I have an exchange 2007 with all service roles installed on 1 windows server 2008 box, and an Edge server on another box. Internally, users are randomly asking for password when opening Outlook 2007. When the credential is prompted, the connection status is HTTPS otherwise it shows as TCP/IP. I even unchecked the CONNECT TO MICROSOFT EXCHANGE USING HTTP in Outlook, but when user re-open Outlook, that setting is checked off again by default. Any suggestions are really appreciated. Thanks in advance.

What is the client authentication set to for Outlook Anywhere? (Get-outlookanywhere) I assume its set to basic. You may want to set to NTLM so users wont get prompted with the Set-outlookanywhere command. That would mask the password prompts but would not change the fact that clients are falling back to OUtlook ANywhere. I assume the defaults are checked to only use HTTP only for slow connections in Outlook.

That is quick Thanks Andy. yes the client authentication is BASIC, and the defaults are checked to only use HTTP only for slow connections in Outlook. So should I set the authentication to NTLM instead as this credential prompted is only affected some users randomly? Thanks again.

That's really your call. If this only affects a few users, you may want to investigate them specfically rather than setting it globally. Another consideration is whether your firewall/ reverse proxy/packet inspecting networking devices support NTLM auth from the outside of your org. If they dont, then remote user will fail if change to NTLM. (Making changes before any holiday is always a bad idea of course!)

(Making changes before any holiday is always a bad idea of course!) You're absolutely right!!! Okay I would leave it the way it is then.... I still don't know why users are randomly got prompted. Any other comments are greatly appreciated. Thanks all.

For those users having issues, new Outlook Profiles may be worth trying- Ensure thet have the latest NIC drivers, etc... Also, uncheck the "use HTTP only for slow connections in Outlook" box ( so both fast and slow use TCP only) and test that out and see how it goes.

as you said internally users re being asked for the password...i wnder why. I'll just re-configure the a new profile for one of those affected users and let is use MAPI, why would it go for Outlook Anyhere since the client is on the LAN. happpy thankgiving.

Vministrator, how would I fix this?

Dear Jon, The issue you reported is probably unnatural. Well, unfoertunity is the other name of Exchange. In such case you may need to properly investigate different related log files, because logs are the ultimate path to find out the challenge.

Thanks Dev Ranjan.