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2 out of 6 PC's prompting for username and password in Outlook 2007 and 2010 running Exchange 2007

Hi All,

I've just set up a 2008 SBS server for a client, replacing an old 2003 SBS box.  I've set the new server up using the methods I have used countless times in the past, didn't bother to migrate I just backed up emails and data and started afresh with the new server.

All of the 6 PC's are running Windows XP Pro and Outlook 2007 apart trom one which is running Outlook 2010.

I've run all the updates on the server inlcuding SP2 for 2008 and SP3 rollup 9(?) for Exchange.  I've set autodiscover.domain.com in external DNS and have installed a signed UCC cert containing autodiscover and remote.domain and autodiscover works fine as does OWA e.t.c.

Problem is I've got 1 Outlook 2007 PC and 1 Outlook 2010 PC out of the 6 PC's asking for username and password on Outlook launch and every now and then while using Outlook. Cancelling the prompt works for a while and I can continue using Outlook but then it pops back up again.

I've read Demazter's article and have added Kernal Authentication to Windows authentication in ISS to Autodiscover, OAB directories e.t.c. as recommended but  I still keep getting the prompts on 2 PC's and it's driving me crazy!  Really could do with some help please before I go mad.

Many thanks

Adam
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amlydiate
Asked:
amlydiate
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1 Solution
 
smckeown777Commented:
Is the SBS doing DHCP yes?

Can you check the primary DNS server IP on those machines are pointing to the server cause that will sometimes cause prompts to happen...just first thing to look at possibly
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amlydiateAuthor Commented:
Yep DHCP doing its job, it's an SBS server so it's handling everything. Did an ipconfig /all and dg is the router, DNS is the server so all seems fine there.
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smckeown777Commented:
What SP level are those machines, Office I mean? Any difference in the working machines vs the non-working?
Reason I ask is since you have 4 working machines that tells me the issue is pc related, not server...
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Exchange_GeekCommented:
've read Demazter's article and have added Kernal Authentication to Windows authentication in ISS to Autodiscover, OAB directories e.t.c. as recommended but  I still keep getting the prompts on 2 PC's and it's driving me crazy!

So, what is the security on OL set to: NTLM / Negotiate / Kerberos?

More over, what is the Connection Status pointing to when ever you get prompted on these OL clients?

Regards,
Exchange_Geek
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MegaNuk3Commented:
Are the 2 that are prompting in cached mode?
Try turning cached mode off and if it stops prompting then you need have a look at your OAB URL...
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amlydiateAuthor Commented:
Hi,

Have tried Basic and NTLM auth in the settings in Outlook with no difference.

Connection status in Outlook is "Need Password"

Am running updates on one of the PCs now and will report back.

Many thanks

Adam
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amlydiateAuthor Commented:
OK I've tried disabling cached mode and initially there were NO password prompts!  However then I quit Outlook then opened it again and BANG - password request came back again.

Really at my wits end with this. Microsoft have severely dropped the ball with this one.
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smckeown777Commented:
Few things...

1) I assume you've patched Office to match the working machines yes?
2) If yes to the above, can you re-create the mail profile on the client machine?

By re-create I mean, delete the mail settings and start Outlook as if you haven't a profile, it will walk through the wizard to connect to Exchange again, when you created the mail profile the first time did you use the 'Automatic' option or did you have to use the manual option?

What I want to see is when using the wizard it will try to 'auto detect' the mail settings(server/etc) - if there are any issues with mail certs at this point it will complain - and thus we might get to the answer quicker

Or if you did the manual option when you first setup - why? Was auto detect not working?

Try those steps to see where we end up...
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smckeown777Commented:
One last thing...on the client machine can you hold down CTRL key and right click on the Outlook icon in the system tray - on the pop-up that comes up click on the 'Connection Status' - does it show any fails in there?
Also on that right click menu there's a 'Test Email Auto Configuration' - run that and see if anything fails(it will run Autodiscover test which should pass...)

Note as well this is on Outlook 2007 version(not familiar with 2010's options as haven't got a 2010 client at minute)
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MegaNuk3Commented:
Could be a faulty stored credential, Close Outlook and try this:
1.)Go into Control panel--> credentials manager
2.) Save/export/backup the vault
3.) Delete everything in there
4.) Open Outlook
4.) open
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amlydiateAuthor Commented:
Thank you all very much for your suggestions, going away for a weeks holiday but will try all of them when I get back and let you all know.

Thanks again

Adam
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amlydiateAuthor Commented:
I'm afraid none of the above suggestions have done the trick.  Am probably going to try a full reinstall. Many thanks everyone for your helpful suggestions though
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Exchange_GeekCommented:
@amlydiate: Before you work with full re-install.

Here is the final test that you could check to see if the issue is with your machine OR simply user's mailbox profile.

=> Create OL profile of another user on this machine and check for the Password update pop up.
=> Run through netstat -a and see which box is the machine trying to talk to for authentication - port 389/3268.
=> Also, check if there are any network drivers update - a possible reason of popup could be faulty NIC Cards.
=> Re-install of OL won't help if there is a NIC Card issue - remember that.

Regards,
Exchange_Geek
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amlydiateAuthor Commented:
Thank you that did it!!
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