So I've been switching people to using SMB (Windows file sharing), which sucks just on principle, but it also cuts out Time Machine backups. I am also nervous about it losing Apple-specific file resources.
Anyhoo, at one site where I've asked everyone to connect over SMB, several on the server appeared with weird random file names, such as "_GNEWM~A" or "4UI5WM~7". Didn't matter which machine or which user account I was using to connect.
After some poking around, I figured out that folders and files with odd characters in their path, and especially with spaces at the ends of their names, were the culprits. Extra long names, too.
I don't know if this is an historic problem with OS X Server, and I just never ran into it because most of my clients use Macs, or whether this is specific to 10.5. Regardless, right now OS X Server is hurting my schedule really bad, and I can't believe I'm having to be wary of proferring it as a recommendation.