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

Tom
LVL 23
Thomas GrassiSystems AdministratorAsked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

x
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

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;

https://testconnectivity.microsoft.com/

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:
Guys

Found this http://support.microsoft.com/en-us/kb/931125

Think this will help?
Determine the Perfect Price for Your IT Services

Do you wonder if your IT business is truly profitable or if you should raise your prices? Learn how to calculate your overhead burden with our free interactive tool and use it to determine the right price for your IT services. Download your free eBook now!

Thomas GrassiSystems AdministratorAuthor Commented:
Guys

Update

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.

http://exchangeserverpro.com/how-to-configure-exchange-server-2010-outlook-anywhere/

2): Also can you make sure that you SSL certificate is not expired and it contains  the below names.

autodiscover.domainname.com
owa.domainname.com (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: https://email.contoso.com/rpc), 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.

Simon.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
Thomas GrassiSystems AdministratorAuthor Commented:
Simon

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:
https://technet.microsoft.com/library/security/ms15-027

Simon.
Thomas GrassiSystems AdministratorAuthor Commented:
Simon

Great

I will research this asap
Thomas GrassiSystems AdministratorAuthor Commented:
Simon

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

Update

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

Thoughts
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.

Simon.
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

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_28636014.html

Cheers
Thomas GrassiSystems AdministratorAuthor Commented:
Simon

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.
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Email Clients

From novice to tech pro — start learning today.