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I would like add some custom headers to selected outgoing mail based on a specific domain and the subject line.
To the remote_smtp transport, add something like
headers_add = ${if and{\ {eq{$domain}{spec.dom}}\ {matches{$h_subject:}{whatever}} }\ {Content-Type: text/html; charset="us-ascii"} fail }
This example shows a Content-Type: header, but you can have anything you like, and multiple headers can be inserted by using \n to separate them.
\n