gem install sass not working on Windows

Oh goodness. It seems like every time I slink away from my Mac back to developing on my PC I spend more time troubleshooting why I can’t get things to install than I do actually developing. Now, is that on me? Possibly. But, dear reader, I am quite good at figuring out what’s wrong. Especially when the answer is on the first Stack Overflow answer I find.

I tried running a ‘grunt watch’ task only to realize I had not installed SASS yet on my PC. So, simple ‘gem install sass’ returned:

ERROR: Could not find a valid gem 'sass' (>= 0), here is why: 
Unable to download data from - SSL_connect 
returned=1 errno=0 state=SSLv3 
read server certificate B: certificate verify failed 

Cool, now I’m the one that’s insecure. Cheap shot Ruby. Anyway, I found a Stack Overflow post with the answer to my problems.

gem source -a

You will be asked if you are insecure want to add this insecure source. Say yes, and behold the many gems now at your finger tips. Try it once more:

gem install sass


That’s right, that’s a bingo. Enjoy the rest of you sassy existence on your PC.

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John Hartley is a Director of Product Engineering at Beam Dental in Columbus, OH. With 7+ years of leadership experience he has worked in startups, agencies, and began his career as a freelance Front End Developer. Always looking to iterate, this blog is a place for him to share his knowledge as well as hone his craft, challenge assumptions, and build a strong base of leadership and management knowledge. Connect with him on LinkedIn

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