On 23/01/2026 15:57, Dennis Putnam via Postfix-users wrote:
On 1/23/2026 3:21 AM, John Fawcett via Postfix-users wrote:

On 22/01/2026 21:07, Dennis Putnam via Postfix-users wrote:
On 1/22/2026 1:19 PM, Wietse Venema via Postfix-users wrote:
Dennis Putnam via Postfix-users:
Hi John,

Thanks for the reply. I thought I did what was documented but it does not work for me. Authentication fails. The same authentication works
if I don't use like originally posted:

smtp_sender_dependent_authentication = yes
I replied to that, and asked you to send "postconf -nf"
output, instead of sending a very large main.cf file.

    Wietse
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I didn't get that request. Here is the postconf -nf:

alias_database = hash:/etc/postfix/aliases
alias_maps = hash:/etc/postfix/aliases
bounce_notice_recipient = dap
command_directory = /usr/sbin
compatibility_level = 3.6
daemon_directory = /usr/lib/postfix/sbin
data_directory = /var/lib/postfix
debug_peer_level = 2
debug_peer_list =
debugger_command = PATH=/bin:/usr/bin:/usr/local/bin; (strace -p $process_id    2>&1 | logger -p mail.info) & sleep 5
defer_transports =
good_senders_only = check_sender_access hash:/etc/postfix/restricted_senders,    permit
html_directory = no
inet_interfaces = all
inet_protocols = all
local_recipient_maps = hash:/opt/mailman/mm/var/data/postfix_lmtp
mail_owner = postfix
mailq_path = /usr/bin/mailq.postfix
manpage_directory = /usr/share/man
message_size_limit = 51200000
mydestination = $myhostname, localhost.$mydomain, localhost
mynetworks_style = host
newaliases_path = /usr/bin/newaliases.postfix
notify_classes = bounce
owner_request_special = no
queue_directory = /var/spool/postfix
readme_directory = /usr/share/doc/postfix-2.10.1/README_FILES
recipient_delimiter = +
relay_domains = hash:/opt/mailman/mm/var/data/postfix_domains
relayhost = [smtp.att.yahoo.com]:587
sample_directory = /usr/share/doc/postfix-2.10.1/samples
sender_canonical_classes = envelope_sender, header_sender
sender_dependent_relayhost_maps = hash:/etc/postfix/sender_relay
sendmail_path = /usr/sbin/sendmail.postfix
setgid_group = postdrop
smtp_generic_maps = hash:/etc/postfix/generic
smtp_header_checks = regexp:/etc/postfix/header_check
smtp_helo_name = home.myisp.net
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options =
smtp_sender_dependent_authentication = yes
smtp_tls_policy_maps = hash:/etc/postfix/tls_policy
smtp_use_tls = yes
smtpd_banner = $myhostname ESMTP $mail_name ($mail_version) (Ubuntu Linux)
smtpd_relay_restrictions = permit_mynetworks, reject
smtpd_restriction_classes = good_senders_only
syslog_name = postfix
transport_maps = hash:/opt/mailman/mm/var/data/postfix_lmtp
unknown_local_recipient_reject_code = 550

CAn you post the contents of /etc/postfix/sender_relay and /etc/postfix/sasl_passwd (you can obfuscate confidential info in a consistent way)

John

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sender_relay

[email protected]        [smtp.gmail.com]:587
[email protected]            [smtp.gmail.com]:587
[email protected]              [smtp.gmail.com]:587
[email protected]                    [smtp.gmail.com]:587

sasl_passwd

# authentications for mailman3
[smtp.gmail.com]:587            [email protected]:keystring
#[email protected]           [email protected]:keystring
#[email protected]  [email protected]:anotherkeystring
# default authentication
[smtp.myisp.com]:587        [email protected]:differentkeystring

Note that the first entry is what I have now to get it partially working. The commented strings are what I tried that does not work and gets the authentication error.

This is a tried and tested functionality, so the likelihood is that there is something in your configuration or these files that has an error. It was not obvious to me from the data posted what that could be. One thing that looks wrong is that you have [email protected] in the sasl_passwd file but it's not in the sender_relay file, although I guess that's not the cause of authentication failures. It might be worth checking the files and getting someone who you can trust with the real contents to recheck them. If there is an authentication error, then the likelihood is that the credentials are wrong. I am also hoping that your key strings don't contain any : characters and in your testing you did the steps to update the .db files and reload postfix.

Also, not sure if it is relevant, but maybe worth checking the contents of file /etc/postfix/tls_policy to see if it has some entries about these domains.

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.

John

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