Problem using Outlook on clients after migrating from 2003 Enterprise to 2003 SBS

I have recently migrated a 2003 Enterprise  server to a 2003 SBS (for legal reasons) and I am having some annoying problems.
I decided to recreate active directory because there were only about 15 users on the system that I wanted to keep.  Each of the users was using roaming profiles so I copied their profiles and shared them on the new server, then I made sure all their accounts point to their profiles - this works fine.  After some buggy roaming profile problems I got everyone's account working well, but I tried to open Outlook on their system and it said "Could not start Microsoft Office Outlook" and closed - this happened on every member of the default group 'users'.  I figured it was a permissions problem so I gave full control to the profiles directory for everyone and id didn't help, so I added them all to the domain admins group and it didn't help, so I made domain admins their default group - boom - works great.

What do you think is wrong with my setup here?  I am a Linux Guru and this 2003 SBS is making me mad!

Thanks in advance!
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
This isn't necessarily a permissions problem, but more likely an overall configuration issue.  The "default group" has no real bearing unless you have Linux Machines (POSIX, actually) or Macs attached to your network.  The fact that making the Domain Admins the Primary Group is probably just patching the problem which has more to do with local machine permissions (users need to have Local Administrator permissions on each machine they use Outlook in order for it to install correctly).

I can provide you with the "fix" for this if you read the steps outlined here:

HOWEVER... I really would worry that you didn't configure your server at all correctly (based on a few comments you made), and you will most certainly continue to run into more problems.  In fact, the fix I listed above may not work at all because there could be a domino effect of making changes to a misconfigured system.

A couple of questions that come to mind...
I'm assuming that you didn't really "migrate" since you say you recreated active directory.  But how did you add the users to your active directory?  Did you use the "Add User" wizard?

How did you add the computers to Active Directory?  Did you use the "Add Computer" wizard?  (If you used the Add User wizard as part of your installation's To-Do list, it would have automatically brought you into the Add Computer wizard).

What kind of email service are you using?  If Exchange, how did you migrate their mailboxes?

Take a look at for the full Getting Started overview.  

FYI, SBS will only make you mad if you don't read the directions first.  This is one product that comes with a user manual that's really necessary to use.  All of it is in the Help & Support section on your server.  This product is designed to be installed and configured in a standard manner... and only after it's up and running nicely should you make any customized changes (roaming profiles are a customization, by the way).

Please don't take any of these comments in any way other than the spirit in which they are given... SBS is often misunderstood --- or in some cases, never understood to begin with. Hopefully, this can be the beginning of something good for you!  :-)

kamermansAuthor Commented:
You are correct in saying that I didn't really "migrate" it - I just set it up on my network and then added the users by hand in Active Directory, then used ExMerge to merge the mailboxs (which seems to work fine).
kamermansAuthor Commented:
I really need to correct this problem and I don't mind manually modifying the permisisons for each user if that's what I have to do.  You mentioned "users need to have Local Administrator permissions on each machine they use Outlook in order for it to install correctly".  What do I have to do to make this happen then?  Can't I do this with GPOs?

Since I just copied the profiles from one server to the other I imagine the permissions are messed up on the profiles, should I make the user the "Owner/Creator" of their respective profile directory?  I'm guessing that the user didn't have access to their own Outlook directory in their profile and that's why it wouldn't start.
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When Jeff said
"users need to have Local Administrator permissions on each machine they use Outlook in order for it to install correctly".  

He was refereing to the security on the PC, (right lick my computer->manage->local users and groups) add the domain users account to the local administrators group.  

Truth be told, If you have the time I agree with Jeff...start will save you a ton of headaches later on.
Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
My first item of concern for you would be that you said, "I just set it up on my network..."
Is your Server 2003 Enterprise Edition still on that network?  Did you transfer all FSMO roles to the SBS?  If you haven't, then I would assume that it's been less than 14 days since you've done this... because at the 14-day point, your SBS will shut down if it's not the Root of the Forest and the holder of all FSMO roles.  See

These would be the full steps to do a Server 2003 to SBS 2003 upgrade:

You need to take care of this immediately if you haven't already done so.

Secondly, you can't add users to an SBS by hand unless you're willing to do ALL that the Add User wizard does.  (Which, of course, doesn't make sense to do by hand then).  

So, let's take a step back then...

You probably want to remove all of your users and then re-add them according to the steps outlined here: 

You will note that this post also references What is important to note is that you must first create the user according to SBS's requirements of using the wizard.  You can THEN assign a roaming profile to that person per the KB article.  Otherwise, you will not have properly added the user to the network and the appropriate security groups required by SBS, and by not using the Add User wizard, your users will not have access to Sharepoint.

ExMerge is absolutely fine to use to migrate mailboxes.


kamermansAuthor Commented:
Ok - I setup the new SBS on a fresh network with no other PDCs, I setup the domain controller using the Server Configuration Wizard and added some administrative users.  Then I took the 2003 Ent. Server off the existing network and installed the new one in it's place.  After reconfguring the clients (due to changes in the DHCP server, etc...), I added all the users that I wanted to have on the system as if they were new.  I then merged their mail accounts which went well.  Now here is where I want some advice - I copied all the profiles from the old server to the new SBS server with the help of an external drive - then I copied them from that drive to the new server and had these outlook issues.

I have tested a theory and made a new user that has never existed, lets call that user 'newuser', I gave newuser a roaming profile and logged in as him on a client.  The user received a nice new profile and when I ran outlook it installed propery and connected to Exchange without a hitch.  So my question naturally was - what was different between his profile and everyone else's - well on the server side, newuser owns his profile and on all the "moved" profiles, obviously 'administrator' owns them.  Could this have been the problem all along?

Thanks for your help,

Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Actually, and please don't take this the wrong way, you needed advice much earlier than the point at which you state above.

>>>> "I setup the domain controller using the Server Configuration Wizard and added some administrative users"
How did you go about aquiring your SBS?  Because the "Configure your Server Wizard" is NOT available on SBS.  This is NOT how it gets installed or configured.  Active Directory is installed in a default configuration as part of the initial installation and should not be modified (at least until you have the server running properly).

kamermansAuthor Commented:
Don't worry - I won't take it the wrong way.  I bought this server from dell (Poweredge SC1420) - I'm not sure if it was the "Configure your server wizard" it was whatever default wizard shows up when you install SBS 2003 - I'm looking at the server right now and I used both the "to do checklist" and the SBS Server Management MMC.

I understand that I needed help before I got to the point that I am at, but I still need this to work correctly, so another thing I was testing is to delete the users profiles (the ones that I copied incorrectly) and logon to the the client that has the profile they want cached locally as the local administrator, then copy theprofile back to the server by going to System Properties -> Advanced -> User Profiles and doing "Copy To" on the correct profile and allowing the correct user to access the files - this has seemed to help.

To clarify - Active Directory was setup with the default configuration as part of the initial installation and has not been modified (with the exception of adding users).

I am running out of time because I need to get the rest of it setup so I have also applied my group policy to the users and added a startup script, and redirected Windows Update to WSUS and this has worked correctly.
Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Okay... much clearer then...

The local administrator profile will AUTOMATICALLY migrate to the domain user's profile if you use the http://servername/connectcomputer method of adding workstations to the network.

I hope you followed the prescribed method to redirect Windows Update to WSUS, because if you didn't, again there will be problems... SBS configuration requires following a different path, most of the time.  

How to for WSUS is here:

Overview of why SBS should be handled differently is here:

To automatically migrate user's local admin profile correctly, you need to remove the workstations from the network and rejoin them.  To do so, please follow these steps:

On each Workstation:
1.  Log in with THAT machine's LOCAL administrator account.
2.  Unjoin the domain into a WORKGROUP
3.  Change the name of the computer
4.  Delete or rename the following directory C:\Program Files\Microsoft Windows Small Business Server\Clients
5.  Reboot

Then on the server, from the Server Management Console:
1.  Remove the client computers if it still shows in the Client Computer screen on the Server Management Console
2.  Add the client with it's NEW name using the Add Computer wizard

Then, go back to the client machine and join the domain by opening Internet Explorer and navigating to http://servername/connectcomputer  -- you will be prompted for which domain user to add and which local profile to associate with that user.  You can then create your roaming profiles as discussed earlier in this thread.


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kamermansAuthor Commented:
Thanks for your help Jeff, I think I can take it from here.  It seems the SBS is much different from Server Std!

Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Yes, it is!  Standard Server 2003 is only just a component of SBS -- among other things.  Be sure to review the ITPro article I've linked above because it gives a good overview of this.

Good Luck!

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