Chris Green wrote: > I am trying to debug it by connecting directly to port 25 on localhost > using telnet and composing mail that way.
I highly recommend "swaks" the Swiss Army Knife SMTP, the all-purpose SMTP transaction tester utility program for generating test emails using SMTP transactions. For example: swaks --to u...@example.com --server test-server.example.net Here is an example run here to show how it operates. To demonstrate how easy it makes manual "telnet port 25 debugging". rwp@havoc:~$ swaks --to b...@proulx.com --from b...@proulx.com --server localhost === Trying localhost:25... === Connected to localhost. <- 220 havoc.proulx.com ESMTP Postfix (Debian/GNU) -> EHLO havoc.proulx.com <- 250-havoc.proulx.com <- 250-PIPELINING <- 250-SIZE 104857600 <- 250-ETRN <- 250-STARTTLS <- 250-ENHANCEDSTATUSCODES <- 250-8BITMIME <- 250-SMTPUTF8 <- 250 CHUNKING -> MAIL FROM:<b...@proulx.com> <- 250 2.1.0 Ok -> RCPT TO:<b...@proulx.com> <- 250 2.1.5 Ok -> DATA <- 354 End data with <CR><LF>.<CR><LF> -> Date: Sun, 16 May 2021 13:48:10 -0600 -> To: b...@proulx.com -> From: b...@proulx.com -> Subject: test Sun, 16 May 2021 13:48:10 -0600 -> Message-Id: <20210516134810.013...@havoc.proulx.com> -> X-Mailer: swaks v20181104.0 jetmore.org/john/code/swaks/ -> -> This is a test mailing -> -> -> . <- 250 2.0.0 Ok: queued as EB48316A -> QUIT <- 221 2.0.0 Bye === Connection closed with remote host. It reported the queue id in the transaction log. Let's look for it. (I am going to redact just one little string pattern to avoid more noise to my logs from abusers scraping and trying. But I don't think it detracts from the otherwise real example use of it.) rwp@havoc:~$ grep EB48316A /var/log/mail.log May 16 13:48:10 havoc postfix/smtpd[13034]: EB48316A: client=localhost[127.0.0.1] May 16 13:48:10 havoc postfix/cleanup[13037]: EB48316A: message-id=<20210516134810.013...@havoc.proulx.com> May 16 13:48:11 havoc postfix/qmgr[28771]: EB48316A: from=<b...@proulx.com>, size=478, nrcpt=1 (queue active) May 16 13:48:11 havoc postfix/local[26122]: EB48316A: to=<[[redacted]].proulx.com>, orig_to=<b...@proulx.com>, relay=local, delay=0.26, delays=0.16/0/0/0.1, dsn=2.0.0, status=sent (delivered to command: IFS=' ';exec /usr/bin/procmail || exit 75 #rwp) May 16 13:48:11 havoc postfix/qmgr[28771]: EB48316A: removed In the above, and in your logs, the "status=sent" follows the tracing trail of where the message went. It did not disappear. It was delivered. And in your log your messages were the same. Those messages were relayed as described by Bill in his response. I just wanted to say that swaks is much easier and less error prone for injecting test message probes than typing the protocol transaction in manually from the keyboard. Bob