I found a solution to send ActionMailer messages with attachments. The documentation in the wiki is inaccurate, you can''t just add an attachment to an existing TMail object that has been created by ActionMailer. It will not create the proper mime structure. This is just rough code and needs to be cleaned up, but it works for sending multipart messages with attachments. You can easily add both plain/text and html.text parts, as well as loop through a list of attachments. The stumbling block in ActionMailer is that it creates a plain/text e- mail message. Not a multipart/mixed or alternative message structure to start with. mime = Mailer.create_message() # Generate initial message mail = TMail::Mail.new # Create a new mail object mail.parts << mime # Insert plain or html text part mail.parts << attachment # add attachment # Copy required headers mail.to = @mime.to mail.from = @mime.from mail.subject = @mime.subject # Deliver message Mailer.deliver(mail) To create an attachment I found this worked fairly well. Although you must encode the attachment content or TMail _may_ ignore it. attachment = TMail::Mail.new attachment.body = Base64.encode64(content) attachment.set_content_type(file.content_type, "name" => file_name) attachment[''Content-Transfer-Encoding''] = "base64" attachment[''Content-Disposition''] = "attachment; filename=\"# {file_name}\"" This need a lot of work still. But it works. -- Lon Baker Speedymac LLC http://www.speedymac.com AIM: spdemac Skype: spdemac