IIS 5, migrating from .net 1.1 to .net 2.0?
This is not technically supported. The reason it is not supported is because IIS 5 runs on Windows Server 2000 and Microsoft no longer supports Windows Server 2000 ... at all. New security fixes have not been released for Windows 2000 and have not been for several years. In other words, any security issues discovered since July 2010 are still open and accessible to this system, no matter how much work you've done to keep it going. You really need to convince the customer to replace the car. Anyone still running Server 2000 almost deserves a hack.
That's aside, based on the system requirements listed on the .NET 2.0 download page , it looks like you can install .Net 2.0 sp1 on a Server 2000 SP4 machine. It should work in the basic sense, because it was only supported once, even if it wasn't already.
ASP.Net made several significant changes in the transition from .Net 1.1 to .Net 2.0. It's hard to say how much work the update will be, but it probably won't be easy. My advice would be to convince the client to get a new server to host the migrated project with a new and supported version of Windows Server (at least 2008 R2 if you want it to be supported for a significant period of time). This aligns with the need to ditch Windows Server 2000. Copy the project as a new server and do what you need to do to get it working and test it under a recent version of the .NET Framework ... and for what it's worth, it probably won't be much more work to go straight to .Net 4.0 than 2.0 and bring the project to current practice.
This allows you to do whatever you need to develop without affecting the production system, no matter how easy or difficult the upgrade is for you. When everything is ready, your development server will become the new production server. Redefine the end users to the new server, perhaps by changing the dns entry or renaming the new machine with the old name and IP address and possibly moving some database information.
In short, while you want to be asked to do this, it is seriously impractical.
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Easy answer at first: Yes. IIS 5 will support .NET 2.
Hard answer two: The level of effort to update a .NET 1.1 site on a .NET 2.0 site really depends on your site: links to libraries, templates used, etc., so no one here can give you a good answer to this question. I can say that the upgrade to the .NET Framework from 1.1 to 2.0 was pretty big. There is a lot that is new in 2.0 and I believe there has been a decent amount that has been discontinued as well. There is a chance that a lot of things could break on your site, but there is a chance that there will be very few things (or even nothing!) On your site. The only way to know is to do this.
If I were you, I would set up a test environment with .NET 2 and IIS 5 and just unload the site as before. Click on the site and see what works and what breaks.
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