This has been coming up often enough that it deserves to be posted somewhere visible. If you are trying to use SwitchTower with the stock version of Ruby that ships with OSX, you will fail. The stock OSX version of Ruby has a bad OpenSSL module, which wreaks all kinds of havoc with SwitchTower.

The solution is to install a non-stock version of Ruby, either via DarwinPorts, or Fink, or even just the good-old manual “configure/make/make install” process.