[exim] Intermittent gmail SMTP failures: "Authentication Req…

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Author: Bill Brelsford
Date:  
To: Exim Users
Subject: [exim] Intermittent gmail SMTP failures: "Authentication Required"
I get a significant number of failed SMTP sessions at gmail
(smtp.gmail.com::587). Connections start the same, but fail
when exim appears to not send an AUTH LOGIN command:

TCP_FASTOPEN tcpi_unacked 2
SMTP<< 220 smtp.gmail.com ESMTP q13sm8110474pfl.210 - gsmtp
SMTP>> EHLO k2di

  SMTP<< 250-smtp.gmail.com at your service, [68.186.2.255]
         250-SIZE 35882577
         250-8BITMIME
         250-STARTTLS
         250-ENHANCEDSTATUSCODES
         250-PIPELINING
         250-CHUNKING
         250 SMTPUTF8

SMTP>> STARTTLS

SMTP<< 220 2.0.0 Ready to start TLS
SMTP>> EHLO k2di

  SMTP<< 250-smtp.gmail.com at your service, [68.186.2.255]
         250-SIZE 35882577
         250-8BITMIME
         250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
         250-ENHANCEDSTATUSCODES
         250-PIPELINING
         250-CHUNKING
         250 SMTPUTF8


=== succeeds ===
SMTP>> AUTH LOGIN

SMTP<< 334 VXNlcm5hbWU6
SMTP>> ****************************

SMTP<< 334 UGFzc3dvcmQ6
SMTP>> ************************

SMTP<< 235 2.7.0 Accepted
SMTP>> MAIL FROM:<gnxl@???> SIZE=1243 AUTH=abc@xyz
SMTP>> RCPT TO:<wymby@???>

         will write message using CHUNKING

SMTP>> BDAT 243 LAST

SMTP<< 250 2.1.0 OK k9sm14509820pgg.50 - gsmtp
SMTP<< 250 2.1.5 OK k9sm14509820pgg.50 - gsmtp
SMTP<< 250 2.0.0 OK k9sm14509820pgg.50 - gsmtp
SMTP>> QUIT


=== fails ===
SMTP>> MAIL FROM:<gnxl@???> SIZE=1243
SMTP>> RCPT TO:<wymby@???>

         will write message using CHUNKING

SMTP>> BDAT 243 LAST

  SMTP<< 530-5.7.0 Authentication Required. Learn more at
         530 5.7.0  https://support.google.com/mail/?p=WantAuthError q13sm811047=>4pfl.210 - gsmtp
  SMTP<< 530-5.7.0 Authentication Required. Learn more at
         530 5.7.0  https://support.google.com/mail/?p=WantAuthError q13sm8110474pfl.210 - gsmtp

SMTP>> QUIT


Failures happen with both of my gmail accounts. They seem to
be random; repeated identical attempts are unpredictable, and
it doesn't matter which gmail server IP address I'm connected
to. The transport's hosts_require_auth includes smtp.gmail.com.
I don't have the problem with (several) non-gmail servers.

I'm running 4.94.2-7 on Debian 11.2, and 4.95-4 on Debian sid.

Suggestions? Thanks.