On Wed, Jul 10, 2024 at 11:06:06AM +0200, Fourhundred Thecat via Postfix-users 
wrote:

> I sent an email with one "to" and one "cc", and in the logs, I see:
> 
>   host said: 452 4.5.3 Too many recipients
> 
> but the next line says:
> 
>   Queued mail for delivery
> 
> 
> 2024-07-10 10:20:56  postfix/smtp: Untrusted TLS connection established to
> canadianmanganese-com.mail.protection.outlook.com[52.101.190.1]:25:
> TLSv1.3 with cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange
> ECDHE (P-384) server-signature RSA-PSS (2048 bits) server-digest SHA256

A TLS handshake completed for a connection to 52.101.190.1 on port 25.

> 2024-07-10 10:20:56  postfix/smtp: AF00FF1: host
> canadianmanganese-com.mail.protection.outlook.com[52.101.190.1] said:
> 452 4.5.3 Too many recipients (AS780090)
> [YT2PEPF000001CC.CANPRD01.PROD.OUTLOOK.COM 2024-07-10T08:20:56.830Z
> 08DC9E0156AD0174] (in reply to RCPT TO command)

One of the message recipients was deferred (4XX error code) by that
server.

> 2024-07-10 10:20:57  postfix/smtp: AF00FF1:
> to=<[email protected]>,
> relay=canadianmanganese-com.mail.protection.outlook.com[52.101.190.1]:25,
> delay=2.1, delays=0.02/0.02/0.91/1.2, dsn=2.6.0, status=sent (250 2.6.0
> <[email protected]>
> [InternalId=29463475654302,
> Hostname=YT1PR01MB8153.CANPRD01.PROD.OUTLOOK.COM] 13353 bytes in 0.132,
> 98.780 KB/sec Queued mail for delivery)

But one (presumably the first) was delivered.  So the server in question
was only willing to accept one recipient at a time.

> 2024-07-10 10:20:58  postfix/smtp: Untrusted TLS connection
> established to > 
> canadianmanganese-com.mail.protection.outlook.com[52.101.192.0]:25:
> TLSv1.3 with cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange
> ECDHE (P-384) server-signature RSA-PSS (2048 bits) server-digest SHA256

A second TLS handshake completed for a [new] connection to 52.101.192.0
on port 25.  This is another IP address of some MX host for the
destination domain.

> 2024-07-10 10:21:00  postfix/smtp: AF00FF1:
> to=<[email protected]>,
> relay=canadianmanganese-com.mail.protection.outlook.com[52.101.192.0]:25,
> delay=4.7, delays=0.02/0.02/3/1.6, dsn=2.6.0, status=sent (250 2.6.0
> <[email protected]>
> [InternalId=29390461210327,
> Hostname=YQBPR0101MB8558.CANPRD01.PROD.OUTLOOK.COM] 13403 bytes in
> 0.165, 78.890 KB/sec Queued mail for delivery)

The remaining (2nd) recipient was delivered via this second connection.

> 2024-07-10 10:21:00  postfix/qmgr:      AF00FF1: removed

Both recipients were delivered, and the message removed from the queue.

> what exactly is going on, and was my email delivered to both recipients?

See above.  Nothing unusual was going on, one of the recipients required
trying another MX host.

Ignore the other misguided response to your post.

-- 
    Viktor.
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