This happens to me a lot. Try installing from gem files downloaded
manually. There's some instructions on how to do this here:
http://justaddwatir.com/watir/q-how-do-i-gem-install-watir-behind-a-proxy-server/
Check out the comments section for recent example.
Regards,
Tim Koopmans
I've found that the gem installer works much better if you do a gem
update --system. Unfortunately this can be hard to do also (for the
same reasons).
On one occassion, I did this update on a machine that did not have
connection problems, then I copied the entire ruby directory to my other