RubyMotion: MailCore

app_delegate.rb

class AppDelegate
  def application(application, didFinishLaunchingWithOptions:launchOptions)

    msg = CTCoreMessage.alloc.init
    msg.setTo(NSSet.setWithObject(CTCoreAddress.addressWithName("Someone", email:"[email protected]")))
    msg.setFrom(NSSet.setWithObject(CTCoreAddress.addressWithName("Watson", email:"[email protected]")))
    msg.setBody("This is a test message!")
    msg.setSubject("This is a subject")

    error = Pointer.new(:id)
    ret = CTSMTPConnection.sendMessage(msg,
                                       server:"smtp.gmail.com",
                                       username:"[email protected]",
                                       password:"xxxxxxxx",
                                       port:587,
                                       useTLS:true,
                                       useAuth:true,
                                       error:error)
    true
  end
end

Rakefile

# -*- coding: utf-8 -*-
$:.unshift("/Library/RubyMotion/lib")
require 'motion/project'

Motion::Project::App.setup do |app|
  # Use `rake config' to see complete project settings.
  app.name = 'HelloMailCore'

  # Configure MailCore
  app.vendor_project('vendor/MailCore',
    :xcode, :scheme => "MailCore iOS", :headers_dir => '.')
  app.frameworks << "CFNetwork"
  app.libs << "/usr/lib/libssl.dylib"
  app.libs << "/usr/lib/libiconv.dylib"
  app.libs << "/usr/lib/libsasl2.dylib"
  app.libs << "/usr/lib/libcrypto.dylib"
end

@aceofspades That's because it's linking to static libraries on the Mac, and not the platform specific ones created by the Xcode build.

Took me a while to figure out the correct configuration, but eventually got it working:
https://gist.github.com/4425691