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Potential issues on migration from Exchange 2003 to 2010 and Windows server 2003 to 2008 R2

Posted on 2011-04-25
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Good day everyone. We are looking at upgrading Exchange and Windows server OS on a few boxes and would like to know if there are any potential issues we could experience. We will be upgrading our Exchnage 2003 (Windows Server 2003) machine as well as our PDC which also houses Trend Micro network protection, and our customized accounting software.

All our client PCs run Office 2007 and will be upgrading to 2010 after the upgrade to Exchange 2010. All the computer also run a minimum of Windows XP with many on Vista and 7. We also have a BES server on v.4.1.6.9 running on Windows 2003 as a third server and have a Secondary DC which is also our file server running Windows 2003 as well.

If we were to only upgrade Exchnage to 2010 and the Primary DC to Windows 2008 R2, are there any known issues that could experience over all?
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Question by:sscal
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by:Andrew Hancock (VMware vExpert / EE MVE^2)
Andrew Hancock (VMware vExpert / EE MVE^2) earned 400 total points
ID: 35462636
1. Exchange 2003 to Exchange 2010 Upgrade doesn't support in-place upgrade. So your first issues is to obtain a new server, Exchange 2010 is installed as a new server in the same organisation, they will co-exist correctly, and then  you migrate the mailboxes from Exchange 2003 to Exchange 2010.

2. Again for Primary DC (2003) to Windows 2008, I would recommend installing Windows 2008 on a new server, the two will co-exist, and then migrate the roles from DC (2003) to the DC (2008).

So the first issue, you will need to find procure new servers.
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by:sscal
ID: 35462653
I'm sorry that I forgot to mention that but we will be purchasing 2 new 64bit servers and possibly virtualizing both servers.
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by:Kris Montgomery
ID: 35462669
Hi sscal,

There are many potential issues with the migration.  If at all possible, do it in a test environment first.

http://www.google.com/search?sourceid=chrome&ie=UTF-8&q=issues+migration+exchange+2003+to+2010#hl=en&sa=X&ei=ONq1TeXcIZDUgQfApfjGCw&ved=0CBwQBSgA&q=issues+migrating+exchange+2003+to+2010&spell=1&bav=on.2,or.r_gc.r_pw.&fp=76258fd74ceb8990

Most of our issues were with Blackberry devices and other phones that get email.  Many needed resyncing or reset.

Thanks.
mug
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Okay, well if you are doing the virtual environment, then there is no reason, why you cannot do several rehersals.
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by:sscal
ID: 35462731
We do not have the luxury of doing this in a test environment first as we are a very small company and small IT staff. I have used the search engine prior to posting to find potential issues but couldn't find a concrete list of some sort.
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ID: 35462740
Well if you are not prepared to test, you must accept the risk of failure.

There are no real issues, if you prepare correctly.
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by:sscal
ID: 35462742
The virtual environment is a possibility but I don't much about virtualization so I am unsure if I will be doing it with the new servers. Lets leave the virtualization out of this topic. I am simply focused on discussing possible issues with Exchnage, BES, and the Windows server environment.
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by:sscal
ID: 35468850
Are there any other possible issues that anyone can share?
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by:Auric1983
Auric1983 earned 800 total points
ID: 35487901
You will need to upgrade to BES 5.0.3 to support Exchange 2010. There are also some security changes needed on your Exchange 2003 server (due to the BES)

You should also verify your backup and AV software support Exchange 2010.

There are also a number of things to look at when virtualizing Exchange.

I have a really good PDF transition guide, but I'm on my mobile, I'll post it when I get home...

There is also a Exchange 2010 pre deployment analyzer you can download and run in your environment.

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by:aoakeley
ID: 35489600

> I have used the search engine prior to posting to find potential issues but couldn't find a concrete list of some sort.

I know this is not an answer but felt like giving my 2c worth. Ignore it if you think I am being an idiot.

There is no concrete list of potential issues. Especially as what I might consider a minor inconvenience or speed bump someone with less skills might consider a major issue. And what I consider a major issue someone with more skills than me might consider to be nothing. So it's all a matter of perception. Anything can go wrong at any time and for no discernable reason. Either you have the confidence/skills to undertake the task or you dont. If you don't have the confidence, testing in a VM scenario is a good idea. If you think you do not have the time to test, do you have the time to recover it it goes wrong? In my experience the more skilled the engineer the more they want to test, and the slower they go, but the better the outcome is in the end.




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Auric1983 earned 800 total points
ID: 35490827
sscal,

First things first you must upgrade your BES server to 5.0 first in order to support Exchange 2010.  This upgrade is fairly easy, you can do an in place upgrade of your existing 4.1 server, your users will be without BB service for 1 hr or so while you upgrade... Assuming you have a T-support contract the upgrade is free otherwise you have to pay for it.  Once you get it upgraded to 5.0 the config guide is here http://docs.blackberry.com/en/admin/deliverables/16598/BlackBerry_Enterprise_Server_for_Microsoft_Exchange-Installation_and_Configuration_Guide--1091951-0615124404-001-5.0.2-US.pdf 

Here is a link to the rapid transition guide I mentioned in my previous post.  It's a really good overview for migrating a simple environment.

http://msexchangegeek.com/2010/01/30/rapid-transition-guide-from-exchange-2003-to-exchange-2010/

A link to download the pre deployment analyzer - This will ensure your AD forrest & schema are at the correct level, Exchange 2003 is at the correct SP level etc.  http://www.microsoft.com/downloads/en/details.aspx?FamilyID=88b304e7-9912-4cb0-8ead-7479dab1abf2

I spent a day working through my Exchange 2003 - 2010 migration in a virtual environment.  It was actually a simple setup, I setup two VM's on my computer (using Virtualbox)  the first VM was server 2003 R2, running AD, DNS, etc. and Exchange 2003.  The second server was a 2008 R2 server running Exchange 2010 SP1.  I created a few user accounts & mailboxes on the 2003 box sent some fake messages etc.  I then went through the rapid transition guide.



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