We've been having delivery issues to gmail since November 15 at 12:17 pm 
(Central).  But there's still lots of email going through, too.

Here's an example from our mail server's logs:

Failed <snip> rr=Site gmail.com (2607:f8b0:4001:c5a::1a) said after data sent: 
550 5.7.1  https://support.google.com/mail/?p=NotAuthorizedError 
75-20020a6b144e000000b007a2a17ef77bsi3551757iou.146 - gsmtp 550-5.7.1 
[2607:fe28:0:4000::10] The IP you're using to send mail is not\n550-5.7.1 
authorized to send email directly to our servers. Please use the 
SMTP\n550-5.7.1 relay at your service provider instead. Learn"

What's interesting is that all the failure come from our email server's IPv6 
address, which has been in place for 5+ years and matching FQDN and PTR.

Frank 

-----Original Message-----
From: mailop <[email protected]> On Behalf Of Omar Thameen via mailop
Sent: Wednesday, November 15, 2023 11:50 AM
To: [email protected]
Subject: [mailop] Gmail deferrals resolved by transit encryption

This might be old news, but we started seeing delivery deferrals
to Gmail starting Nov 13 around 4pm EST.  It started at about 10%
of deliveries, mostly affecting larger accounts, and all having IP
and domain reputations in Google Postmaster Tools of high and medium.
Messages were delivered on subsequent retries.

Last night, when the deferrals increased to 25-30%, we deployed TLS
for deliveries, and the deferrals immediately went to zero.

Hope that helps others.

Omar
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