Windows Server 2008 - Don't Believe the Hype

Upgrading to Server 2008 from Server 2003, talk about a huge pain in the butt and causing near total aggravation and enormous amounts of agitation. Upgrading to Server 2008 is what I believe to be the largest waste of my time and productivity in the history of Windows operating systems.

My original intention was to upgrade Server 2003 to Server 2008 to get a feel for what would be required on my production Internet servers. All I can say is I am glad I upgraded an old non-production server before going forward with upgrades on all of the machines.

My first indication of problems that lay ahead was when the upgrade installer stopped and advised me that FrontPage 2002 extensions must be removed from the target operating system to be upgraded. Nearly all Windows servers that serve web pages have these extensions installed. I thought to myself, no problem, I will simply use add remove server components to get rid of the FrontPage 2002 extensions. I wish it had been that easy. I of course uninstalled the extensions from add/remove windows components and then re-ran the Windows 2008 installer, the upgrade was still was blocked even though I had removed the extensions.

I ended up searching on the Internet to see if anyone else had the same issue that blocked upgrading from Server 2003 to 2008. I was not alone with the blocked upgrade issue. Many other users were experiencing the same blocked upgrade issue. After following this workaround, I was able to uninstall enough of the server extensions to be able to upgrade rather installing a fresh copy of sever 2008. Only problem is that the procedure hosed all of the websites on the server, so it effectively removed any advantage of a seamless, problem-free upgrade as now I must go back in after the upgrade and setup 150+ websites on the server. If I had been aware of this, I would have not upgraded to Server 2008.

It would have been much easier if during the upgrade option on 2008 that it forced the un-installation of the extensions during the upgrade rather than cause issues for users before the upgrade. Sometimes I think the Microsoft software engineers, programmers and product managers lack any sort of common sense at all. I am serious about this, the upgrade routine is a huge bassakwards mess. If you are upgrading to Server 2008 and are using IIS and/or FrontPage 2002 extensions, you may want to reconsider upgrading. The hassle and extra work involved is not worth the little you gain from upgrading.

One quick thing, no matter what you do whether it be a fresh 2008 install or upgrade assign an IP address to the machine. Do not use DHCP or you will find yourself with reduced functionality because the Windows activation routine will refuse to activate the machine. I wanted to use a DHCP assigned address while I worked on the server and then assign an IP when I put it on our Internet accessible network. The machine would not activate. I got a message from the Microsoft site that my installation may not be genuine. When it does this you cannot access the control panel, use Internet Explorer and a who slew of other items are disable, making it nearly impossible to get to the network properties and adding an IP a static address. I finally managed indirectly navigate to the network properties to add a static IP. Once I assigned the static address, I was able to activate Server 2008.

My best advice is to install Server 2008 if have need for it, If you do not then give Server 2008 a very *wide* berth.

I will have to say that Server 2008 is secure right from installation, maybe too much. Forget about using Internet Explorer to grab device drivers and updates for your server, it is so locked down you can barely browse anything on the Internet except the Microsoft sites. The updated version of Internet Explorer 2007 that is installed in Server 2008 has enhanced security configuration features that lock down Internet Explorer, almost to the point of rendering Internet Explorer useless. If you turn off the enhanced security you can no longer launch Internet Explorer, period. Disabling the enhanced security only makes matter worse.

I will have to say I do like the new server management console. It is quite nice and easy to use. That is about the only thing I like about Server 2008 so far.

That is all I can say or comment on for the moment. I will write a bit more about it as I use the now useless upgraded machine a bit more.

My opinion of Server 2008

If you don’t need to upgrade or do not have a need for the features in Server 2008 save yourself some frustration and aggravations and leave it alone. Seriously.

Microsoft should be ashamed of releasing such an aggravating server operating system. With every release of Windows, it seems to get more complicated and counter-intuitive with each new version. I am scared to even look at (or think about) Windows 7 when it is released. You will probably need several physicists and Microsoft gurus on staff just to login in.

If you must find out more about Microsoft Server 2008, you can visit the Microsoft Server 2008 web site.

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