I'm starting to wonder if it's due to the format of some of the files you're sharing. Go to LW's menu Tools>Options>Sharing & make sure all the extension types of the files you're sharing are included. I know in OS9 it doesn't show extensions at the end of files (these are invisible.) But you can probably guess.

eg: text files will have an extension of .txt or for Word will be .doc And for movies it will depend on movie type: mpeg=mpg, QT=mov, etc. Pics=jpg or photoshop=PSD, mp3's should have .mp3 at the end.

So you might need to add the extensions to the files OR add the relevant extension types to the extensions list mentioned above.

Hope this helps.