Windows Server and Exchange Upgrade Path Advice

Posted on 2009-05-04
Last Modified: 2012-05-06
I'm looking for some advice on the best upgrade path for the following situation.

We currently have a server running Microsoft Windows 2003 Small Business Server (not R2) with 60 user CALs.  I need to replace the server, but at the same time, I need to transition to the standard versions of Windows Server and Exchange.  I would like to upgrade to Windows Server 2008 and Exchange Server 2007 at the same time.  I understand that we can use the transition pack to convert our current SBS 2003 to Windows Server 2003 standard and Exchange 2003 Standard, but once this is done, how do we go about upgrading to 2008 and Exchange 2007?  (Meaning, what licenses would we have to buy?)  Would it be better to just skip the transition pack altogether and buy all the new software from scratch?

Any advice on the cheapest way (while maintaining compliance) to accomplish this transition/upgrade would be appreciated.
Question by:I_play_with_DNA
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LVL 58

Expert Comment

ID: 24297317

Is there any reason why you 'need' to migrate away to the Standard Editions of Server 2008 and Exchange 2007? There is a supported migration path up to SBS 2008 (which includes Exchange 2007), which will probably prove to be much cheaper for you in the long run.

If you are having to migrate away because you will hit the 75 user limit in the future, you need not worry. SBS 2008 is now only recommended for 75 users, but a powerful-enough server can support many more than that. All you have to do is purchase enough CALs. There is also Essential Business Server (EBS) 2008 which is a solution which spreads across 3 servers and is designed for networks up to 250 - 300 users.


If you are migrating and Standard Server 2008 / Exchange 2007 is your only option, you do not need a transition pack. That is only required if you want to continue using the SBS 2003 as a standard server. If you will demote the SBS, the procedure is:

1) Introduce new Server 2008 Standard. Promote to DC and then GC in domain, and install DNS.
2) Install Exchange 2007 onto second server and move mailboxes.
3) Migrate data off SBS 2003.
4) Just before you remove the SBS 2003, transfer the FSMO roles off it to the new DC and demote it (dcpromo). Then disconnect it from the network and do not reconnect it.

This procedure is a standard migration and does not require the transition pack.

You should really talk to your Microsoft Licensing Partner regarding licensing. If you are buying new hardware, OEM licensing may work for you for the Server 2008 OS. However, I would only ever buy Exchange 2007 through Volume Channels; it is very costly otherwise.

LVL 30

Expert Comment

ID: 24297393
From my experience with migrating SBS you're better off doing it from scratch. I've tried the transition pack 3 times and all 3 times had to go back and recreate the user accounts anyways due to an issue with the user's SIDs that was preventing them from being able to login with their original login ID. Changing the user's login would fix the issue but it still wasn't clean.

I know Dell is shipping servers installed with Windows Server 2003 along with 2008 media but it appears as if the licenses are different. They have completely different part numbers but I'm unsure if the 2008 licenses work in 2003.
LVL 58

Expert Comment

ID: 24299336

The author does not need to use the transition pack - I said this in my first comment above. The beauty of upgrading the SBS to new hardware running Windows Server Standard is the transition pack is not required, because the SBS is being demoted and removed from the network. The Transition Pack is only required when the SBS server is being kept active and online, but you need to remove the EULA restrictions from the domain.

By removing the SBS, the procedure is just a standard migration; the SBS component does not really matter in this instance and being an SBS will NOT affect the migration route.

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Author Comment

ID: 24299579

But doesn't the transition pack allow us to keep our CALs so that we don't have to buy them all over again?

Author Comment

ID: 24310461

Do you have a reference from Microsoft that states that the 75-user limit has been removed?  What I've found on their site is ambiguous at best: "SBS was DESIGNED for up to 75 users".  Everything else on the web says that there is still a 75-user limit in SBS 2008.  That's why I was wanting to move to 2008 Std / Exchange Std 2007.  I've considered Essential Business Server, but I don't really want to buy three new servers; I have little use for ISA, Forefront and the second Exchange license (which I assume is there so you can do a Frontend/Backend setup) as I already have products in place that do the jobs of these three items better.

I'm just trying to find a way to accompish this migration without sacrificing everything we've already purchased (mainly the 60 SBS CALs).

LVL 58

Accepted Solution

tigermatt earned 500 total points
ID: 24318277

If you migrate to SBS 2008, you will need to purchase new SBS 2008 CALs. That is, of course, unless you have some sort of Software Assurance on your CALs to enable you to upgrade them. I am by no means a certified in Microsoft Licensing, so don't quote me as 100% correct on this.

To the best of my knowledge the transition pack would enable you to continue using your current SBS 2003 CALs on the 'transitioned' SBS server. However, this is not the route you want to take. The Transition Pack has to have Transition Pack CALs purchased (which can be expensive), and once you have the server back to a normal server, whether you upgrade to Standard Server 2008 or SBS 2008, you will still need to upgrade the CALs to the appropriate 2008 CALs anyway.


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