Send attachment on Custom made SMTP server

A local SMTP server can be a decent alternative to third-party email services. Find out how to set up your own SMTP server on macOS, Linux, ...

Send attachment on Custom made SMTP server

SMTP has no concept of "attachments" to messages. E-mail attachments are part of the same body of the message that in SMTP is all transmitted between the DATA command and the End-of-DATA indicator (the . "command"). See RFC 5321. Note that there is no way in SMTP to tell the server how much data is going to follow the DATA command, though there is a way for the server to give a limit to the size of a message body (and the reply to the End-of-DATA command might be an error response code and a message indicating that too much data was sent.

You can use MIME to identify different parts of the body of the message, but the creation and interpretation of the message body are entirely outside the scope of the SMTP server. See RFC 2045 and RFC 2046, and the many other related RFCs that refine the MIME specification (including RFC2184, RFC2231, RFC5335, RFC6532, RFC2646, RFC3798, RFC5147, RFC6657).

What tools will you need to mail merge with individual attachments?

  1. All of your attachment files, ready to send
  2. A Google Sheet that lists the email addresses in one column and the file names in the other
  3. A place to host the files, such as Google Drive, Amazon S3, Dropbox, or your own web server
  4. A Gmail or Google Workspace account
  5. GMass installed and connected

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