gem install cannot download from rubygems.org

Question

When I type

gem install sass

I get the following error message

C:>gem install compass ERROR: Could not

Answer 1

I have experienced the same symptoms on Win7, Ruby 2.1.5 64bit - different gem, but same error message.

In my case, I had to install a new root certificate for rubygems, this link describes how:

https://gist.github.com/luislavena/f064211759ee0f806c88

The reason is that the ruby installation contains its own set of root certificates which are used when establishing secure connection with rubygems.org - but the certificate has since been changed on the server - so none of the root certificates that comes with this ruby installer can validate the server certificate. That is why you need to update the root certificate.