It would be even better if hobo could detect this on installation and suggest the appropriate fix.
We can add a check earlier at run time, but I don't think it's possible to add it at install time. I asked the question on stack overflow: http://stackoverflow.com/questions/5830835/how-to-add-openssl-dependency-to-gemspec
Suggesting an appropriate fix is also hard to do because the fix is different for each operating system, and depends on whether you're using rvm or not. We might be better off not suggesting anything, because, quite frankly, googling for LoadError, openssl and your operating system might be the best solution.
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