I’ve had some trouble installing gems on windows instances using
bundle install. I had this problem first at ~2009. The problem is missing certificates.
While this fix is correct, a quick and dirty approach is to make sure that your gem files have source http instead of https:
# A sample Gemfile source "http://rubygems.org" gem 'albacore' gem 'nuget_helper'
This means that the communication to download gems from rubygems is not private.
Comments or errors? Fork post and do a pull request on github