Windows Server 2008 – Migration Advice

Microsoft’s Windows Server 2008 – Migration AdviceWindows Server 2008 - Migration Advice

The purpose of this section is to help you migrate to Windows Server 2008.  In particular, I want to give you independent advice on the improvements from Windows 2003 to Windows Server 2008.

Firstly, a quick terminology check, this section is about Windows Server 2008;  during development it was know as Longhorn.  Talking of names, as of the summer of 2008 the acronym W2K8 does not seem to have captured people’s imagination in the same way that W2K or W2K3 did for earlier servers.

Topics for Windows Server 2008 Migration


In-place Upgrade v Migration

Avoid upgrading an existing Windows Server 2003 to Windows Server 2008, instead, favour migrating to a brand-new server with a freshly installed copy of Server 2008.  ‘Go for a migration, avoid the upgrade’ has been my cry right from NT4, it seems to me that more and more experts are recommending this strategy.  This is what Microsoft themselves say: ‘We recommend that you perform a clean installation of Windows Server 2008 whenever possible.’

To digress, there are times when you benefit from ditching all that old baggage.   Have you noticed how much space you gain if you redecorate a room?  How much rubbish you throw out if you paint the walls and ceilings?  Well it’s the same with a fresh installation, you get rid of all those old files that you don’t really need.

Microsoft Assessment and Planning (MAP) Solution Accelerator

Readiness is Microsoft’s buzzword, or key concept for migrating to Windows Server 2008.  Let us make our mantra ‘Don’t miss a chance to do IT better with Windows Server 2008.’

Microsoft has been developing readiness / migration tools going right back to NT days, here in 2008, is an easy-to-use, but sophisticated tool known as MAP or MAPSA.  If you expand the acronym MAPSA then the resulting phrase says it all: Microsoft Assessment and Planning Solution Accelerator.  Naturally this tool is free as Microsoft want you get your migration right.  Some people lose sight of the fact that while Microsoft want to make money, they realize that they will only profitable if people successfully install their products.

My point is that while Microsoft has their weaknesses, installation instructions is not one of them.  Thus it’s up to you to position your self on the spectrum from Gung-ho Guy who always installs Microsoft products without reading any instructions, to Mr Conscientious who reads every readme note, help file and relevant KB article, before he takes off the cellophane from the Windows Server 2008 DVD cover.

My strategy is get a test machine.  Install the operating system by following my nose.  Then try and get it to ‘do stuff’.  If it does not do what I want then I research that aspect using techniques I mention in this article.

Only when my test machine(s) are working to my complete satisfaction do I install the production servers.

Microsoft’s Own Free ToolsMicrosoft Tools for Windows Server 2008

With Microsoft Assessment and Planning (MAP) Solution Accelerator you get a readiness tool that includes hardware assessment and software inventory for migrating to Windows Server 2008.  The two key questions are:

  1. Is your hardware ready for Windows Server 2008.
  2. Is all your software compatible with Server 2008

In the case of software applications Microsoft provide two more utilities, while they are primarily designed to help the companies that design applications, they will check your programs for compatibility.

Microsoft’s – "Certified for Windows Server 2008" tool (Best)

Microsoft’s – "Works with Windows Server 2008" tool

Guy Recommends:  A Free Trial of the Network Performance Monitor (NPM)Review of Orion NPM v12 v12

SolarWinds’ Network Performance Monitor will help you discover what’s happening on your network.  This utility will also guide you through troubleshooting; the dashboard will indicate whether the root cause is a broken link, faulty equipment or resource overload.

Perhaps the NPM’s best feature is the way it suggests solutions to network problems.  Its second best feature is the ability to monitor the health of individual VMware virtual machines.  If you are interested in troubleshooting, and creating network maps, then I recommend that you give this Network Performance Monitor a try.

Download your free trial of SolarWinds Network Performance Monitor.

More ‘Readiness’ Questions

  • Are you clear on your Windows Server 2008 domain concept? 
  • Are you clear about DNS? 
  • What changes will there be if you go to IPv6?
  • What new up-and-coming technologies should you investigate?  BitLocker Drive Encryption, Biometric logon, or RODC (Read-only domain controller)
  • I suggest that you conclude an initial readiness assessment with a cathartic evaluation of where you missed the boat with W2K3.  For example you, choose 32bit instead of 64bit, ignored DFS, overlooked Group Policy.

New Hardware – Readiness

All readers think that Guy is mad when he talks about asking for new hardware when you migrate to a new operating system.  Nevertheless, I will say my piece.  Half the world thinks I am mad because it’s blindingly obvious that Windows Server 2008 needs new kit, the other half say Guy is mad because he does not know my boss, they tell me ‘Pigs will fly before my boss will agree to a hardware spend’.  To those people I say, study how children get toys from their parents, they keep on asking! 

Explain to your boss the killer reason you need to spend on kit is to embrace Virtualization.  This will save money, for example reduced electricity bills, fewer server licences and fewer servers in the long run.  In another meeting, explain that the present hardware does not meet the ‘Readiness’ standards.  There again, just as children know how to manipulate their parents, you probably know which of your bosses button’s to press in order to loosen their purse strings.


Key question, how can we make ourselves future-proof?  If that’s unrealistic, after all we are not crystal ball gazers, how can we position ourselves for the future technology.  To digress, I was talking with my father recently, he said when his father built a house in 1939, there was no mains electricity, but they knew it was coming, so they had the house wired ready for when the village had its transformer.  They continued to use candles for 3 years, but when the local transformer was turned on my father’s house was ready for mains electricity.  Are there any lessons from old-timers that we can apply to migrating to Windows Server 2008?

Role of Vista

Traditionally people migrate the client operating system before the servers, XP was on the desktop before Windows Server 2003 was in the back-office.  The uptake of Vista has been slow, however you can turn this to your advantage and migrate to Vista and Windows Server 2008 at the same time.  Many of the greatest benefits of Windows Server 2008 are only realized when you upgrade XP to Vista.

Windows Server 2008 Editions

You need to be aware of the main editions of Windows Server 2008.  If you are attempting an in-place upgrade, then you are limited to like-for-like, Standard 2003 –> Standard 2008.  However, if you are migrating to new hardware you can change from Standard 2003 to Enterprise 2008 with Hyper-V.  This is another example of how migration always offers more flexibility than in-place upgrades.


Start again, go back to the beginning.  Because we only migrate so rarely, we come into the topic with pre-conceived ideas.  Such as, ‘I will save money by upgrading existing kit’. Or, ‘Hyper-V is mumbo jumbo we don’t need that stuff’.  In reflective moments we begin to see the error of our ways, thus sometimes we just have to swallow pride and go back to the beginning.  Sometimes the only way to make real progress with your migration plan is start again with a clean sheet of paper.

Guy’s Away-day Tip

In a previous life I was a research scientist; one day I took an ‘away-day’ to a lab in Leicester, England.  They were working on similar techniques to me, only they had overcome the crucial difficulties that I was suffering.  In a nutshell, one day of talking with someone who had mastered the technique was worth 6 months trying by myself, I urge you to try the same ‘away-day’ strategy with a migration.

If you cannot visit a physical site where they are migrating to Windows Server 2008, you could try one of three similar techniques.  Scour the internet for migration blogs, post questions about concerns you are having in a forum, or else hire a consultant.  You could also trawl Microsoft’s sites, such as MSDN or TechNet, for case studies describing people Microsoft’s own techies have assisted to migrate to Windows Server 2008.

Guy Recommends : SolarWinds’ Free VM MonitorSolarwinds VM Console Free Download

The best feature of this new this new version of SolarWinds VM Monitor is that it checks Windows Hyper-V.  Naturally, it still works with virtual machines on VMware ESX Servers.  VM Monitor is a clever desktop tool that not only tests that your server is online, but also displays the CPU and memory utilization for each node.

It’s easy to install and to configure this virtual machine monitor, all you need the host server’s IP address or hostname and the logon info. Give this virtual machine monitor a try – it’s free.

Download your free copy of SolarWinds VM Monitor.

How to Ensure A Migration Fails

To gain a balanced perspective it’s useful to play devil’s advocate and look at the opposite point of view.  In the case of migration, this means analysing failures, then eliminating such aspects from your plan.

Common Migration Mistakes
Most bodged migrations include at least two of the following, underestimating the time to configure the new servers, failure to have a test network, unforeseen difficulties of running the old system alongside the new, shortfall in budget, not realising the complexity of a migration.

Project Manager
The success or failure of your migration to Windows Server 2008 will hinge not on technical skills, but project management.  Thus, either hire a project manager or else develop these planning skills to a high level, otherwise your migration will meander aimlessly for years.

Upgrades that are not allowed  (A migration would work)
Microsoft explicitly tell us that none of these will work: Any in-place upgrade from Windows Server 2000.  Migrations from 32bit to 64bit editions.  Cross-language upgrades would corruption, and are thus not allowed.  However you could accomplish any of these changes by migrating to new machines, and installing a fresh copy of the Windows Server 2008 operating system.

Re-inventing the Wheel
Let me be clear, I have an independent personality (I work for myself), thus I am resistant to mindlessly following the crowd.  However, I want to warn you about one group of people that I cannot help, those who want a completely new and parallel method for something that already exists.  I see a number of cases because of my interest in scripts such as PowerShell (and VBScript).

A recent example was a reader who wanted to create a log file, which records all security events on a server, from scratch.  Why not use the built-in security eventlog?  Other examples include people wanting my help in re-inventing File Replication Service, creating a custom email client that is impervious to spam.

Rather than seeking new divergent technology, techies should investigate existing proven programs, then configure them to solve problems in their networks. 

Summary of Migrating to Windows Server 2008

The more you study migrating to Windows Server 2008, the more reasons you can find to avoid an in-place upgrade, and instead, opt for a fresh installation of your chosen edition and language on new hardware.  Your first step is to obtain a free copy of Microsoft Assessment and Planning (MAP) Solution Accelerator.

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Microsoft Windows Server 2008 Topics:

Server 2008 Home   • Overview   • What’s New?   • Migration Advice   • Editions

Features   •Resource Manager   • Add Aero Themes   • GP Preferences

 • Network Performance Monitor   • Upgrade W2k8 R2   • Windows Server 2012