Apple is all too aware of the chronic Apple File Protocol authentication issues with 10.5 Server. Some people have fixed this with a cron task that restarts AFP, say, every night. In my experience, this starts to corrupt file sharing altogether, to the point that, eventually, nobody can log in over AFP.
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.