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I am having issues with bundle install and bundle update in a Rails 5.0.1 project. I'm working on OS X with OpenSSL 0.9.8.

Error message:

Gem::RemoteFetcher::FetchError: Errno::ECONNRESET: Connection reset by 
peer - SSL_connect (https://rubygems.org/gems/colorize-0.8.1.gem)
An error occurred while installing colorize (0.8.1), and Bundler
cannot continue. Make sure that `gem install colorize -v '0.8.1'` 
succeeds before bundling.

Yes, I have ran the gem installs for EACH gem that gives error. Eventually, the project stops giving error messages, but once I decide to add a NEW gem, the errors start again.

To give a rundown of what I have done to my machine thus far, I updated to openssl 1.1.0c in order to comply with braintree python requirements. This was done for a previous project, however, I think it has something to do with the error messages I am receiving on ROR now.

I have looked on SO for what reset by peer means. Also, after following a rabbit hole, I came across a comment from someone saying that they had the same issue and it had to do with RVM. I didn't bookmark where I found the comment though.

This makes me wonder if having rvm and rbenv and homebrew can possibly be causing the issue? I am aware that I can not get an exact answer due to each machine environment being different. However, if someone can point me to references to setting up/repairing openssl, tls, or whatever else may help me out, I might be able to figure it out.

I am also thinking of just creating a new user on my system, but will everything I have done to the system be carried over to new user?

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limaBEAN
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  • code for project? It's a new rails app. Nothing has been added. – limaBEAN Feb 09 '17 at 18:35
  • Whenever I create a new rails app or when I enter bundle install or bundle update. Since it has to do with ruby gems, I figured to try and use rails 4.2 and ruby 2.3.3 to see if maybe it's just the gems that need to be updated, but no dice. Now I am thinking it has to do with the certificates in the keychain, so I am reading up on that. I just hope I didn't mess things up to bad when switching openssl versions. Need to study up on OSX system. Brain is about to implode. – limaBEAN Feb 09 '17 at 20:37
  • OpenSSL 1.1.0 and OpenSSL 1.0.2 are ***not*** [binary compatible](https://www.openssl.org/policies/releasestrat.html). You should probably check to see what version Ruby expects. – jww Feb 09 '17 at 20:45
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    Now I see why everyone loves SO. Ruby 2.3.3 expects OpenSSL 1.0.2j. The current user I created has OpenSSL 0.9.8zh installed. What do you recommend I use/do to switch? I've read somewhere to be careful linking newer versions of openssl since the OSX comes preinstalled with it. Not sure how accurate that is. I've made a mess of things already. Thinking about nuking hard drive to start on clean slate. – limaBEAN Feb 09 '17 at 20:57
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    OpenSSL 0.9.8 is not binary compatible with anything modern. Your next questions will probably lead you to ... [Brew refusing to link openssl](http://stackoverflow.com/q/38670295), [Update OpenSSL on OS X with Homebrew](http://stackoverflow.com/q/15185661), [How to install latest version of openssl Mac OS X El Capitan](http://stackoverflow.com/q/35129977), [How to upgrade OpenSSL in OS X?](http://apple.stackexchange.com/q/126830), [Openssl installation using HomeBrew fails](http://superuser.com/q/486389), etc. – jww Feb 09 '17 at 21:04
  • Awesome thank you. Thanks for the edit too, however, I did START OFF with using openssl 1.1.0c, Ruby 2.4.0 and Rails 5.0.1. It was only out of frustration that I decided to try project again with openssl 0.9.8, Ruby 2.3.3, and Rails 4.2.0. Either way, it was a no-go. Thanks again. Rabbit hole, here I come. – limaBEAN Feb 09 '17 at 21:08

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