Exchange 5.5 migration across domains

J

jjeff1

Limp Gawd
Joined
Jul 29, 2011
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So I've inherited a bit of a mess. This location originally had several NT4 domains. One of those was a resource domain which contained an exchange 5.5 server. That domain had 1 way trusts so users on the other domains could have mailboxes on the Exchange server. In fact all of the user accounts associated with mailboxes are on the 2008 domains, the resource domain has no user accounts.

Fast forward 10 years, the resource domain was upgraded to windows 2000, but still has an NT4 DC and is in Windows 2000 mixed mode. The other domains were all upgraded to windows 2008 and now are all a single forest.

So I have forest A in 2000 mixed mode with 1 domain, running exchange 5.5. It has 1 way trusts to all the domains in forest B in 2008 native mode.

The goal here is to install Exchange 2007 on to the 2008 forest, move all the mailboxes and settings, then eliminate the 2000 forest and the old exchange 5.5 server.

I know I can use exmerge and move mailboxes over, but I'd really like to keep all the permissions and other settings. I'm struggling to come up with a decent way of doing this.

My first thought was to install the ADC to migrate data from the exchange 5.5 server to the 2008 domains, then install exchange 2003 there and migrate the mailbox data.

Edit: over 900 mailboxes and 140GB of mail. PSTs are probably not an option here.

Anyone have experience with this sort of thing?
 
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Trash it and start fresh. Seriously you will end up doing 6 hours of work to setup new exchange and import the mailboxes instead of spending weeks trying to upgrade 5.5 to 2003 to 2010 just to preserve permissions.
 
I would just recreate the accounts and use .PST files and upload from the clients Outlook back to the server, we had a 5.5 server and moved to gmail and it was a nightmare! In the end the PST was the only way we could really do it.
 
Wow... Just wow...

140GB and 900 boxes on 5.5 with a 1-side NT trust mess for this long? Chuck Norris has nothing on your predecessor for letting that clusterfsck go on that long. Software degradation over time is one thing, but that's a big, nasty pain point to house on, I'm guessing 10+ year old hardware.

I know you mentioned you like to keep permissions, but is the structure that deep? I'd have to agree with the others. Rebuild it right and you won't have to worry at night. The good news is that 5.5 was pre- active directory so you won't have to worry about any dregs of an old exchange setup in your forrest. But to do what you want, you are right, it'll have to be a swing conversion. 5.5 to 2003 (the furthest you can go with 5.5 compatibility) and then 2003 to 2007 as you mentioned. However, be prepared for LOTS of NDRs, and other random mail flow issues. 5.5 to 2003 has never been a pretty conversion without full documentation of the original 5.5 install. If you haven't bought the 2007 licensing yet, just go all the way to 2010 and be done. LOTS of new toys in 2010.
 
Like all of the others had said, just Wow. Shame on the previous Admin for basically doing nothing except keeping old crap going. Trash it all and start new. There is nothing to learn from doing migrations of systems that old to newer ones. Its a waste of your time.
 
Wow...900 mailboxes and that many gigs....how widespread are the users? I'd have a tough time thinking that doing the old manual start from scratch PST approach would be easy with 900 mailboxes.
 
The network covers 8 buildings spread out over a city. The servers were converted to virtual machines a couple years ago, so its not running on old hardware.

As for stringing up the previous IT folks, they were operating under the idea that the product they had worked and was well understood by their staff and end users. Yes, they were aware that Exchange 5.5 was no longer supported.

To be honest, the only stumbling block I have here is that the exchange server is in a trusted domain that's not part of the forest. Were the exchange server in the same forest as the user accounts, an upgrade wouldn't be a problem.
 
I'm not an Exchange guru, but I'd almost want to start fresh with Exchange 2010.

Let us know how it goes.
 
Your users really did more permissions tweaking than sharing out their calendars to secretaries?

I agree with others in this thread and would cut and run from Exchange 5.5. You might have better luck searching info related to do a bulk export.

http://support.microsoft.com/kb/188628

fibroptikl makes a good point, 2010 is the way to go... provided you aren't locked in by a license purchase of 2007 already. We skipped 2007 completely.
 
Update on this, which makes it even worse.

The previous people didn't do a good job with their active directory. Those 3 user domains in the same forest? No, actually they have 3 forests with 1 domain each, and one way trusts between the various domains.
 
So the answer here is that it was no problem.

The IT folks were already in the process of migrating all their user accounts over to a single domain.

Exchange 5.5 is not forest aware, that is, as long as you have a 2way trust bwteeen your exchange server's domain and your user account domain, it works.

The answer here is as follows:

1. move all user accounts to your target forest.
2. setup your exchange ADC and point it from your exchange server (any domain) to your new forest's DCs.
3. install exchange 2003 in new forest
4. move mailboxes
5. decomission exchange 5.5 server.

Oddly enough, the exchange 5.5 OWA worked (at least for a while), even with people on the new server.

I haven't gotten to step 5 yet, still about 100 mailboxes yet to move, but so far there have been only minor issues.

Time expended is roughly 20 hours, probably another 2-4 hours to complete.
 
Wow, curious to see your storage size shrink after the conversion. I feel you pain also went through a similar exercise at my company with 2000 dc's two forests, ad 5.5 level, exchange 2k.... basically everything is running win2k8 2008 level dc's ad level with exchange 2007, took major time here too :)
 
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