We have a legacy box (windows 2000) and have hit the wall for its life. We are going to slowly upgrade and are looking to know if Web Connect 3.5 will work on a Windows 2003 server. We ask for version 3.5 since that is the currently used version.

Perfect legacy fit!

Web Connection should also work on the newest version of IIS. The ISAPI module can run on any version and frankly I would not recommend running on server 2003. Security is a huge concern since Microsoft won't patch that old version so it's much more prone to known security issues.

I would try out Server 2016 and see if that will work for you - if nothing else you can create a VM in 2016 and run 2003 in that, but I don't see any reason why 3.5 wouldn't run on 2016. No reason to incur that extra technical debt before you even start putting hte server into production.

+++ Rick ---