upload.rb

# vim: fileencoding=utf-8
require 'rubygems'
require 'net/ssh'
require 'net/scp'
require 'pit'

host = 'ruby-sapporo.org'
conf = Pit.get(host, :require => {"username" => "username", "password" => "password"})

files = ['cs.rdf', 'file1', 'file2']
dest_dir = "/var/www/torisetsu/feeds"

Net::SSH.start(host, conf['username']) do |ssh|
  # upload files to home directory on remote host
  files.each{|f| ssh.scp.upload!(f, "~/", :preserve => true) }
  puts "files have been copied."
  prompt = "password:"
  cmd = "sudo -p '#{prompt}' mv #{files.join(" ")} #{dest_dir}"
  ssh.open_channel do |ch|
    ch.exec(cmd) do |ch, success|
      raise 'Error' unless success
      ch.on_extended_data do |ch, type, data|
        ch.send_data("#{conf["password"]}\n") if data =~ /#{prompt}/
      end
    end
  end
  ssh.loop
end