Upgrading Server 2008 R2 Standard to Enterprise with Exchange 2010 installed on the OS

Hello,
I have recently Migrated from SBS 2003 with exchange 2003 to Server 2008 R2 Standard Edition with Exchange 2010 installed.  Now that the migration is complete we have decided to implement DAG.  The problem here is that DAG requires Server 2008 R2 Enterprise Edition and I am wondering if there are any big nono's to an in place upgrade of Server 2008 R2 with Exchange 2010 installed or if there are any pitfalls to watch out for during this upgrade.  If an in place upgrade is not recommended I would love to here some other proposed solutions.  
merritthornIT directorAsked:
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George SasConnect With a Mentor IT EngineerCommented:
Well , if you want to use DAG , the most pain free solution is to install the second server on R2 , move all the mailboxes to the new server and wipe the old one and re-install it.

I haven't yet tried to upgrade the 2008DC's from standard to enterprise with exchange running. Maybe someone else has and has an idea but mine is the most simple and pain free :)
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mattibuttCommented:
what is your reason for DAG so soon since you used sbs 2003 you have to have a good justification for your action how big is your organisation.
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merritthornIT directorAuthor Commented:
GeoSs-I thought of that but in order to do that we would need to reconfigure all of the Outlook 2003 clients and probably some smart phones and Iphones.  I don't mind the work but people get impatient with that kind of modification to often.

Mattibutt-Well that is a great question.  Namely it was requested.  We had a back-up solution that worked well for Exchange 2003 that made it redundant if we lost the server we could get it back virtual rather quickly.  This solution though is not available yet for Exchange 2010 so DAG is our prefered route.  Main reason is we can also located a DAG member in a remote office for disaster protection.
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George SasIT EngineerCommented:
You don't need to reconfigure the Outlook 2003 clients.
Exchange will do that for you automatically.
Install new server.
Move all mailboxes.
Let the 2 servers run both for a day while clients update the settings.
Clients connecting to the exchange will be automatically redirected to your new server by the exchange.
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mattibuttCommented:
there is a website sbsmigration.com ran by jeff he is specifically expert in migration for windows based platforms i would suggest you dicuess your requirements with him his in depth knowledge will be very crucial for you
http://www.sbsmigration.com/
its not that expensive however as you are aware migration is a very time consuming task at the sametime you have to with LOB applications etc
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George SasIT EngineerCommented:
mattibutt: he allready migrated.
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merritthornIT directorAuthor Commented:
GeoSs - Outlook 2003 Clients do not have Autodiscover so how would they know to update the settings to the new Exchange Server once the original is shut down?  I know that 2007 and 2010 client will update themselves but 2003 need manual changes....Thought.

Mattibut - I will take a look there.
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merritthornIT directorAuthor Commented:
Sorry yes I did already migrate from SBS to Server 2008 R2... Well SBS is still running but does not function as anything but DC.  I am about ready to decomission it too.
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George SasIT EngineerCommented:
I'm not talking about the autodiscover function.
Even in exchange 2003 , when you move a user from one mailbox to another , you don't need to tell outlook that. The exchange server will tell Outlook that the mailbox is moved to another server and redirect the client.
The new server name will be automatically updated also in the outlook profile.
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merritthornIT directorAuthor Commented:
Hmmm when I performed the upgrade the 2003 clients had to reconfigure the mail continued to route correctly but the client setting in outlook 2003 pointing to oldserver.domainname.com had to be changed to newserver.domainname.com.  Of course I sent out instructions on how to change this so I am not sure that they actually had to change it.  I thought they did though.
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TarekIsmailConnect With a Mentor Commented:
Yes, you can upgrade from Windows Server 2008 Standard to Enterprise.
http://social.technet.microsoft.com/Forums/en-US/winserversetup/thread/a9fb29a1-9cad-4d01-9e65-ce9b2b88232b

to upgrade exchnage from standard to Ent , yes you can from Std to Ent only:
Set-ExchangeServer -Identity ExServername -ProductKey aaaaa-aaaaa-aaaaa-aaaaa-aaaaa

but i prefer to move the DC from the server to new one before configure DAG.
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merritthornIT directorAuthor Commented:
Thanks I will check the article.  We will probably just stick with Exchange Standard so no upgrade needed there.  When you say move the DC from the server to the new one before configuring DAG what are you refering to?  When I migrated from SBS I set-up a new DC 2008 R2 and a separate Exchange box so the DC and Exchange are separated.
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merritthornIT directorAuthor Commented:
I saw this article earlier and this is the line that concerns me...

"I performed this operation and it went okay.

AD Certificate services requires additional backup (see the above link mentioned)

The Microsoft Exchange Server 2007 on the server did not start up because rights in the registry was changed and some settings where missing after reboot.

This is only some info for you that wants to perform the same upgrade"
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George SasIT EngineerCommented:
Exchange 2010 STD for DAG (keep in mind your limited on the number of databases: 5) and Windows 2008 Enterprise edition to support clustering.  If you need more then 5 databases then you'll want to go Enterprise.  

And I just noticed now that you never said your exchange is installed on a DC .. my fault here :)

TarekIsmail: you sure there are no issues when Exchange 2010 is also installed on it ?
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merritthornIT directorAuthor Commented:
Exchange is not installed on a DC.  The Exchange server is only that an Exchange server.  The 5 DB limit should be fine for our needs but I will keep that in mind.
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TarekIsmailCommented:
DAGs are available in both Exchange 2010 Standard Edition and Exchange 2010 Enterprise Edition.

In addition, a DAG can contain a mix of servers running Exchange 2010 Standard Edition and Exchange 2010 Enterprise Edition.

your need only now to upgarde your windows Ent.

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merritthornIT directorAuthor Commented:
OK so it sounds like it should be OK to do an upgrade of the 2008 R2 Standard to Enterprise.  My biggest concern is that once the upgrade is done Exchange DB's will fail to mount.  That is never fun.  I am not a fan of upgrades but I figure if I can upgrade then set up the DAG and the cluster then I should be able to take the upgraded server down rebuild it and put it back without having to reconfigure everyone.
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George SasIT EngineerCommented:
Good luck !
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leo2308Commented:
Did the upgrade from Server 2008 R2 Standard to Server 2008 Enterprise with Exchange 2010 installed work out for you ?? I need to do the exact same thing on a production Exchange server for DAG functionality, and am uncertain a about everything running smoothly...
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merritthornIT directorAuthor Commented:
You know I have not performed that upgrade yet.  Originally I was planning on it but now we are focusing efforts on Virtuallizing and getting the virtual environment clustered.  Sorry I could not be more help.  From everything I found on the process it should be fairly straight forward.
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