Upgrade from IIS5

[RyanHunt]

I have a Windows 2000 IIS5 server with around 40 apps on it. These apps vary in size and complexity but it represents about 9 years of dedicated application development time so the amount of code deployed is NOT insignificant. We have always been very please with the functionality and stabiltiy of this server but we are finally starting to hit the wall on some new development we are doing (for instance, support for Office 12 drivers).

 

We are also pretty familiar with Windows Server 2003 IIS 6. However, if I'm going to dedicate team time to deploying, testing, and refactoring for IIS6, I am tempted to move to IIS7, go through the upgrade cycle just once, and be able to stay put for a while again.

 

So, I'm looking for advice from app dev'ers. Is there an upgrade path from Windows 2000 IIS5 to Windows 2008 IIS7? Is it worth transitioning to IIS7 or go for the much easier transition to Win2K3/IIS6? Do I need to go from Win2k-->to Win2K3-->to Win2K8 for a successful upgrade?

 

ANY advice is appreciated.

 

Thanks

 

Ryan Hunt

[AWS]

If you are going to make the move go to Windows 2008. You are going to have do a clean install no matter what you do. No upgrade path in server environment like there is in desktop operating systems.

 

More than likely your apps will need retooling no matter which version you choose. The problem going from 2000 to 2008 is it is a major kernel version change. NT5 to NT6. Every time you have that kind of change you'll have problems with apps. There are a few threads in this forum detailing the problems devs have had with their apps.

 

You're best bet would to migrate to Windows 2003 which is a minor kernel version change, NT5 > NT5.1.

 

Best thing I can suggest is to download the eval, install it and test it out before you make the final decision.

 

In my case I went 2000 > 2003 shortly after the R2 release and I am just about done transitioning to 2008. I have 2 servers left.

 

If you don't want to make the big leap then maybe a stop at Windows 2003 would be best. OTOH, you'll eventually have to move to Windows 2008 and since R2 is in beta once you do upgrade to Windows 2008 you'll have many years before you have to make this kind of decision again.

 

As far as IIS goes the changes aren't as severe. What runs on IIS5 will run on IIS6 and IIS7 also. The only problem I've had is making sure compatibility mode is turned on for legacy asp apps. Management console in Windows 2008 is a little confusing when you first open it up. Once you use it you soon realize the power of it.