Connecting to Windows 2000 Server

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?

Yeah. Don't run a Windows server to store Mac files.

Windows (even Server 2003) only supports an obsolete version of AFP, which doesn't support long filenames. And SMB doesn't expose the resource forks of Mac files.

There is a third-party AFP server (ExtremeZ-IP | Products | Group Logic) you can buy to add modern AFP support to your Windows server. The SFM (AFP) and SMB Comparisons on that site address your issues.

Or you could almost buy an actual Apple server for what they're charging, which might not be a bad idea if you're still running Win2K.