Closed
Description
Describe the bug
Whenever somebody from microsoft outlook (doesn't matter if it's company, or private email) tries to send me a message, the message delivery fails. Funnily enough, I can send mail no problem to outlook addresses. Any other host can send my maddy server messages without a single problem, I have tried at least twenty.
Steps to reproduce
Send a message from an outlook address to the maddy server.
Log files
When outlook connects to my server:
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 220 redacted ESMTP Service Ready
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: EHLO EUR05-DB8-obe.outbound.protection.outlook.com
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-Hello EUR05-DB8-obe.outbound.protection.outlook.com
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-PIPELINING
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-8BITMIME
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-ENHANCEDSTATUSCODES
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-CHUNKING
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-STARTTLS
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250-SMTPUTF8
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 250 SIZE 67108864
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: STARTTLS
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 220 2.0.0 Ready to start TLS
Nov 02 16:17:04 tempelhof maddy[81396]: smtp: 550 5.0.0 Handshake error
The logs that outlook gave me after it couldn't deliver:
Diagnostic information for administrators:
Generating server: AM7PR10MB3480.EURPRD10.PROD.OUTLOOK.COM
Receiving server: AM7PR10MB3480.EURPRD10.PROD.OUTLOOK.COM
redacted@redacted.tld
11/2/2024 9:26:59 AM - Server at AM7PR10MB3480.EURPRD10.PROD.OUTLOOK.COM returned '550 5.4.317 Message expired, cannot connect to remote server(451 4.4.0 Security status Renegotiate)'
11/2/2024 9:17:03 AM - Server at redacted (redacted) returned '450 4.4.317 Cannot connect to remote server [Message=451 4.4.0 Security status Renegotiate] [LastAttemptedServerName=redacted] [LastAttemptedIP=redacted] [SmtpSecurity=-2;-2] [DB8EUR05FT024.eop-eur05.prod.protection.outlook.com 2024-11-02T09:17:04.213Z 08DCFA5EB073BFF6](451 4.4.0 Security status Renegotiate)'
Original message headers:
Received: from PAVPR10MB7354.EURPRD10.PROD.OUTLOOK.COM (2603:10a6:102:31d::12)
by AM7PR10MB3480.EURPRD10.PROD.OUTLOOK.COM (2603:10a6:20b:132::17) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.8114.20; Sat, 2 Nov
2024 07:32:55 +0000
---snip---
Configuration file
TLS config:
protocols tls1.2 tls1.3
ciphers ECDHE-ECDSA-WITH-AES256-GCM-SHA384 ECDHE-ECDSA-WITH-CHACHA20-POLY1305 ECDHE-ECDSA-WITH-AES128-GCM-SHA256 ECDHE-RSA-WITH-AES256-GCM-SHA384 ECDHE-RSA-WITH-CHACHA20-POLY1305 ECDHE-RSA-WITH-AES128-GCM-SHA256
I also tried with:
protocols tls1.0 tls1.3
ciphers RSA-WITH-RC4128-SHA RSA-WITH-3DES-EDE-CBC-SHA RSA-WITH-AES128-CBC-SHA RSA-WITH-AES256-CBC-SHA RSA-WITH-AES128-CBC-SHA256 RSA-WITH-AES128-GCM-SHA256 RSA-WITH-AES256-GCM-SHA384 ECDHE-ECDSA-WITH-RC4128-SHA ECDHE-ECDSA-WITH-AES128-CBC-SHA ECDHE-ECDSA-WITH-AES256-CBC-SHA ECDHE-RSA-WITH-RC4128-SHA ECDHE-RSA-WITH-3DES-EDE-CBC-SHA ECDHE-RSA-WITH-AES128-CBC-SHA ECDHE-RSA-WITH-AES256-CBC-SHA ECDHE-ECDSA-WITH-AES128-CBC-SHA256 ECDHE-RSA-WITH-AES128-CBC-SHA256 ECDHE-RSA-WITH-AES128-GCM-SHA256 ECDHE-ECDSA-WITH-AES128-GCM-SHA256 ECDHE-RSA-WITH-AES256-GCM-SHA384 ECDHE-ECDSA-WITH-AES256-GCM-SHA384 ECDHE-RSA-WITH-CHACHA20-POLY1305 ECDHE-ECDSA-WITH-CHACHA20-POLY1305
curves p256 p384 p521 X25519
SMTP config:
smtp tcp://${pub_ipv4}:25 tcp://[${pub_ipv6}]:25 {
debug true # only for the logs
io_debug true
limits {
all rate 20 1s
all concurrency 10
}
max_message_size 64M
check {
require_mx_record
require_tls { fail_action quarantine }
dkim
spf
rspamd {
api_path redacted
}
}
dmarc yes
source $(local_domains) {
reject 501 5.1.8 "Use Submission for outgoing SMTP"
}
default_source {
destination postmaster $(local_domains) {
deliver_to &local_routing
}
default_destination {
reject 550 5.1.1 "User doesn't exist"
}
}
}
And I also tried this with the whole check block, and dmarc commented out.
Environment information
- maddy version: 0.7.1 linux/amd64 go1.22.6
- os: NixOS 24.11 (Vicuna) (unstable)