Send email from Outlook Express to gmail then back to Outlook Express

[briarrabbitt]

Hi Everyone, I've been turning this over in my head now for some time
and wanted to see what everyone else thought about this.
My boss has two offices about 400 miles apart from each other and he
has a gmail account. I've set it up through Outlook Express to
download his gmail to each computer. Now my employer is an older
fellow who is really not that tech savy (that's why he's got me) and
he always forget his flash drive so he's taken to using gmail as his
temporary storage between the two offices. What he does is emails any
work he might need to himself from Outlook Express to his gmail
account and then drives the 400 miles and gets on his other computer
and downloads it there through Outlook Express, does his work and then
sends it back to his gmail account and drives the 400 miles back.
But when he gets back and fires up Outlook he doesn't receive the
emails he forwarded. We can get on a web browser and log into gmail
and see the emails and do everything normally but they won't download
to this one computer through Outlook Express. I had thought it had
something to do with gmail seeing these messages and thinking they'd
come from him so they weren't going to resend them back to him but I'm
really not sure. I've gone through the setup of Outlook for gmail
about a thousand times and don't see anything I did wrong, but I can't
see what is different from the computer that is 400 miles away versus
the one I have in front of me. Anybody got any suggestions? I was
thinking I could make some kind of rule in gmail, but haven't had any
luck yet.