Can't Update RubyGems
Answer : There is no need to take such drastic steps as completely rebuilding Ruby, reinstalling Rubygems from scratch or installing a version manager to solve this problem. There is simply a dependency cycle introduced by the release of hoe 2.3.0: rubygems-update 1.3.5 requires (among other things) hoe-seattlerb hoe-seattlerb requires hoe >= 2.3.0 hoe >= 2.3.0 requires rubygems >= 1.3.1 I wrote the blog post linked to by zipizap. To recap: If you've already tried to update, uninstall the latest rubygems-update first: sudo gem uninstall rubygems-update -v 1.3.5 Update to 1.3.0: sudo gem install rubygems-update -v 1.3.0 sudo update_rubygems Then update to latest: sudo gem update --system With the release of Rubygems 1.3.6, it looks like this problem may be gone. From the release notes: Development deps are no longer added to rubygems-update gem so older versions can update sucessfully. Oi - I feel your pain. I'll first ask the obvious; ...