Creating New Content in Offline Folder

Just set up offline file sync for one of my clients on his Windows XP
laptop. The server folder in question is easily sync'd to his laptop,
and he has no problem accessing and/or modifying those files when he's
disconnected from the network.

The problem is the reverse. When he's not on his network, and creates
new files, those files do not get sync'd to the server when he connects.
Even if he does a manual sync, the files are not there. To make matters
worse, once he saves the files - and he does save the files; I've seen
it - he can't find them again, if the "save" location was the offline
folder.

So two questions:
1. Can you create new files in an offline folder, when you're offline,
and if so, how do you set that up ('cause I've obviously done it wrong)?

2. How do I help him get his files back that he created at home last
night, and didn't listen to me when I told him to save them somewhere
else first?

grep