Scott:

The root of the problem is 2 things:
(1) Adagio tables generally only have room for an 8-character filename so they have to use the operating system's shortname feature for longer names (where AP$Hancock.ADB" becomes "AP$HAN~1.ADB").
(2) The server's operating system has to have the shortname feature turned on (it's often called "8.3 file naming").

In the 1990's the 8.3 file naming feature was always activated. But that is no longer the case.

You can tell whether it's activated by going to the command prompt and using "DIR /X" in a folder where there are longer filenames. If it doesn't display a 8.3 shortname in the format "XXXXX~1", then those filenames don't have a true 8.3 name. That is likely because the feature isn't activated (that's an IT task) or, less likely, the feature is active now but the files were created earlier and therefore didn't acquire their 8.3 names.