VPNs / hostile network / cloud storage

[Kevin Shalla <kshalla () UCHICAGO EDU>]

I have a question about protecting cloud storage synchronization, particularly as it relates to public wireless 
networks.

While I know that when working on a public wireless network it is recommended that you use a VPN, I wonder how 
recommendation relates to cloud storage synchronization.

If I have OneDrive or Box or Google set up and automatically synchronizing my local folders to the cloud, and I connect 
to a hostile network, is that traffic liable to be attacked if I'm not running a VPN? If so, because you need to have 
an active network connection before you can connect to the VPN, it seems that  in order to avoid that attack you would 
have to first halt those synchronization processes, start the network, start the VPN, then restart those processes - 
quite a bit of overhead every time you close and reopen a laptop (which stops our VPN).  Is this a valid concern, or do 
you think these processes are safe over a hostile network?

Kevin Shalla
Manager of Technology
Campus and Student Life
University of Chicago
6030 S Ellis Ave # 289
Chicago IL 60637-2608