AFP SMB - Windows 2000 issues

We are having a problem connecting to our old Windows 2000 Server.
If we connect using AFP we do not see long file names.
If we connect using SMB we see long file names but do not get the file extensions to show up.
For example Quark files do not show a Quark icon, and if you double click on them they will not open with quark. Also font files loose there and become unusable.

The server is running Windows 2000, Service Pack 4, Server.

Any suggestions?

What is a recent history of the server - any adjustments new or of the sort?

I have a W2000 SP4 and use AFP to connect. Has your drive been changed somehow? Is there a Mac connect set up and not just the PC version? Has the information just be relocated there from a backup? Under Manage>Sharing can you see one or two "drives" I see one for PC and the same drive as Mac.

The loose fonts suggest that the Mac you use did not use file extensions and you should IMO to fit in to the W2K thinking. Connecting current OS Mac to W2k thinking is tricky and I dread resetting it up. You can trick the files to work by forcing an extension like ".qxp(v6) or qxd (v5)" on the quark files.