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sendfile.rb

#!/usr/bin/env ruby

require 'net/smtp'
require 'optparse'

module SendFile

  class CommandlineOptions
        
    attr_accessor :options
    
    def initialize()
      @options = {:tls => true, :recipient => '[email protected]'}
    end
    
    def self.parse
      parser = self.new
      parser.parse
      parser.options
    end
    
    def parse()
      parser = OptionParser.new("Usage: sendfile.rb [options]") do |opts|
        smtp_server_option(opts)
        no_tls_option(opts)
        password_option(opts)
        from_option(opts)
        filename_option(opts)
      end

      begin
        parser.parse!
        require_mandatory_options [:server, :password, :from, :filename]
        auto_assign_options
      rescue OptionParser::MissingArgument
        puts parser
        exit
      end
    end
    
    def smtp_server_option(opts)
      opts.on("-s", "--smtp-server SERVER", "SMTP Server") do |server|
        @options[:server] = server
      end
    end
    
    def password_option(opts)
      opts.on("-p", "--password PASSWORD", "Password") do |password|
        @options[:password] = password
      end      
    end
    
    def no_tls_option(opts)
      opts.on("--no-tls", "Don't Require TLS") do |tls|
        @options[:tls] = false
      end  
    end

    def from_option(opts)
      opts.on("-a", "--from-address ADDRESS", "From Address") do |from|
        @options[:from] = from
      end      
    end
          
    def filename_option(opts)
      opts.on("-f", "--filename FILENAME", "File to send") do |filename|
        @options[:filename] = filename
      end
    end
     
    def require_mandatory_options(mandatory = [])
      missing = mandatory.select{ |param| @options[param].nil? }
      unless missing.empty?
        puts "Missing options: #{missing.join(', ')}"
        raise OptionParser::MissingArgument 
      end
    end
    
    def auto_assign_options()
      @options[:tls] ? @options[:port] = 587 : @options[:port] = 25
      @options[:domain] = @options[:from].split("@")[1]
    end
  end
  
  class Mailer
    def self.send
      options = SendFile::CommandlineOptions.parse

      message = Message.new(options)

      smtp = Net::SMTP.new(options[:server], options[:port]) 
      smtp.enable_starttls() if options[:tls]
      smtp.start(options[:domain], options[:from], options[:password], :login)
      smtp.send_message(message.to_s, options[:from], options[:recipient])
    end
  end
  
  class Message
    def initialize(options = {})
      @filename = options[:filename]
      @recipient = options[:recipient]
    end
    
    def to_s
      boundary = (0...12).map{ ('a'..'z').to_a[rand(26)] }.join
      message = <<MESSAGE_BODY
To: #{@recipient}
MIME-Version: 1.0
Content-Type: multipart/mixed; boundary=#{boundary}
--#{boundary}
Content-Type: application/octet-stream; name="#{basename}"
Content-Disposition: attachment; filename="#{basename}"
Content-Transfer-Encoding:base64

#{encoded_content}
--#{boundary}--
MESSAGE_BODY
    end
    
    def encoded_content
      [File.read(@filename)].pack("m")
    end
    
    def basename 
      File.basename(@filename)
    end
  end
end

SendFile::Mailer.send