Exchange 2007 - Outlook prompting users to enter password

  • Thread starter Roberto Serrano
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Roberto Serrano

Need some help here. I have 3 exchange servers. I had an issue on 1 about 2 weeks ago and needed a reboot. I applied the latest Microsoft security patches and now everyone on that server gets prompted for their password when they open up outlook. The other 2 are fine. It looks like it may have been one of the updates, don"t know. Does anyone know for sure what would be causing this? If it"s an update, what update is it and how can remove it? Any help would be appreciated


Ed Crowley [MVP]

These computers are domain members and the users are logged on to their computers with their domain accounts, right?Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Roberto Serrano

Correct. Anyone on the other exchange servers can open outlook and it connects fine. Anyone on the 3rd exchange server are prompted for a password everytime they open up outlook.

Ed Crowley [MVP]

What versions of Outlook and how are they connecting (Outlook Anywhere, cached mode)? If there are multiple Outlook versions, does this happen with some versions and not others?Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Le Pivert

What is the service pack level on the problem server?

Is that the same level as the other servers?

"Security patch" would not include a Roll-Up (RU), correct? These are just "plain old" security patches that were installed?

What is the OS on the mail server? Windows 2003? Windows 2008? In Windows 2008, you can look in "View Update History" (option toward the top left in "Windows Updates") and see which updates were installed, by date among other criteria.

Once you determine which ones were installed just before the problem started (assuming one of these is, in fact, the cause), you might try removing them and proceed by trial and error until you resolve the problem, however, removing an application or an update does not always eliminate its consequences so I would, personally, wait for a second opinion on that option (remove and proceed by trial and error).
Does the password prompt go away once the user enters it, or does it reappear at regular intervals?

Once Outlook is open, does it reappear if you run "Send/Receive", either "All" or "This Mailbox"?

Roberto Serrano

Sorry for my lack of details. Exchange 2007 - Each server is at Rollup 9 SP1 and have been like that for a while. Same OS on all 3, Win2k3 R2. All clients are using Outlook 2007.

It only prompts them when they first open up outlook. It stays connected but when you close and re-open, it prompts for the password again. I've had one user complain that it happens multiple times without closing outlook but I moved my account to that server and it just prompts once and then connects when you enter the password

The server in question only received plain old security patches, nothing more that's why I suspect it had to be one of those updates

Ed Crowley [MVP]

Are these clients connecting with Outlook Anywhere? Hold the Ctrl button, click the Outlook icon in the systme tray, select Connection Status... You should see connections via TCP. If you're seeing HTTPS, a password pop-up is normal.

Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Roberto Serrano

The connection is TCP\IP. This was working fine before. I think it has to be one of the updates, just not sure which one. The other 2 servers are not prompting users for there password



Can you check on the Exchange server weather windows authentication flag is enabled on security settings of EWS virtual directory under IIS.



Roberto Serrano

It was enabled. All 3 exchange servers are setup the same. This issue just recently started on my 3rd exchange server after running some updates or that's my conclusion. No one complained untill about a week after I ran the latest patches on that server. I did not run the updates on the other 2 so that's why I'm believing it has to be one of the updates.

Another thing I noticed is that now the Auto Discover feature won't work properly when it trys to find a user on that exchange server. I have to point it to the 1st 2 exchange servers for the user name to resolve.
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