On Wed, Feb 19, 2025 at 01:28:11AM +1100, Viktor Dukhovni via mailop wrote:
> On Tue, Feb 18, 2025 at 07:59:49AM +0000, Mark Delany via mailop wrote:
>
> > I'm seeing a curious submission failure with the latest macOS Mail.app
> > (Sequoia 15.3.1)
> > and wondering whether others are seeing it also. The submission mechanism
> > is via an
> > stunnel into an SMTP server and stunnel/openssl was also recently upgraded
> > so it may be a
> > server-side issue thus my survey here to help me disambiguate.
> >
> > A trace of the traffic shows that when Mail.app sends an email with an
> > attachment it fails
> > to send the final "." <CRLF> sequence to terminate the DATA and thus the
> > Submission server
> > discards the email when the socket subsequently closes.
>
> Is this regardless of the type of attachment sent? I just tested a
> message with an attached ".txt" file, and it got through submission into
> Postfix just fine.
>
> System Software Overview:
> System Version: macOS 15.3.1 (24D70)
> Kernel Version: Darwin 24.3.0
>
> Feb 19 01:14:04 amnesiac postfix/submission/smtpd[2791163]: connect from
> unknown[...]
> Feb 19 01:14:04 amnesiac postfix/submission/smtpd[2791163]: Anonymous TLS
> connection established from unknown[...]: TLSv1.2 with cipher
> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> Feb 19 01:14:04 amnesiac postfix/submission/smtpd[2791163]: AAC1193558A:
> client=unknown[...], sasl_method=GSSAPI, sasl_username=...
> Feb 19 01:14:04 amnesiac postfix/cleanup[2791167]: AAC1193558A:
> message-id=<...>
> Feb 19 01:14:04 amnesiac postfix/qmgr[1110399]: AAC1193558A: from=<...>,
> size=5183, nrcpt=1 (queue active)
> Feb 19 01:14:04 amnesiac postfix/virtual[2791168]: AAC1193558A: to=<...>,
> orig_to=<...>, relay=virtual, delay=0.14, delays=0.13/0.01/0/0, dsn=2.0.0,
> status=sent (delivered to maildir)
> Feb 19 01:14:04 amnesiac postfix/qmgr[1110399]: AAC1193558A: removed
> Feb 19 01:15:04 amnesiac postfix/submission/smtpd[2791163]: disconnect
> from unknown[...] ehlo=2 starttls=1 auth=1 mail=1 rcpt=1 data=1 quit=1
> commands=8
Tried again with a PDF file, and saw no issues:
Feb 19 01:33:32 amnesiac postfix/submission/smtpd[2791163]: connect from
unknown[...]
Feb 19 01:33:32 amnesiac postfix/submission/smtpd[2791163]: Anonymous TLS
connection established from unknown[...]: TLSv1.2 with cipher
ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
Feb 19 01:33:32 amnesiac postfix/submission/smtpd[2791163]: 7A9A493558A:
client=unknown[...], sasl_method=GSSAPI, sasl_username=...
Feb 19 01:33:32 amnesiac postfix/cleanup[2791539]: 7A9A493558A:
message-id=<...>
Feb 19 01:33:33 amnesiac postfix/qmgr[1110399]: 7A9A493558A: from=<...>,
size=1715086, nrcpt=1 (queue active)
Feb 19 01:33:33 amnesiac postfix/virtual[2791540]: 7A9A493558A: to=<...>,
orig_to=<...>, relay=virtual, delay=0.6, delays=0.59/0.01/0/0.01, dsn=2.0.0,
status=sent (delivered to maildir)
Feb 19 01:33:33 amnesiac postfix/qmgr[1110399]: 7A9A493558A: removed
Feb 19 01:34:33 amnesiac postfix/submission/smtpd[2791163]: disconnect from
unknown[...] ehlo=2 starttls=1 auth=1 mail=1 rcpt=1 data=1 quit=1 commands=8
You could try Apple's "Connection Doctor" and enable logging of the
session to record what Mail.app thought it was sending. (But don't
forget to turn the logging off promptly, I've seen logging left on
filling disks to 100% as every IMAP interaction gets logged).
--
Viktor.
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