On 04/12/2024 3:49 am, Wietse Venema via Postfix-users wrote:
Viktor Dukhovni via Postfix-users:
> Trusted TLS - so I think that proves my SSL is good?

No, that means they presented a client certificate for no particularly
good reason, one that happened to chain up to a known trust anchor.

This reason:

smtpd_tls_ask_ccert = yes

Not sure why I set that ever - I've had it there for a long time though.
I have disabled it and it hasn't made any difference.


But it hangs up after EHLO-STARTTLS-EHLO. Something it does not like
after the (second) EHLO response?

        Wietse

Yes, I've even tried filtering out a few EHLO messages using postfix, but still the same behaviour from Microsoft/Outlook/365.

To answer Viktor's question "Are there failures from other sources within "outbound.protection.outlook.com"?" - Yes, every attempt from *.outbound.protection.outlook.com is failing:

postfix/smtpd[15735]: lost connection after EHLO from mail-australiasoutheastazon11020092.outbound.protection.outlook.com[52.101.152.92] postfix/smtpd[15717]: lost connection after EHLO from mail-psaapc01on2110.outbound.protection.outlook.com[40.107.255.110] postfix/smtpd[15826]: lost connection after EHLO from mail-australiasoutheastazon11020101.outbound.protection.outlook.com[52.101.152.101] postfix/smtpd[15826]: lost connection after EHLO from mail-tyzapc01on2112.outbound.protection.outlook.com[40.107.117.112] postfix/smtpd[15717]: lost connection after EHLO from mail-tyzapc01olkn2078.outbound.protection.outlook.com[40.92.107.78] postfix/smtpd[15826]: lost connection after EHLO from mail-tyzapc01on2111.outbound.protection.outlook.com[40.107.117.111] postfix/smtpd[16050]: lost connection after EHLO from mail-sg2apc01on2113.outbound.protection.outlook.com[40.107.215.113] postfix/smtpd[16050]: lost connection after EHLO from mail-koreacentralazon11023086.outbound.protection.outlook.com[40.107.44.86] postfix/smtpd[16050]: lost connection after EHLO from mail-australiaeastazon11022099.outbound.protection.outlook.com[40.107.40.99] postfix/smtpd[16112]: lost connection after EHLO from mail-australiaeastazon11020119.outbound.protection.outlook.com[52.101.150.119] postfix/smtpd[16050]: lost connection after EHLO from mail-psaapc01on2136.outbound.protection.outlook.com[40.107.255.136]


I have _worked around_ the problem currently by setting up a backup MX server. It runs a slightly more modern version of Postfix (3.7.11) and it seems to be happily accepting the mail from Outlook. It's an annoying workaround though, so I will go down the route of asking on the MailOPs list to see if anyone there can shed any light.

I really appreciate the help and suggestions that were offered, thank you all very much.

I will post back if I ever get a resolution to this.

Kind Regards,
Tim Harman
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