Sinatra email Net::OpenTimeout - execution expired

There are a few other posts about this but after trying those solutions nothing happened. I've tried two different mailers and they both react the same. This is my mailer file:

 Pony.mail({
   :to => 'Iexist_tester@yahoo.com',
   :via => :smtp,
   :via_options => {
     :address        => 'smtp.gmail.com',
     :port           => '587', #also 465
     :ssl => true,
     :user_name      => 'MY-USEMERNAME@gmail.com',
     :password       => 'MY-PW',
     :authentication => :plain, # :plain, :login, :cram_md5, no auth by default
     :domain         => "localhost.localdomain" # the HELO domain provided by the client to the server
   }

 })
 puts('after')

It never makes it to the puts at the end. I know these credentials work as I've set this up this address in a flask app and it works. Not sure what goes in the domain but nothing seems to make a difference. Even entering incorrect data, like a fake PW does not change the error. Logs throughout the function do fire though it is running. The full stack trace:

/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/resolv-replace.rb in initialize
    original_resolv_initialize(IPSocket.getaddress(host), serv, *rest)
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/resolv-replace.rb in initialize
    original_resolv_initialize(IPSocket.getaddress(host), serv, *rest)
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/net/smtp.rb in open
      TCPSocket.open address, port
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/net/smtp.rb in tcp_socket
      TCPSocket.open address, port
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/net/smtp.rb in block in do_start
        tcp_socket(@address, @port)
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/timeout.rb in timeout
        bl.call(klass)
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/net/smtp.rb in do_start
      s = Timeout.timeout(@open_timeout, Net::OpenTimeout) do
/Users/user/.rbenv/versions/2.3.1/lib/ruby/2.3.0/net/smtp.rb in start
          do_start helo, user, secret, authtype
server.rb in block in <main>

Perhaps it is the second to last line? If so, what doe it mean?