A few months ago, I reported that sometimes, when sending a new DLL on the server, that IIS does not always restart the application properly. Basically, 9 times out of 10, this works. But, sometimes, the new DLL is sent to the server, and IIS will never respond back. In order to rectify the situation, we have to IISRESET /RESTART. And, even with that, sometimes, we have to do it several times.

I thought this was related to the compiled DLL or to the .NET framework, but recently I have upgraded to Visual Studio 2008 and have .NET Framework 3.5 on the server. This didn't change anything. The problem is still there.

This makes me think that the problem could be related to IIS itself. The server is Windows Server 2003 with IIS 6. In order to resolve the issue, do I really have to upgrade to Windows Server 2008?