Office365 xxx.prod.outlook.com Too many recipients

stat=Deferred: 452 4.5.3 Too many recipients (AS780090)

From further research, it appears that Office 365 servers are picky with new servers, and they require them being run long enough to gain a good reputation. A lot of people complain about this. Email will often be deferred.
So I switched ip addresses for my new mal server. with another email server I have, that only sends out a small amount of email every often.
Voila. Now my new mail server has no problems with Microsoft servers. No matter how much email is sent out.

Office365 restricting new email server using sendmail. 2023

Office365のメールサーバは、新しいメールサーバに強い規制をかける?

エラーは以下の通り。
(host メールサーバー名.mail.protection.outlook.com [23.xx.xx.xx] said: 452 4.5.3 Too many recipients (xxxxxx)[xxxJPN01.prod.protection.outlook.com] (in reply to RCPT TO command))
という感じでメールキューがたまりまくる。

ニリアコットの仕事: メールサーバーのIPを変えた際に起きたoffice365の受信問題 2018

当社のメールサーバー(sendmail)のログに次の内容があり、
A社のメールサーバーは当社からのメールを一件ずつしか受領ていない様子です。

  ---ログ---
  relay=一部伏字.ction.outlook.com. [A社のメールサーバーIP],
    dsn=4.5.3, stat=Deferred: 452 4.5.3 Too many recipients (AS780090)

Redirecting 2016

I kind of lost the original thread but I think you are looking for this
solution.

In your sendmail.mc stick these in:

define(`SMTP_MAILER_MAXRCPTS', `1')dnl
define(`RELAY_MAILER_MAXRCPTS', `1')dnl

Those will make sendmail queue them out one at a time rather than bundle them
together and get that multi-domain isn't allowed error from gmail.

Been using that for a while and haven't seen a single rejection or error
dealing with them. Also works well for the idiots at protection.outlook.com
because they randomly set max nrcpts to 2.

Google "multiple destination domains" issue 2022

sendmail SMTP_MAILER_MAXRCPTS 1

define(`SMTP_MAILER_MAXRCPTS', `1')dnl

SMTP_MAILER_MAXRCPTS    [undefined] If defined, the maximum number of
                        recipients to deliver in a single envelope for the
                        smtp, smtp8, esmtp, or dsmtp mailers.

cf の Msmtp Mesmtp Msmtp8 Mdsmtp Mrelayが

Msmtp,		P=[IPC], F=mDFMuX, S=EnvFromSMTP/HdrFromSMTP, R=EnvToSMTP, E=\r\n, L=990,
		T=DNS/RFC822/SMTP,
		A=TCP $h
↓
Msmtp,		P=[IPC], F=mDFMuX, S=EnvFromSMTP/HdrFromSMTP, R=EnvToSMTP, E=\r\n, L=990,
		r=1, T=DNS/RFC822/SMTP,
		A=TCP $h

になる。

SMTP_MAILER_MAXRCPTS translates into "r" mailer field
The field has been added in sendmail-8.12.0

What release of SM provides SMTP_MAILER_MAXRCPTS

If, however, you are those that directly edit the .cf instead of the .mc then you’ll have to do the following

In you .cf find the following text (“Msmtp,” , “Mesmtp,” , “Mdsmtp, “, “Mrelay,”) After that find the following line(s)

T=DNS/RFC822/SMTP, And change it to look like this

r=1, T=DNS/RFC822/SMTP,

email - Multiple destination domains per transaction is unsupported - Stack Overflow

https://copyprogramming.com/howto/multiple-destination-domains-per-transaction-is-unsupported
は stackoverflow.com のコピー?

sendmail gmail Multiple destination domains per transaction is unsupported - external storage 1 2019

※RELAY_MAILER_MAXRCPTS は設定してもcfに変更なし (sendmail 8.17.2) → 不要?

sendmail QUEUE_GROUP r=1

I'm reluctant to break a fundamental optimization in email delivery to
work around google's behavior. Although perhaps on today's
infrastructure it wouldn't really make all that much of difference.

https://groups.google.com/g/comp.mail.sendmail/c/hAXDLGJPeM4

SMTP_MAILER_MAXRCPTS ではなく QUEUE_GROUP で対処する

local.domain.com.mc

QUEUE_GROUP(`local',  `P=/var/spool/mqueue/local')dnl
QUEUE_GROUP(`remote', `P=/var/spool/mqueue/remote, r=1')dnl

LOCAL_RULESETS
Squeuegroup
R$* @ local.domain	$# local
R$* @ $*		$# remote

mkdir /var/spool/mqueue/local
mkdir /var/spool/mqueue/remote

$ mailq
/var/spool/mqueue is empty
/var/spool/mqueue/local is empty
/var/spool/mqueue/remote is empty
		Total requests: 0

/var/log/maillog
41D2uAov090715: split: maxrcpts=1, rcpts=3, count=2, ids=41D2uAow090715; 41D2uAox090715
41D2uAou090715: split: count=1, id=41D2uAov090715

@local.domain 以外はr=1