Outlook 2007 constant username prompt on lan, but for remote exchange

Have a customer who called me today stating they got a new pc with Windows 7 Pro and Outlook 2007. They attempted to setup themselves and apparently ran the install certificate wizard for there remote.server.com workspace (new feature of SBS 2008) since they had did that before for workstations OUTSIDE the network. The problem now is they have connected to the SBS 2008 exchange server but get prompted for username\password for remote.server.com (states this in header of username/pass box) when they open outlook. They can bypass and use the email just a real annoyance to them. We tried entering the domainname\user with no go as well as numerous other options I've found on web with no luck. Anyone have any ideas how have the user reauthenticate with the exchange server on the internal LAN (server.domain.local versus remote.domain.com).

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Scotts1976Author Commented:
Just wanted to update you both with what I found out. I tried practally everything I could think of from following the certificate removal instructions, to creating new user profiles, and even wiping rebuilding the pc in question. Nothing worked so finally yelled loud enough to Dell support to get someone to finally help me and found the actual issue was a Exchange roll up patch which I had no clue about. Apparently it, along with all the latest updates for Microsoft Office 2007, are required before they will work together properly.


Thanks for help. Will split points.
Syed Mutahir AliTechnology ConsultantCommented:
Start > Run > mmc

Click yes to continue

MMC Window Opens up ;

Click on "File" then " Add Remove Snap in"

On the Add or Remove Snap-ins Screen, Select "Certificates" Click "Add"

Select "Computer Account", Click Next, Click Finish, Click OK

Now expand the "Certificates (local Computer)

Expand "Trusted Root Certification Authorities"

Click on "Certificates"

Find the certificate you added "remote.domain.com" and delete it

if you don't find remote.domain.com certificate then look for a certificate with the server name-ca and delete that too.

After deleting that, open up outlook again and see if it prompts you again ;

Also, if the machine is already joined to the domain (connect wizard - http://connect) ; then you can simply create a new profile for the user of that machine and it should be ok.

If you can logon to that machine and see if that machine is joined to the SBS domain and re-create a exchange account profile on it to verify ;

Also, is this the only computer facing this issue or are all computers having this issue ?
Syed Mutahir AliTechnology ConsultantCommented:
If none of the above helps you, i would suggest is to delete all the certificates related to your SBS name and domain name on the client machine from the above steps I mentioned ;

The un-join the machine and re-join using the "http://connect" wizard and create the outlook profile again and it should be ok

I haven't come across this myself so just trying to help

Hope that works for you
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Scotts1976Author Commented:
Thanks for they great info. I will try it out as soon as I can and let you know.

Also to answer your message above this is the only workstation that I know of that is having issue.
Syed Mutahir AliTechnology ConsultantCommented:
I had thought about it initially, its the exchange update rollup 9 which fixes this, but I thought that if it was that it would have appeared to everyone, my bad - I should have mentioned that too when I posted.
Glad it has sorted out for you, have a good new year ahead.
Thanks for the points
Had the same issue but could not fix with anything I could find, this was what fixed it for me.

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