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Replacing a 2008 SBS Server with new 2011 SBS Server - Avoiding Exchange problems

Posted on 2013-06-16
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Last Modified: 2013-06-17
Hi all,

We have a client running 2008 SBS on an old HP Server which is rather underpowered.  The current domain has about 22 users with Exchange mailboxes.

Traditionally when I replace a server like this I tend to prefer to start again with a who,e new domain so that we have a clean slate approach and have always avoided the migration route. What I usually do is export each clients email to a pst file, copy that and the profile folder into a new profile in the new 2011 domain then import the email into the new Exchange via Outlook.

On a couple of occasions though I have experienced a problem which caused issues when users tried to reply to old emails sent from an user on the old domain (they get the bounce back referencing FYDIBOHF23SPDLT.  I never really found a simple or effective cure for that issue (was told to manually add x500 address for each user) and ended up just telling users to start new messages to colleagues rather than replying to old ones.

What I would like advice on is how can I avoid this problem occurring this time round without having to manually add x500 addresses for 22 users?

Many thanks

Adam
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Question by:amlydiate
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Cris Hanna earned 250 total points
ID: 39252782
If the internal server and domain name remains the same in both instances, as well as the fully qualified domain name, you shouldn't see a problem.  This is usually a problem going from SBS 2003 to a newer version, not 2008.  Worst case, they could forward the mail using the GAL look up to the internal recipient
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Author Comment

by:amlydiate
ID: 39252861
Thank for that, so would it be recommended to keep the exact same domain name on the new server as the old one? Would that not cause issues elsewhere?

Thanks

Adam
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Expert Comment

by:Cris Hanna
ID: 39252873
No, if you're doing a clean install they can't be on the same network at the same time anyway
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Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 250 total points
ID: 39253049
You are talking about the X.500 address issue.
It is discussed in this blog posting: http://semb.ee/x500

For this number of users it is easily resolved.

Simon.
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Author Comment

by:amlydiate
ID: 39253115
Hi Sembee,

I'm afraid I followed that guide last time and it still doesn't work on the previous clients who experienced this issue.  I was hoping that there could be something I can do to stop it from happening at all rather than have to manually correct it after....

Thanks

Adam
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LVL 35

Expert Comment

by:Cris Hanna
ID: 39253431
If you notice, that blog is 2003 to 2008 migrations...not 2008 to 2011 and references Exmerge
Exmerge is only available for Exchange 2003 and earlier
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Author Comment

by:amlydiate
ID: 39253445
So, would still appreciate any advice on if/how I can get round this issue when replacing a 2008 SBS server with a brand new 2011 SBS Server without having to manually create X500 records for 25 odd users.

Thanks

Adam
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LVL 35

Expert Comment

by:Cris Hanna
ID: 39253459
So you've done other SBS 2008 to SBS 2011 migrations where this has been an issue, because it shouldn't be.   SBS 2008 doesn't use the .local address anymore, like 2003 did.  So unless you change user names/email addresses with the new install, etc.  you should be just fine
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Author Comment

by:amlydiate
ID: 39253532
I had a client who was running 2003 SBS and I migrated their emails via PST export Import onto a 2008 SBS Server which I then a couple of years later did the same thing to migrate from 2008 to 2011 and it was at that point I got the problem...

My current client however didn't have a server before their 2008 SBS one so I'm gueesing as long as email addresses and usernames remain the same on the new server I'll be o.k.....however is it recommended I also keep the internal domain name the same as the old one or can I change that?

Thanks

Adam
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LVL 35

Expert Comment

by:Cris Hanna
ID: 39253575
You really should run into an issue with changing those, but unless there is a compelling reason...I'd leave them the same.   Remember to run the Setup My Internet Address Wizard prior to creating your users, so that email address are properly created.
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