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I'm using RVM, Ruby 1.9.2, and Rails 3.0.7 A standard kill of the process from another terminal doesn't work, either, but kill -9 does, of course. I found a similar question, CTRL+C to Webbrick server ignored , but it's unclear whether that question is describing the same underlying issue. Also, the resolution doesn't seem to apply, since I'm not using :git in my Gemfile. update 1: (old now... see update 2, below, for the real scoop) I managed to narrow the issue down to a single gem. If you source the following test script, you can see the issue, too (assuming you're on Ubuntu 11.04... there was no issue in 10.04) rm -rf tmpkilltest rvm 1.9.2 rvm --force gemset delete tmpkilltest rvm gemset create tmpkilltest rvm 1.9.2@tmpkilltest gem install rails -v=3.0.7 --no-rdoc --no-ri gem install sqlite3 -v=1.3.3 --no-rdoc --no-ri rails new tmpkilltest cd tmpkilltest echo "gem 'barista', '1.0'" >> Gemfile bundle rails s The fact that the issue is caused by Rails' interaction with a gem leads me to now believe that this question actually is related to CTRL+C to Webbrick server ignored , though the test case above shows that this one is clearly not caused by using :git for a gem. update 2: In update 1 I mentioned that I narrowed it down to a gem. When I went through that gem, I eventually found the real culprit. The gem was making a single system call. I've made a very minor modification to the test script where I no longer load the barista gem, but rather I simply append a single system call at the end of the application.rb. With that system call, ctrl-c doesn't work. Remove the system call and it does work. rm -rf tmpkilltest rvm 1.9.2 rvm --force gemset delete tmpkilltest rvm

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