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Outlook Password Prompt Cycle

Outlook 2007/2010 (mail clients)
Windows Server 2003 (DC)
Windows Server 2007 (exchange server) with IIS 6.0

When a user tries to connect with Outlook remotely, they are prompted for their password. After entering their password, The password dialog box returns even though they entered their password correctly.

Internal users do not seem to have this problem, It is just the remote users. They connect to the Exchange Server via VPN or Outlook Anywhere. Web Access works fine so is not a password issue.

The only thing I recall adding recently is the "internet authentication service" on the DC but i have since removed that windows feature but the password issue is still persisting.

Any guidance would be appreciated.
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1 Solution
jnsimexAuthor Commented:
ok, it seem to work when I disable "connect using SSL only" in the Outlook Anywhere settings.

I noticed in the password prompt that server name is now the local server and not the public mail server name.

How can I get it to Outlook to work using SSL?
Will SzymkowskiSenior Solution ArchitectCommented:
This really depends on how you are connecting Outlook to Exchange. If you are using VPN then everything should be fine and you theorectically should not be prompted for crednetials, Make sure that your Outlook Security is set to Negotiate Authentication. This will try and the username and password you used to login to your laptop. If it cannot use this password or the password has been changed, it will prompt for credentials.

If you are using Outlook Anywhere then you are going to need a cert that has the following...

You can also test this externally using the https://testconnectivity.microsoft.com/ and performing the Outlook Connectivity Tests.

jnsimexAuthor Commented:
Hi Will,

Outlook anywhere has worked in the past but not for the last couple of days.

I have ran the Outlook Connectivity test and it passed successfully. I did get 1 warning: Testing the SSL certificate to make sure it's valid but other than that, it was all green.
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jnsimexAuthor Commented:
I gave in and gave MS Support a call and the problem was caused by following update: https://support.microsoft.com/en-us/kb/3002657.

Remove the update from DCs and Exchange server and problem should be fixed.

They refunded the $300 per incident call since they caused the issue.
jnsimexAuthor Commented:
I've requested that this question be closed as follows:

Accepted answer: 0 points for jnsimex's comment #a40662456

for the following reason:

This is the fix as per Microsoft
jnsimexAuthor Commented:
please give Will the points since he replied
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