wizard with no issues
- rant the interent connection wizard
- installed exchange 2007 sp3 and any updates
- disabled the connect via http in outlook
- disabled outook anywhere
- setup A recored for autodiscover.vbis.ca
- tried adding 127.0.0.1 autodiscover.vbis.ca to the local hosts file
- tried disabling the loopback test in registry
- enable kernel-mode authentication on
When I run the outlook test email autoconfiguration I get a security alert about the cerificate name being invalid or not matching the name of the site. The autodiscover failes on all it's checks.