Operation not permitted - /usr/bin/update_rubygems
When I execute on osx El Capitan:
sudo gem update --system
I got the error:
Updating rubygems-update
ERROR: While executing gem ... (Errno::EPERM)
Operation not permitted - /usr/bin/update_rubygems
ended up installing ruby via homebrew. Install homebrew first:
http://brew.sh
then execute
brew install ruby
after that it worked flawlessly. It has something to do with the native ruby installation.
If you're having issues installing a specific gem after installing ruby through Homebrew (as advised above), try the following:
sudo gem install -n /usr/local/bin GEM_NAME_HERE
Found this thanks to user endoplasmic on this issue thread: https://github.com/sass/sass/issues/1768