This is a bit of a challenge because Crystal 9 has been out of support for @15 years. Win Server 2016 probably will not have the correct C++ libraries for running it. So, first off, I would look at Programs and Features for the old server to find which versions of the Microsoft Visual C++ libraries are installed. Crystal 9 is 32-bit, so you will need to install one or more of the older 32-bit versions of those libraries in order for it to work. This must be done prior to installing Crystal.
When you install Crystal, find the setup.exe, right-click on it and select Troubleshoot Compatibility, follow the wizard and set the compatibility to Windows XP. Note that this means that you won't be able to install from a CD - you'll have to copy the files to the a hard drive on the server. After the compatibility is set, right-click on setup.exe and select "Run as Administrator" so that the install can create the necessary registry settings.
Finally, when you configure your application in IIS, you'll need to establish a 32-bit application pool to run it in.
There is no guarantee that this process will work, but it's worth a shot because your only upgrade path would be to rewrite your application as an ASP .NET app.
-Dell
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