To reproduce in base ruby and AWS connections on Windows, run
require open-uri open https://s3.amazonaws.com
You will see a similar stack trace to http://stackoverflow.com/questions/9199660/why-is-ruby-unable-to-verify-an-ssl-certificate.
SSL_CERT_FILE, and the value should be the path -
open https://api.stripe.com/v1 just fine, but for some reason I started getting these same
SSL verify thangs from Stripe when using their gem. Turns out they bundle …
What worked for me was dropping into Cygwin and overwriting the Stripe bundle with the ca-certificates package bundle:
cp /etc/ssl/certs/ca-bundle.crt /cygdrive/c/Ruby21-x64/lib/ruby/gems/2.1.0/gems/stripe-1.35.1/lib/data/ca-certificates.crt