Mail server issue?

I’m using Amazon SES with the SMTP relay, and to the majority of email addresses, things work fine. I can receive email and I can send email. However recently I’ve been trying to email between myself and a Government agency about some work-related issues.

If I have the email address on Gmail using the Gmail “Send mail as” feature and send them an email, they receive it. However, if I send the exact same thing from Outlook, it doesn’t go through.

I’ve sent them multiple tests and they’ve only replied to the ones from my Gmail account. I don’t know what is causing the issue? Could their IP have been added to a blacklist of mine? Could I be blacklisted from them? Is my server blocking email going out from Outlook?

I want to rule out that my server is a problem before I enquire from them.

Check /var/log/exim4/mainlog

I know there is an issue with relay and forwarders so this might also be the issue

2022-06-09 12:55:42 1nzFpG-000BjS-Hb <= [email protected] H=mail-ej1-f41.google.com [209.85.218.41] P=esmtpsa X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_128_GCM:128 CV=no SNI=myservershostname.tld A=dovecot_plain:[email protected] K S=95457 [email protected]l.com
2022-06-09 12:55:43 1nzFpG-000BjS-Hb => [email protected] <[email protected]> R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.168.49.244] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b0181481b0a47-18e19304-8fa0-4d5b-ad13-cd0fd89168ae-000000"
2022-06-09 12:55:43 1nzFpG-000BjS-Hb Completed

2022-06-08 10:18:41 1nyqtN-00GoAI-Ly <= [email protected] H=(DESKTOPGE1MT1G) [105.184.34.189] P=esmtpsa X=TLS1.2:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no SNI=myservershostname.tld A=dovecot_login:[email protected] S=2235005 id=!&!AAAAAAAAAAAuAAAAAAAAAEh0fTJ8V+dHiE39vco3Ds8BANlTnCJhprtFudq2LHCBs8EBACQA//[email protected]
2022-06-08 10:18:42 1nyqtN-00GoAI-Ly => [email protected] R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.134.184.144] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b01814264ecc4-bfb939ef-da86-4d6b-8289-a9a64596f726-000000"
2022-06-08 10:18:42 1nyqtN-00GoAI-Ly Completed

2022-06-08 12:31:09 1nysxx-00Guf0-9j <= [email protected] H=mail-ej1-f47.google.com [209.85.218.47] P=esmtpsa X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_128_GCM:128 CV=no SNI=myservershostname.tld A=dovecot_plain:[email protected] K S=1602 [email protected]l.com
2022-06-08 12:31:10 1nysxx-00Guf0-9j => [email protected] <[email protected]> R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.134.184.144] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b018142de33b1-bc90632f-9463-4ff5-9814-ec7b1b8de7a5-000000"
2022-06-08 12:31:10 1nysxx-00Guf0-9j Completed

2022-06-08 12:39:29 1nyt5y-00Guvk-QL <= [email protected] H=securemail-y34.synaq.com [196.35.198.52] P=esmtps X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no S=10403 [email protected]ld
2022-06-08 12:39:29 1nyt5y-00Guvk-QL => info <[email protected]> R=localuser T=local_delivery
2022-06-08 12:39:29 1nyt5y-00Guvk-QL Completed

2022-06-08 13:20:11 1nytj4-00GwGN-Ef <= [email protected] H=([10.0.0.3]) [105.184.34.189] P=esmtpsa X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_128_GCM:128 CV=no SNI=myservershostname.tld A=dovecot_plain:[email protected] S=2207316 [email protected]
2022-06-08 13:20:12 1nytj4-00GwGN-Ef => [email protected] R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.168.49.244] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b0181430b193e-053fb6c5-13b4-444d-837a-378e96e3f4a0-000000"
2022-06-08 13:20:12 1nytj4-00GwGN-Ef Completed

2022-06-08 14:12:28 1nyuY0-00Gy7Y-2f <= [email protected] H=mail-ej1-f53.google.com [209.85.218.53] P=esmtpsa X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_128_GCM:128 CV=no SNI=myservershostname.tld A=dovecot_plain:[email protected] K S=2206459 [email protected]l.com
2022-06-08 14:12:29 1nyuY0-00Gy7Y-2f => [email protected] R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.168.49.244] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b0181433af634-8da47373-bc61-422e-ae80-07ac3989685c-000000"
2022-06-08 14:12:29 1nyuY0-00Gy7Y-2f Completed

2022-06-08 14:17:02 1nyucN-00GyGJ-Oh <= [email protected] H=securemail-y32.synaq.com [196.35.198.46] P=esmtps X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no S=5691 [email protected]
2022-06-08 14:17:02 1nyucN-00GyGJ-Oh => info <[email protected]> R=localuser T=local_delivery
2022-06-08 14:17:02 1nyucN-00GyGJ-Oh Completed

2022-06-08 14:17:56 1nyudH-00GyHK-2b <= [email protected] H=securemail-y60.synaq.com [196.35.198.123] P=esmtps X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no S=110157 [email protected]ld
2022-06-08 14:17:56 1nyudH-00GyHK-2b => info <[email protected]> R=localuser T=local_delivery
2022-06-08 14:17:56 1nyudH-00GyHK-2b Completed

2022-06-07 09:02:23 1nyTE2-00Fqap-UA <= [email protected] H=(DESKTOPGE1MT1G) [105.187.47.249] P=esmtpsa X=TLS1.2:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no SNI=myservershostname.tld A=dovecot_login:[email protected] S=2230724 [email protected]
2022-06-07 09:02:24 1nyTE2-00Fqap-UA => [email protected] R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.132.230.51] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b01813cf8b9c0-e6c8ea04-6854-41bf-934d-619ddf4bcc28-000000"
2022-06-07 09:02:24 1nyTE2-00Fqap-UA Completed

2022-06-07 15:45:06 1nyZVd-00G4dH-43 <= [email protected] H=(DESKTOPGE1MT1G) [105.187.47.249] P=esmtpsa X=TLS1.2:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no SNI=myservershostname.tld A=dovecot_login:[email protected] S=2215191 [email protected]
2022-06-07 15:45:06 1nyZVd-00G4dH-43 => [email protected] R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.132.230.51] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b01813e6968eb-5d30a951-a762-446e-bdab-2b55063c7094-000000"
2022-06-07 15:45:06 1nyZVd-00G4dH-43 Completed

2022-06-06 17:10:19 1nyEMf-00FFp5-SR <= [email protected] H=(DESKTOPGE1MT1G) [105.224.255.140] P=esmtpsa X=TLS1.2:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no SNI=myservershostname.tld A=dovecot_login:[email protected] S=2233712 [email protected]
2022-06-06 17:10:20 1nyEMf-00FFp5-SR => [email protected] R=send_via_smtp_relay T=smtp_relay_smtp H=email-smtp.eu-west-2.amazonaws.com [18.168.49.244] X=TLS1.2:ECDHE_SECP256R1__RSA_SHA256__AES_256_GCM:256 CV=yes A=smtp_relay_login C="250 Ok 010b0181399115b3-b5533227-4dcf-4923-8a66-b45094ef4220-000000"
2022-06-06 17:10:20 1nyEMf-00FFp5-SR Completed

Pastebin link

I did “exigrep “theirdomainname.tld” mainlog*” to find just the ones with them and they’ve all shown as completed.

I don’t see anything strange.

This is the exact problem I’m facing. Why is it just blocking on Outlook? It seems to be just on email clients that it isn’t going through. Because I’ve tried Thunderbird too.

Although I’m not using Amazon SES, one of my clients had a similar issue on Outlook 2016. Did you try renewing the profile within Outlook and playing around with different ports? Which version of Outlook are you using and with what exact settings?

I tried that and it wasn’t that.

Turns out that the receiving server does not receive email on port 465 and only accepts 587 which is very weird. So once I changed it to 587, they received the email. I don’t mind using that port since it’s the more modern one (I believe?)