I think he meant mails that are over 400k, not 400k mails.

We encountered a similar issue around 10 years ago, where mails over 2MB to 
Gmail timed out from various global locations. Worked fine from the US.

They did eventually fix the issue after we provided the logs and pcaps, it was 
due to some rate calculation errors and out-of-sync servers.


Graeme Slogrove

-----Original Message-----
From: mailop <mailop-boun...@mailop.org> On Behalf Of Maarten Oelering via 
mailop
Sent: Friday, 3 December 2021 6:54 AM
To: Andrew Hearn <andrew.he...@aa.net.uk>
Cc: mailop@mailop.org
Subject: Re: [mailop] Sending to google/gmail - timeouts mainly with larger 
(~400k+) emails


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Hi,

Sending 400K mailings with Exim, hats off!
With large mailings you will always see some messages failing due to various 
reasons. Even with more powerful MTAs.
I would expect that the 1000 mails are left in the queue due to the to 454 … 
over quota replies from Gmail.
Are they all connection errors? Then I would suspect a problem on your side. An 
SMTP trace could help to diagnose the issue.

Maarten,
Postmastery

> On 2 Dec 2021, at 13:50, Andrew Hearn via mailop <mailop@mailop.org> wrote:
>
> Hello,
>
> We're a UK ISP, and relay email for our customers as well as send our 
> customers emails such as invoices.
>
> We currently have about 1,000 emails queued for google accounts and these are 
> failing with a timeout, eg from exim:
>
> 2021-12-02 11:48:05 1msize-005feQ-DI H=gmail-smtp-in.l.google.com 
> [142.250.13.26] TLS error on connection (send): The TLS connection was 
> non-properly terminated.
>
> 2021-12-02 11:48:05 1msize-005feQ-DI H=gmail-smtp-in.l.google.com 
> [142.250.13.26]: SMTP timeout after sending data block (525043 bytes 
> written): Connection timed out
>
> Based on past experience, eventually, the emails may will through.
>
> This is also intermittent, as sending to my own gmail address tends to get 
> through eventually, though they do still time out once or twice before 
> eventually getting through.
>
> Generally these emails do show as SPF/DKIM/DMARC PASS in gmail.
>
> This report is rather vague, but we do have further examples, logs, pcaps.
>
> Is someone from google on this list able to help investigate this problem 
> with us please? I can pass examples and pcaps privately.
>
> Thanks!
>
> Andrew, AS20712 aa.net.uk
>
>
>
> _______________________________________________
> mailop mailing list
> mailop@mailop.org
> https://list.mailop.org/listinfo/mailop

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