Yes indeed it should, Nima, but that functionality is not yet implemented. Polyxena actually has an unfinished archive uploader for File Storage that we've been seeking funding to complete and release. See this post:
https://openacs.org/forums/message-view?message_id=113215
(The demo is down, but it's an archive uploader that does what you want.)
In the absence of financing, Ola's implementation, though mainly completed, is on ice. Meanwhile, Lars has added a simple bulk upload feature that doesn't fully solve your needs, as you've noticed. See this bug:
https://openacs.org/bugtracker/openacs/com/dotlrn-fs/bug?bug%5fnumber=930
It would be great if we could get our sleeping beauty into the toolkit. 😊
