I tried to update gem behind a proxy and got the following error message:
sudo gem update --system ERROR: While executing gem ... (Gem::RemoteFetcher::FetchError) Errno::ETIMEDOUT: Connection timed out - connect(2) for "api.rubygems.org" port 443 (https://api.rubygems.org/specs.4.8.gz)
Though the http_proxy and https_proxy (also in upper case) was set it didn’t work. Trying to set the proxy directly in the command did the trick:
sudo gem update --http-proxy=<the proxy> --system