Upgrading to Server 2008 R2 in 8 Easy Steps

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Windows Server 2008 R2 was released just a couple of days ago on September 14th -- so now it's time for you to start thinking about installing or upgrading your Server 2008. Here are couple things to keep in mind.

First, the new Windows Server 2008 R2 can only be installed (or upgraded) on 64-bit servers.  If you have Server 2008 installed on a 32-bit server, you will first need to upgrade your hardware to 64-bit before upgrading to Server 2008 R2.

Another thing to think about is whether you want to install R2 from scratch or run an upgrade. Both options are available so it is up to you to decide.  When it comes to a clean install, it is quite easy and almost exactly the same as installing Server 2008.

Is the Upgrade Free?

R2Well, it depends.

According to Microsoft, if you purchased Windows Server 2008 together with Software Assurance (SA), your upgrade to Server 2008 R2 is free.  If you did not purchase SA, then unfortunately you will need to purchase R2 before upgrading.

How much will R2 cost without Software Assurance?  Microsoft did not publish the pricing just yet but you can contact your reseller and ask him/her what would be the cost for your upgrade.

To verify that the upgrade is in fact free for people who purchased SA, I contacted Microsoft via live chat.  Here is our quick conversation:

  • Jodi: How may I assist you today?
  • Gosia: Hi Jodi, I just have a quick question about Windows Server 2008 R2. If I already have Windows Server 2008 - will the upgrade be free or is there a price tag for upgrading?
  • Jodi: Do you know if you purchased Software Assurance when you bought Windows Server 2008?
  • Gosia: No... I did not purchase Software Assurance...
  • Jodi: Ok, It is my understanding that you will have to purchase the Windows Server 2008 R2 if you did not purchase Software Assurance with the Windows Server 2008.  You will not have to re-purchase CALs, just the server software.
  • Gosia: I see. But if I had purchased software assurance then it would have been a free upgrade, right?
  • Jodi: Correct.  And, customers that had purchased Software Assurance are eligible for Windows Server 2008 R2 before new customers.
  • Gosia: That will teach me a lesson for next time. Thank you for your time. That's all I needed.
  • Jodi: Sure.

So as you can see, purchasing SA is always a good idea and it saves you money in a long run.

Improvements in Server 2008 R2

Why should you upgrade to Server 2008 R2?  Are you going to benefit from the upgrade?

Lisa and I have mentioned a couple of our favorite new features in R2 like the Global Search bar in Active Directory Administrative Center or the Recycle Bin in Active Directory.

But besides the cool toys you're going to get, here are few reasons for upgrading to R2:

  • Better performance on more powerful hardware (Windows Server 2008 R2 can be only installed on 64-bit server)
  • "Balanced" power policy for processors
  • Enhanced Virtual Desktop Integration (VDI) technology
  • Efficient Server Management
  • Enhancements to Hyper-V
  • File Classification Infrastructure (FCI) Feature for data management
  • DirectAccess for remote users
  • BranchCache for remote offices
  • Improved and Simplified Management for SMBs
  • Internet Information Services 7.5 (IIS 7.5)

To read more about these features check out the Top 10 Reasons to Upgrade to R2 from Microsoft.

Upgrading to Server 2008 R2 in 8 Easy Steps

Once you're ready to upgrade your Server 2008 to R2 follow these simple 8 steps.

1.  Start the installation by clicking Install Now.

2.  Select the option to get the latest updates for installation by clicking on that option.

3. Next, select the appropriate version -- I have Server 2008 Enterprise installed on my system so that's the one I'm choosing. Once you make your selection, click Next.

4.  Accept the License terms and click Next.

5.  Now we are ready to select the Upgrade option -- go ahead and click on the selection.

6.  R2 is now going to run a compatibility checker.  If you get a report that some things need to be improved or corrected, you must do that before continuing with the upgrade.

7. My compatibility checker gave me a couple of warnings but nothing major, so I'm going to continue. Once you're ready, click the Next button.

8. Now we wait for the Upgrade to complete.

As you can see it is a very easy upgrade and as long as your compatibility checker turns out ok, you are good to go with your new Windows Server 2008 R2 in no time!

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Gosia Grabowska

Gosia Grabowska is an experienced Network Support Specialist and an expert in Windows Server support. She graduated from DePaul University, Chicago with a Bachelor degree in Network Technologies with highest honors. Gosia has over 8 years of technical and support experience and has worked as Systems Administrator for a high profile law firm, where she managed the Backup and Disaster Recovery plan. Gosia has been a part of the Train Signal team since 2006 as the Product Manager and has written many articles on a variety of topics, including Exchange Server 2007, Windows Vista, Small Business Server, and more. (MCTS Active Directory, MCTS Vista, Network+, Linux+, Project+, PMP)