I'm a bit surprised to hear this inability to deploy and yet you can ping the cRio -- have you tried ftp'ing with the cRio just as another way to poke at the beast? On the computer that DOES transfer (or in the mode in which it transfers - wireless) -- goto a browser and type into the address bar
ftp://10.xx.yy.2
where xxyy is your team number (for our team 1967 it is
ftp://10.19.67.2)
If you can see files/directories, then you've successfully made an ftp connection to the cRio. Then switch to the other non-transfer-able computer (or switch off wireless and go to wired mode) - re-do the same test. Whether you are able to ftp or not might help illuminate the issue here. Brad might be able to help a bit more based on these results.
bob