Mac OS X 10.4 comes with ruby 1.8.2, it seems to have a problem with OpenSSL which causes switchtower to hang when trying to connect to your server.
You can download the source code to Ruby 1.8.3, compile it and install it, but you’ll start getting weird errors in gem when you try to install some libraries.
The solution turned out to be to compile Ruby slightly differently. You need to pass some flags to configure:
./configure --enable-shared --enable-pthread
After configuring it, makeing it, and running sudo make install, I had what seemed to be a working Ruby installation. It installs to /usr/local/bin which is already in my path. Executing hash -r causes bash to re-scan the path, after which executing ruby -v correctly reports
ruby 1.8.3 (2005-09-21) [powerpc-darwin8.3.0]
After that I installed RubyGems-0.8.11 and the rails and switchtower gems, including all dependencies. The installation worked fine, and so did switchtower when I tested it.
I didn’t even need to remove Apple’s Ruby install.
If you do want to remove Apple’s installation of Ruby, you’ll want to back up and delete the following files and directories:
/usr/bin/erb
/usr/bin/irb
/usr/bin/rdoc
/usr/bin/ri
/usr/bin/ruby
/usr/bin/testrb
/usr/bin/gem
/usr/bin/gem_server
/usr/bin/gemwhich
/usr/bin/rake
/usr/lib/ruby/
/usr/lib/libruby.1.dylib
/usr/lib/libruby.dylib
/usr/share/ri/