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Sure, but it's not like the entire Internet is up at once. If rubygems.org goes off-line, it shouldn't mean you can't deploy your Rails app.

Actually, your web server being able to make requests out on the open internet is considered a security liability.

If it lives behind a proxy, a web server being able to talk to anything but the proxy server and database is a matter of developer convenience.

Why does my personal (or intranet) webapp needs an internet connection to work?