I tried your inline solution: it worked as expected. I saw the mapping happen between postfix/pickup and postfix/qmgr
I finally could get the canonical mapping to change the Return-Path (and the Return-Path only: the From and Reply-To must be left as they are). The only way I found: list ALL sender email addresses in hash:/etc/postfix/canonical. The regexp:/etc/postfix/canonical just did not want to map reliably a domain name to a certain Return-Path, even though I tested successfully all regular expressions with (for example): postmap -q "info[at]ghi.com" regexp:/etc/postfix/canonical when used to test the file listing the following: /@abc\.com/ address_1[at]whereto.com /@def\.com/ address_1[at]whereto.com /@ghi\.com/ address_2[at]whereto.com /@jkl\.com/ address_1[at]whereto.com Those are pretty vanilla regular expressions matching all email addresses of the listed domains. Why "postmap -q" and the actual sending of a message from these domains behave differently I just don't understand. Thank you very much for your help! I appreciate it even more so because this is supposed to be a long weekend (Happy Easter).
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