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Exchange 2003 - Adding new server, some users can't connect to moved mailbox

Hi, I have a customer with a single Exchange 2003 SP2 server running on Windows Server 2003 Enterprise Edition.  That server hardware is non-name-brand and really old.  So, we decided to move the Exchange process over to an HP DL380 server that is basically sitting there bored (just file & print).  I've installed Exchange 2003, SP2, and other available updates.  I moved a test mailbox over from old to new servers and it connected okay.  Outlook started up, found the moved mailbox and came up with no issues.  The Control Panel, Mail app showed the new server name in there for that mailbox after starting up Outlook for the first time.  All seemed great.  So, I moved some mailboxes last night and today a portion of those moved mailboxes have issues.  Outlook starts up and pops up a dialog box that says, "unable to open your default e-mail folders.  The Microsoft Exchange Server computer is not available.  Either there are network problems or the Microsoft Exchange Server computer is down for maintenance."

Some people got in at first, but then the connection went to DISCONNECTED (Outlook lower right corner).  That may have been from me restarting the Exchange services, but some that were working before did not reconnect after the services came back up.

I have moved a couple of the mailboxes back to the old server (takes forever) and they seem to work okay.  The ones that were successful connecting once to the new server (i.e., Outlook profile changed to new server), had to have their Outlook profile manually changed back to old server name.  i.e., moving from old to new, Outlook made the change automatically.  But, moving from new back to old, the Outlook profile change was not done automatically.

Any ideas what may be going on here?  I have another processor and more memory for the DL380 (new) server ordered, but I didn't think it was strictly necessary.  The new server already has more horsepower and memory than the old server did.  Old has 4GB RAM and new has 6GB RAM.  Both have Xeon processors, but old server's processor is much older vintage than new server's.  There is plenty of disk space also.

One other odd thing I noticed.  I log on to the Terminal Services server where I have Outlook for testing with the domain Administrator ID.  There is a user ID "bob" with a mailbox.  Administrator has rights to the bob mailbox and I open Outlook with a profile that opens the bob mailbox.  When I moved the bob mailbox to the new server, Outlook started prompting me for username and password and wouldn't let me open that mailbox unless I entered the bob ID and password.  I tested with my non-admin ID bob2 and logged on as bob2, the user did not get prompted, so I didn't worry about it.  I mention this because maybe the new server is not reading AD correctly or something.

PS, the goal is to get everyone over onto the new server and retire the old server.  Once everyone is moved over, I will go through these procedures to shut down the old server:;en-us;307917

I had another topic open on this.  I will post that link momentarily.

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User generated imageA few more notes.  I am on site now and have been looking at what's really going on.  Most, but not all of the users pointed to the new server are in a disconnected state.  At least one user is connected to new server and functioning fine.

I've moved some users back.  When I did so, they connected fine after I manually changed the server that Outlook points to.  It would NOT change that automatically.

When users pointed at the new server start Outlook, they get a certificate error (attached).  The internal domain name ends in .local, not .com.  I don't know what's doing this or where to fix it.
Also, when I go into Exchange System Manager on the old server and try to bring up the mailboxes on the new server, it tells me the Information Store isn't running.  I have restarted the service (on the new server), but it doesn't help.
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I know you've self-solved this - but nevertheless, I thought I ought to jump in!

That prompt is appearing because Outlook 2007/2010 clients are in use with an Exchange 2003 Server, which doesn't have Autodiscover.

That's not a problem - a fully supported configuration - but the newer Outlook clients will try to seek an Autodiscover connection point regardless that one doesn't exist. The automated strategy for doing this attempts to make connections to, so if that resolves ANYWHERE in DNS (either an internal or external zone) and then connects to any form of web server on a secure connection, you're to see that warning.

To avoid it - check for wildcard / (same as parent folder) records in internal DNS if split DNS is configured, or otherwise, public DNS. Also check for explicit records.

This is, of course, assuming you didn't deploy any Exchange 2007/2010 servers, but your description indicates you didn't!

Matt, thanks for your input.  You're right.  2003 at this shop only.  That error went away with the fix to the new server's A record.  Autodiscover does seem to work with Exchange 2003, by the way.  It must be doing it another way besides the name, though.  Outlook 2007 and 2010 do automatically configure themselves for the 2003 server.  2010 is even better as it reads the right user name (I guess from AD).

Anyway, thanks for your help.  I am going to post a separate question (new points) for the "issue" of my administrator ID opening the bob account (mentioned above) getting prompted for credentials every time...and only bob credentials will do, even though Administrator has rights to the mailbox.  I'm guessing I am missing some authentication or other somewhere.  Maybe you can watch for that question ... I would appreciate your help!

Thanks again.

No problem. Yeah, Outlook is quite clever - when joined to the domain, it is able to read all the properties on the user's account. The Exchange Autodiscover request fails (as 2003 doesn't have it), so it then proceeds to attempt to connect directly to the mailbox server recorded in the logged on user's user properties. So it gives a great illusion that the server is involved, when really, it's the client being clever!

I'll try to locate your other question now.