I ran into a strange ‘bug’ that was a little bit more annoying to debug.
Apparently OpenSSL 1.x that is getting installed by brew doesn’t seem to be 100% compatible with Ruby, at least when you install it using RVM.

I ran into a reproducible problem when trying to connect to a salesforce sandbox account. This could be distilled down to this snipped:

require 'net/http'
require 'openssl'

h = Net::HTTP.new('test.salesforce.com', 443).tap do |http|
  http.use_ssl = true
  http.verify_mode = OpenSSL::SSL::VERIFY_NONE
h.post('/test' ,'')

Which resulted in this sad exception after 30 seconds or so:

Errno::ECONNRESET: Connection reset by peer - SSL_connect
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:799:in `connect'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:799:in `block in connect'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/timeout.rb:54:in `timeout'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/timeout.rb:99:in `timeout'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:799:in `connect'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:755:in `do_start'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:744:in `start'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:1284:in `request'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:1307:in `send_entity'
from /Users/mseeger/.rvm/rubies/ruby-1.9.3-p125/lib/ruby/1.9.1/net/http.rb:1096:in `post'

It turns out that RVM can also install openssl, and it decides to go for version 0.9.8:

$ rvm pkg install openssl
Fetching openssl-0.9.8t.tar.gz to /Users/mseeger/.rvm/archives
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 3690k  100 3690k    0     0   394k      0  0:00:09  0:00:09 --:--:--  456k
Extracting openssl-0.9.8t.tar.gz to /Users/mseeger/.rvm/src
Configuring openssl in /Users/mseeger/.rvm/src/openssl-0.9.8t.
Compiling openssl in /Users/mseeger/.rvm/src/openssl-0.9.8t.
Installing openssl to /Users/mseeger/.rvm/usr

After that I just reinstalled Ruby and pointed it at the openssl version just to make extra sure:

rvm reinstall 1.9.3-p194 --with-openssl-dir=~/.rvm/usr

After that, the snipped ends up with a 404 as expected.