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Last night I finished upgrading Windows Server 2003 to the Windows Server 2008. Here are some tips to help those of you facing the same challenge. I had some problems along the way that I could have avoided with more careful planning, but live and learn.

As I use my server only for personal development purposes, it is not that critical as a real production server would be. Anyway, good preparation makes things easier. I chose to do a “clean” installation, as I wanted to install the Windows Server 2008 to a bigger volume.

This is a long post, but if some part helps someone even a bit, it serves its purpose. I’ll cover these tips:

1. Make a checklist for yourself
2. Backup and copy everything to a safe place
3. Prepare post-installation setups
4. Check your hardware compatibility
5. Post installation tasks
6. Installing and configuring applications

Disclaimer: Please remember, that I’m more of a developer/software architect kind of guy than an IT professional who maintains servers full time. I just admin my own servers and desktops when I need, so not all of my tips may be the best practices.

1. Make a checklist for yourself

Before getting your hands dirty, list all the things you have to take into consideration. I used Microsoft Office OneNote 2007 to take my notes. My server is a typical web server with SQL Server so this post mostly revolves around related things.

In the checklist I listed things like:

1. What should be backed up
2. What sites and application pools I have in IIS6
3. How do I migrate databases in SQL Server 2005
4. What other applications I have and what should be reinstalled
5. How should I backup and restore contents in the Windows SharePoint Services
6. Screen captures from various settings pages (IP-settings, IIS, local users, file shares)

I should have checked these things, too:

1. What hardware the server has and is it supported
2. Get the latest drivers for Vista and Windows Server 2003, if there are no native Windows Server 2008 drivers.

2. Backup and copy everything to a safe place

After you have made at least some plan, execute it by copying all the settings, files, databases etc to a place that can be easily accessed after upgrade.

Also, if you have some external USB drive, copy them there. I had lazily put most of the backups and post-installation setups to the backup raid that required drivers to work. If I wouldn’t have been able to get it to work, I could have been in trouble. Separate USB disk would have been safer and compatible whatever happened.

Here are some detailed tips:

SQL Server 2005: I detached the databases and attached them after installation of the new Windows Server. There were only few important databases, so this was faster way than the backup/restore -way. If you want to move your logins, scheduled jobs and other database server wide-stuff, remember to backup at least master and msdb -databases. If you do it manually like me, make sure you know or can locate the passwords for the logins that your apps. may use (connection strings etc).

IIS6: There are some tools that help migrating the database, like the new MS Deploy -tool. I considered using it, but I couldn’t install it since it required .NET Framework 2.0 SP1 that wouldn’t install on my Windows Server 2003 for some reason. So I decided to manually copy everything and configure them in IIS7.

WSS: I only use Windows SharePoint Services v3 to sync my OneNote -notebooks between work and home, which is very handy (I’ll try to blog about it later). After checking the sites and their contents, I decided that again it is easier to copy the files manually and setup the few sites I have manually.

First I considered backing them up with the stsadm, but then I noticed that due to DNS/router configuration, I couldn’t actually access the WSS from the localhost and fixing it would have taken more time than manual way for that small amount of data.

DNS server: I just copied the %systemroot%\system32\dns -folder to safe place.

3. Prepare post-installation setups

Remember to think through the whole process. Backing up the data and installing the Windows Server 2008 is only half of the process and what follows is re-installing the applications you need.

This will be much easier and faster if you reserve all the setups, service packs and product keys to one place.

If you are going to install applications from an .iso-image, you’ll need some program that can access them from the Windows Server 2008. I have been a long time user of the Daemon Tools, but over the last few years I have liked it less and less (ad-ware, reboot during installation, problems in Vista etc). I decided to try the free MagicISO, which works fine for me in Windows Server 2008.

4. Check your hardware compatibility

This may sounds obvious, but actually I neglected to do this, since:

• a) I haven’t had driver issues for a long time with Windows so I took it for granted that everything would just work
• b) Installation on the virtual server went so smoothly – though on a different computer.

My server is built from old computer parts so it has actually some very old parts, now that I think about it. What was supported out of the box in Windows Server 2003 isn’t necessarily supported in the Windows Server 2008.

When troubleshooting my issues, I came across Windows Server catalog of tested products -site, where you can get some idea about supported hardware and software. Remember, many things have changed during the last 5 years and some of my components were old even then

Here is the hardware that caused problems for me:

1. I had no DVD-drive on my server This hit me first as I hadn’t even considered it could be an issue. The server had some old SCSI CD-ROM drive but as the Windows Server 2008 comes on a DVD-image, it didn’t help much. Luckily I found some old IDE-DVD-ROM that worked fine.
2. Windows Server 2008 didn’t recognize my Adaptec AHA-2940UW -SCSI adapter. This hit me when I got to the part in the setup where I was supposed to choose the hard disk – Setup didn’t find any :S Windows Server 2003 drivers didn’t work, but luckily Vista drivers worked. I put them on an external USB hard disk where it found them and I could continue.
3. Finally, I have a backup mirror raid setup on Promise FastTrak TX2000 controller. It wasn’t recognized automatically, either, but after installation I got it to work through the Device Manager with Windows Server 2003 -drivers. Phew.

So, before starting the installation, take note of your hardware (especially legacy ones) and put the drivers to some easily accessible location, like some USB-disk or thumbdrive.

5. Post installation tasks

Except for the driver problems above, rest of the setup went without hitch. What happens next is the initial things to do after logging in.

First you should configure the computer name, domain/workgroup, IP-settings, virtual memory, users etc. This is easily done in the Initial Configuration Tasks -tool that collects everything together. Sweet. Changing of the computer name requires still rebooting, bummer. This was one place where the screen captures of IP-settings etc helped. I haven’t memorized my external DNS-addresses, for example.

Next you need to choose which server roles you want. This is subjective to your needs, but I decided to go with the following developer-oriented roles:

It is also a good idea to take captures of the settings, should you need them later, like in disaster recovery. After that you can choose which features to install.

Activating the Windows Server 2008

I like how you don’t need to enter the product key during the installation, but how it is done after the installation. It makes the installation experience much smoother and faster, as the awkward typing of the long key doesn’t cut the flow.

After the installation I tried to activate the Windows Server 2008, without first entering the product key. I was greeted with obscure “Activation Error – DNS Name does not exist” -error. If you get the same error, enter the product key first and then try activation again.

6. Installing and configuring applications

Finally, after you are satisfied with the configuration of the Windows Server 2008, it’s time to install the applications and updates.

After installing the MagicISO, I installed SQL Server 2005. Windows warns about the compatibility, but mentions that you’ll be fine if you install SQL Server 2005 SP2 afterwards.

To take advantage of all the sweetness that the .NET Framework 3.5 offers, I also installed that. You can download the full setup package from here. If you prefer the web install for some reason, it can be located from here.

IIS7 is one of the features I have waited most and after setting up the database server and accounts, it was time to configure the web server. As the GUI has changed a lot, it may take some time to get used to it, but eventually you’ll find the settings you need. IIS.net is a good place for hints.

I just made sure that I got all the most critical applications to work, but I have still some tasks left to do. Anyway, the hardest part is now behind and the fun is about to start as I can now concentrate on the new features offered by this great platform. I’m especially fascinated about the IIS7 extensibility and what it could be used for tuning the web apps, but that’s an another story.

I’d like to hear about your Windows Server 2008 experiences. Did you have any problems or do you have some tips to share?