Remote Outlook Clients Can't access email Always Asking for Password and never connects

Exchange Server 2010 SP3 RU8 64 bit Enterprise
Windows 7 Clients
Outlook 2010

A few days ago all remote clients unable to access email using Outlook 2010 they all are getting Password prompt window.
Enter valid password tries to conect re prompted for password over and over again
checked AD no passwords accounts locked

The same account works on their iPhone iPad, Tablets
The same accounts work with OWA

So active sync is working correct?

This happened after I restarted the exchange server after windows server 2008 updates

Need assistance

Thanks in advance

LVL 23
Thomas GrassiSystems AdministratorAsked:
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Zacharia KurianAdministrator- Data Center & NetworkCommented:
Requires a few more details. To do so try testing your exchange using Microsoft Remote Connectivity Analyzer, from the below link;

Also check your SSL cert in your exchange 2010 server.
Thomas GrassiSystems AdministratorAuthor Commented:
Zacharia Kurian

Ran Microsoft Remote Connectivity Analyzer

This is what I am getting

Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.

How do I fix this?
Thomas GrassiSystems AdministratorAuthor Commented:

Found this

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Thomas GrassiSystems AdministratorAuthor Commented:


I applied the KB931125 still no luck
Zacharia KurianAdministrator- Data Center & NetworkCommented:
1): You have to  cross check if  Outlook anywhere is properly configured/any modifications are done to it.Please follow the below link to cross check the outlook anywhere.

2): Also can you make sure that you SSL certificate is not expired and it contains  the below names. (the URL used for Outlook Web Access)
servername.domainname.local (the internal FQDN of your Exchange Server)
SERVERNAME (NETBIOS Name of your Server)

3:) can you try log in to https://your owa web/rpc (example:, with one of the problematic user, and see if he gets authenticated.

4:) Also make sure that the users are allowed to log on to all computers (can be found in the AD account properties of the user).

5:) Are there any event logs that relates to the issue in your exchange server? if so post them please.
Simon Butler (Sembee)ConsultantCommented:
Do you have Windows 2003 domain controllers?
If so, then there is an update which was released last week which is causing this behaviour.
If you have KB3002657 on the domain controllers (Windows 2003 only) remove it and reboot.


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Thomas GrassiSystems AdministratorAuthor Commented:

Yes 2 windows 2003 Domain Controllers

When i get back on site I will look for that update

Can you point me to the documentation on that?

It is a strange thing this started last week after I applied updates to all server and computers

Hope that is all been puling my hair out here on this one
Simon Butler (Sembee)ConsultantCommented:
The update was released last week - so it would only have happened after making the change.
The update has been pulled now, it was in the overnight security bulletin releases.

The closest you will get to an acknowledgement is on the security bulletin:

Thomas GrassiSystems AdministratorAuthor Commented:


I will research this asap
Thomas GrassiSystems AdministratorAuthor Commented:

Yes KB3002657 & KB3033395  are installed on both my DC's


Microsoft just released another KB3002657 & KB3033395
My WSUS server downloaded them today and both my DC's want to install them

What do you think is best method.

1. Install lasted updates that replaces the fix?

2. what you said earlier uninstall KB3002657  and restart

I this was that serious of an issue then MS must have fixed this problem with the latest I received today

Simon Butler (Sembee)ConsultantCommented:
The two updates are supposed to have resolved the issue, so you can try installing them to see if they do.
I don't have any Windows 2003 DCs with the later versions of Exchange to test myself, so it isn't something I have seen.

Thomas GrassiSystems AdministratorAuthor Commented:
Ok tonight I will apply them and se what happens

I the mean time I have another question open if you have time could you take a look at

Thomas GrassiSystems AdministratorAuthor Commented:

After applying the same updates that Microsoft put out today My remote users now can access the Email Servers Remotely

To All others keep this update in Mind causes bad things to happen

To All others thanks for pitching in to help

All are greatly appreciated.
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