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Installing on a machine missing Ruby headers #1561
That'd be a RubyGems issue, not a Jekyll issue, really. If there are pre-compiled versions of the gems that require native extensions, then it'd be their prerogative to release those. I can't keep up with our gem dependencies and all the different platforms anymore :(
If a VM is possible on your colleague's machine, try an Ubuntu installation and install
Another suggestion would be to recognize this possible workflow in the installation instructions to help users out so we don't need to google around to find out how to resolve the issue. People using Jekyll may not necessarily (or at all) be Ruby developers with a configured Ruby development machine.
There are other users out there on stackexchange running into the same problem, if there's a good way to resolve this (tried weird combinations of installing Xcode and other tools to get the headers installed and eventually gave up), a little documentation could go a long way.