When I type
gem install sass
I get the following error message
C:>gem install compass ERROR: Could not find a valid gem 'compass' (>= 0), here is why: Unable to download data from https://rubygems.org/ - SSL_connect retur ned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed ( https://rubygems.org/latest_specs.4.8.gz)
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.