Show server info ================ mailsend -v -info -port 587 -smtp smtp.gmail.com mailsend -v -info -ssl -port 465 -smtp smtp.gmail.com STARTTLS + AUTHENTICATION ========================= mailsend -to user@gmail.com -from user@gmail.com -starttls -port 587 -auth -smtp smtp.gmail.com -sub test +cc +bc -v -user you -pass "your_password" Note: Password can be set by env var SMTP_USER_PASS instead of -pass SSL + AUTHENTICATION ==================== mailsend -to user@gmail.com -from user@gmail.com -ssl -port 465 -auth -smtp smtp.gmail.com -sub test +cc +bc -v -user you -pass "your_password" As -auth is specified, CRAM-MD5, LOGIN, PLAIN will be tried in that order. Use -auth-cram-md5, -auth-plan, -auth-login for specific auth mechanism. Note: Password can be set by env var SMTP_USER_PASS instead of -pass One line messages ================= One line messages are specified with -M. Each message can have its own MIME type, character set and encoding type: mailsend -f user@example.com -smtp 10.100.30.1 -t user@example.com -sub "testing oneline messages" -cs "us-ascii" -enc-type "7bit" -M "This is a test" -cs "iso-8859-1" -enc-type "8bit" -M "Das Vetter ist schön!" -cs "Big5" -enc-type "base64" -M "中文測試" Attachments =========== Only requirement of -attach is the path of the file. All other attributes can be specified before -attach with appropriate flags. Note: The flags must be specified correctly for each attachment, otherwise the one specified in previous attachment will be used. By default MIME type is guessed from filename extension, default encoding type base64 is used: mailsend -f user@example.com -smtp 10.100.30.1 -t user@example.com -sub "this is a test" -attach "file.pdf" -attach "file.jpg" But all espects of attachments can be controlled: mailsend -f user@example.com -smtp 10.100.30.1 -t user@example.com -sub test -mime-type "text/plain" -enc-type "7bit" -charset "us-ascii" -attach "file.txt" -enc-type "8bit" -charset "iso-8859-1" -attach "deutsch.txt" -mime-type "image/gif" -enc-type "base64" -aname "flower.gif" -attach "/usr/file.gif" -mime-type "image/jpeg" -enc-type "base64" -attach "file.jpeg" By default, content disposition of all atachments are attachment, use -disposition "inline" to give hint to the mail reader to display it as mail body. Look at FAQ# 1 for details. Including a body ================ Only one file can be included as a body of the mail. If the file is not us-ascii, the SMTP server has to support it. If you include a binary file, result is undefined. mailsend -f user@gmail -t user@example.com -smtp smtp.gamil.com -port 587 -starttls -auth -user user@gmail.com -pass secret -charset "utf-8" -mime-type "text/plain" -msg-body "file.txt"