Rendering Web Hosting Futile in Windows Server 2008


About 4-5 days ago, me and Cornel thought it would be a good idea to try out Windows Server 2008 beta 3 and while at it, install Visual Studio 2008 Team Foundation Server (TFS 2008) beta 2. This is supposed to be 99% feature complete and the last version before RTM. Sounds promising. The next 2 days were spent obtaining the install kits for Windows Server 2008 beta 3, TFS 2008 and Visual Studio Team Suite 2008 beta 2. Before proceeding any further, I have to mention that I am not a sysadmin, but Ihave previously managed to install TFS 2005 with no difficulties.

Step 1: Installing Win Server 2008

After obtaining the installation kits and the product key (for Windows Server 2008) from the Microsoft website, the installation process was straightforward: burn image to DVD, backup one partition of the hard drive, format said partition, reboot from installation DVD, enter product key, choose destination and finally, wait for about 30 minutes until Windows installs. I have to acknowledge Microsoft’s new achievements in making the installation time shorter.

Step 2: Configuration of Win Server 2008

The initial configuration of the server is very easy, thanks to the dedicated panel that can be found as soon as the OS logs in for the first time. Things that had to be done: create a password for the Administrator user account, configure the computer’s network identity, configure networking settings, configure Remote Desktop (no monitor for the server), configure Automatic Updates. After these easy steps, the video card drivers were installed from the NVIDIA website. Windows Server 2008 uses the same driver model as Windows Vista, so there were no driver issues.

Step 3: Installing IIS 7

The installation of IIS 7 was as simple as adding the “Web Server” role from the Server Management panel that can be found by default in the quick-launch bar. When choosing the features to install, i chose everything that was available. After the installation, I successfully tested the default website (http://localhost).

Step 4: Preparing for TFS 2008

The plan was to install TFS 2005 first, restore our backups of TFS 2005, then upgrade to TFS 2008. The upgrade is officially supported by the TFS 2008 installation kit. First step to be attempted: install MS SQL Server 2005 Developer Edition. No problems here, installation went like clockwork. Next, Windows SharePoint Services 2.0 (WSS 2.0) must be installed in order for TFS 2005 to integrate with it. Note: Windows Server 2008 comes with WSS 3.0 available as an optional feature, but TFS 2005 does not work with it. After wasting half an hour in trying to install WSS 2.0, I found posts on the web from Microsoft professionals saying that WSS 2.0 cannot be installed on Windows Server 2008.

Step 5: Installing WSS 3.0

New plan: Install TFS 2008 directly and then import the work items with a SSIS (SQL Server Integration Services) package. TFS 2008 can work with both WSS 2.0 and 3.0, so i went on and added the Windows SharePoint Server role, using the default installation options (worked just fine when installing WSS 2.0 on Win Server 2003). After installing it, i ran the setup for TFS 2008. After minor setbacks (SQL Server Agent and Browser services were stopped), the SharePoint Validation failed! After a quick look in the TFS Installation Guide, I found out that the default installation (using the Internal Database of Win Server) was wrong (supplementary hint: the websites were configured on a different port than 80). I uninstalled WSS 3.0 and reinstalled using the Server Farm option. I had to configure the new Server Farm manually, but that was easy (choose the Default Website from IIS, choose a SQL Database Server and service user accounts). I also had to add the default website of WSS manually. I spent about one hour trying to do so and failed because of insufficient permissions (i made the user a member of the Administrators role, but in vain). I chose to uninstall WSS again and reinstall it based on local service accounts (Local Service/Network Service).

BIG HUGE mistake. When asked whether i want to remove WSS 3.0 data from IIS I chose yes and accidentally deleted the Default Website from IIS. Consequence: HTTP websites stopped working (duh!). IIS reinstall needed.

Terminal Step: Installing WSS 3.0 (take 2 3) + IIS 7 as extra

I chose to install both roles (Web Server and SharePoint) in one go. Given the fact that SharePoint only installed and did not do any IIS configuration, all went well and after the installer finished, I started the configuration wizard for WSS 3.0. When choosing an existing Website from IIS to configure Sharepoint to, I was stupefied to discover that the Default Website was still missing from IIS! Now, at this point, some of you might say that Windows Server 2008 is still in beta, but i think it’s safe to bet that this was no beta bug. I make this assumption based on the same behavior from WSS 3.0 that appears on reinstalls. If you install WSS 3.0 incorrectly using the internal database of Win Server, after reinstalling WSS, the same settings as before the uninstall are present. It is similar to uninstalling Reporting Services: the databases of the Report Server remain on the data tier.

So now I found myself with no Default Website in IIS. However, I wasn’t the least worried about a little glitch such as this one. I simply tried to create a website named Default Website that runs on port 80. No problems there. After this I realized that now i had to reinstall SQL Server Reporting Services because the site for the Report Server stopped working. After reinstalling, the Report Server’s site would still not work! The site reported insufficient permissions from IIS. After digging for the error on Google, Ifound what permissions I needed to change and where to change them (IIS 7 has a new management console that “hides” settings). Still the report server site would not work, this time with another error message.

At this point I drew the line: I had been trying to install WSS for about 5 or 6 hours and I had enough of software that would not uninstall completely. The answer was clear: format and reinstall the OS.

The title of this post might be exaggerated, but I think that at that point it would have taken me hours, if not days to get IIS 7 back to its original configuration in order to be able to host sites successfully. This brings me back to my appreciation of the small installation time of Windows Server 2008 (1/2 hour).


That night I reinstalled Windows Server 2008. The next day I managed to install WSS 3.0 from the first try. Instead of creating another very long post, I’m just going to dump all my frustration here. The next problem I encountered was the refusal of SQL Reporting Services to recognize the new user I set up. This frustration is not new. I have been struggling for a year to add a new user to SQL Server Reporting Services, on and off. I followed every guideline I could find, given all the permissions I could to that windows user, but other than the user I installed SQL Server from, I could not use another account for Reporting Services (I even tried to have the TFS installer use Administrator account for Reporting Services, but not even that worked, because I needed 2 users that could access the Report Server site and/or the SharePoint default site – one for the TFS services and one for the TFS setup program).

I will make my call to the community now: if anyone has ever succeeded in adding a windows user to SQL Server 2005 Reporting Services, please, please contact me with some instructions on how I can perform this “feat” (I feel just like a little kid at a magic show when I read posts about users who managed to add users: “How do they do that?”).

Getting back to my (slightly miserable) story. After a few hours of frustration, I found out from the Installation Guide of TFS 2008 that I should not configure SQL Server Reporting Services, the installer does that for me. Yeyy! A quick reinstall of Reporting Services without configuration and … another error. The Reporting Services site cannot be accessed by the TFS installer. This was not one of my best moments. Everything collapsed now: WSS 3.0 was properly installed, Reporting Services was properly installed.

What went wrong? This bad, bad feeling of complete and utter failure hit me at that point. It was the morning of the 2’nd day of installations. Cornel can comment on my state at that point, I choose not to. After browsing hopelessly through some documentation and posts online, revelation hit me: the good old principle of incomplete uninstall – Reporting Services uninstall does not delete the old Reporting Server databases. At this point I saw the light at the end of the tunnel: quick removal of the old databases, rerun the installer for TFS 2008, and everything worked!

This is not the end of the story however. It was the middle of the 2nd day of installations at this point. I installed Visual Studio Team Suite 2008 and Team Explorer next. They worked without me breaking a sweat. All that was left was the working item import.

The sure way of doing things would have been to just copy paste the body of the working items into doc files and later copy paste them back into the new TFS. But I was better than that. I tried running the Data import wizard from SQL Server Management Studio to finish the job in 5 minutes instead of 15. I think it is only fair to announce that I ran the import without backing up the pristine databases of TFS 2008. Needless to say, Murphy was watching and so disaster struck: import package failed due to an attempt to insert multiple rows with the same unique key. This was most probably due to key extension in the new version of TFS on several tables. Again, the bitterness hit me. But this time it was all my fault. I had no excuse.

And so, the 3rd day of installations began (with another format, reinstall OS because – you guessed it! – TFS would not uninstall, although this time the installer service itself blew up), and as i am finishing this long, long post, the TFS is up and running (manual import to be performed by Cornel).

Postludium (running out of section names 🙂 )

Always, always, always read the full Installation Guide of any piece of software as complicated as Microsoft Team Foundation Server.

Always, always, always read the documentation on uninstalling software. You never know what it leaves behind.

Never, ever, ever perform dangerous operations without backing up.

If you ever need advice on installing TFS 2008 (single server mode), I’m your man.

If you have added users to SQL Server 2005 Reporting Services, you are just the person I’m looking for.

All this being said, I would like to thank you for reading my rants for so long. I promise to keep my future posts shorter and tackle large topics in several posts, like normal people do.

Thank you for your time,


PS. As a bonus, I am adding 2 screenshots of the Server Manager and one of the general look of Windows Server 2008 below.


5 thoughts on “Rendering Web Hosting Futile in Windows Server 2008

  1. Tudor Vlad says:

    From what I’ve read, you had quite an adventure 🙂 But at least you’ll know how to setup the system when the RTMs come out.

    As for the “Always, always, always read the documentation on uninstalling software”, seriously Cretz, it’s not gonna work.I mean why would I waste my time reading proses on how to do something, when I know how the setup procedure should work (either form previous versions or similar products). Do any of us read the “setup documentation” when we buy a new door, a car,… Maybe the “how to use the new stuff” chapter. But the idea is that the experience should be the same or easier as before.

    PS: let’s hope this happened because of BETA and the RTM will rock 😉

  2. Dave says:

    Reporting Services 2005 is always grief (in my experience).
    The whole user / security model just seems so broken – more like a beta than anything.
    It may work fine for a purely inhouse anything goes approach but as soon as you try and add user based security it tends to go horriblky wrong

  3. Chris Lively says:

    You have obviously never installed TFS before. When I first began the process of installing 2005, shortly after its release, I spent 4 days trying to get it to work. Finally, beaten down, I read the docs. After reading the docs I started over and completed the install in 3 hours.

    With a car, you’re absolutely right the experience should be similar as to what you had before. However, I wouldn’t expect a database server installation to be anywhere near the same thing as installing a notepad replacement.

  4. Cornel says:

    I agree with Chris… It took me 3 days of failed attempts to instal TFS 2005 before reading the documentation. After reading it… the instalation went smoothly. Unfortunatly I cannot say the same thing about upgrading from TFS 2005 to TFS 2008.

  5. Parker says:

    Here is what we did. We called our support guys at Server Intellect where our server is managed and had them resolve the issue. Save time and headaches!

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