I had a situation a while back befor I got my sandisk cf reader. I had to rig vterm and the native windows program hyperterminal for serial transfer. The hyperterminal did not have a queuing function so I found IZARC and packed a bunch of files and made the transfer. Couldn't pack them in ZIP beacse I only had lha support in the Amiga. Thats how I found IZARC.
EDIT:
@spihunter
You answered while I wrote. No I don't think Winrar does anything like that. A distant bell rings that Winace did that at some point. I haven't tested winace in a long time. I always used winrar but IZarc is rather nice so I probably keep it.