On 2/4/2026 8:50 PM, Viktor Dukhovni via Postfix-users wrote:
On Wed, Feb 04, 2026 at 10:18:00AM -0500, Dennis Putnam via Postfix-users wrote:

It may be time for more debugging info. You could always add a -v
parameter to the smtp service in master.cf that will give you more
verbose info (so long as this is a server where you can safely do this
kind of debugging)

smtp      unix  -       -       n       -       -       smtp -v

That will certainly show the smtp session including which user is being
used for authentication and the result.
That's the master.cf entry for the Postfix SMTP CLIENT (smtp(8)), not
the Postfix SMTP server (smtpd(8)).  See side-by-side definitions below:

     $ postconf -c ~/dev/postfix/postfix/conf -Mf 'smtp/*'
     smtp       inet  n       -       n       -       -       smtpd
     smtp       unix  -       -       n       -       -       smtp

After resolving a higher priority problem, I am back to this one. I've added
the -v option but I'm not sure exactly what to look for. I do see something
suspicious.
You've added the "-v" to the wrong service:

2026-02-03T14:48:59.408005-05:00 dap002 postfix/smtpd[142495]: >>> CHECKING
Recipient address VALIDATION MAPS <<<
Don't confuse the SMTP delivery agent (SMTP client) "smtp/unix" (daemon
program smtp(8)), with the port 25 SMTP listener (SMTP server)
"smtp/inet" (daemon program smtpd(8)).

I made the change but I'm not sure what I'm getting is of much help. I see the HELO message but it appears to be going to smtp.yahoo.com. However the relay error is smtp.gmail.com. I'm confused about what is happening. It seems to me that the HELO should be going to gmail.com base on the sasl_passwd setting.

2026-02-05T10:30:07.636948-05:00 dap002 postfix/smtp[164874]: > smtp.att.yahoo.com[66.218.88.163]:587: EHLO home.myisp.net 2026-02-05T10:30:07.671853-05:00 dap002 postfix/smtp[164871]: private/bounce socket: wanted attribute: status 2026-02-05T10:30:07.672160-05:00 dap002 postfix/smtp[164871]: input attribute name: status 2026-02-05T10:30:07.672307-05:00 dap002 postfix/smtp[164871]: input attribute value: 0 2026-02-05T10:30:07.672507-05:00 dap002 postfix/smtp[164871]: private/bounce socket: wanted attribute: (list terminator) 2026-02-05T10:30:07.672640-05:00 dap002 postfix/smtp[164871]: input attribute name: (end) 2026-02-05T10:30:07.672788-05:00 dap002 postfix/smtp[164871]: 0DFC3500071: to=<[email protected]>, relay=smtp .gmail.com[74.125.21.108]:587, delay=0.47, delays=0.16/0.13/0.14/0.04, dsn=5.7.0, status=bounced (host smtp.gmail.com[74 .125.21.108] said: 530-5.7.0 Authentication Required. For more information, go to 530 5.7.0  https://support.google.com/ accounts/troubleshooter/2402620. 00721157ae682-794fefa6448sm48418127b3.37 - gsmtp (in reply to MAIL FROM command))

Is it possible it is using [email protected] as the login rather than [email protected] which should be the from address?

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