I'm using: ruby 1.8.4 (2005-12-24) [i386-freebsd5] I'm getting an error that I don't understand when using Net::Smtp. This code works for most messages I've tried: Net::SMTP.start(@smtp_server, @smtp_port, @helo_domain) do |smtp| @users.each do |user| smtp.send_message(mail.to_s, mail.from.to_s, user.email) end end But fails with this error when some messages are sent (notably from Outlook, if that makes a difference): /usr/local/bin/ruby18 /usr/local/lib/ruby/gems/1.8/gems/Rist-0.0.1/bin/receive.rb /home/mark/lists/io-devel/". Command output: /usr/local/lib/ruby/1.8/net/protocol.rb:244:in `write_message_0': private method `sub' called for 143740984:Fixnum (NoMethodError) from /usr/local/lib/ruby/1.8/net/protocol.rb:300:in `each_crlf_line' from /usr/local/lib/ruby/1.8/net/protocol.rb:310:in `buffer_filling' from /usr/local/lib/ruby/1.8/net/protocol.rb:308:in `buffer_filling' from /usr/local/lib/ruby/1.8/net/protocol.rb:298:in `each_crlf_line' from /usr/local/lib/ruby/1.8/net/protocol.rb:243:in `write_message_0' from /usr/local/lib/ruby/1.8/net/protocol.rb:258:in `write_message' from /usr/local/lib/ruby/1.8/net/protocol.rb:287:in `using_each_crlf_line' from /usr/local/lib/ruby/1.8/net/protocol.rb:257:in `write_message' ... 10 levels... from /usr/local/lib/ruby/1.8/net/smtp.rb:316:in `start' from /usr/local/lib/ruby/gems/1.8/gems/Rist-0.0.1/bin/../lib/rist/list.rb:163 :in `send_to_list' from /usr/local/lib/ruby/gems/1.8/gems/Rist-0.0.1/bin/../lib/rist/list.rb:103 :in `process_mail' from /usr/local/lib/ruby/gems/1.8/gems/Rist-0.0.1/bin/receive.rb:15 I don't know if this is a bug or something I'm doing wrong. Can anyone let me know what's happening? Thanks a lot, Mark