Issue Email deliverability issues

[selsiusx]

Server operating system version

Ubuntu 20.04 x86_64

Plesk version and microupdate number

Plesk Obsidian 18.0.58.2

I have a near perfect score on mail-tester.com -> Spam Test Result

But still all the email that get sent through roundcube or thunderbird are going straight to outlook junk. I checked all the spam blacklists and the IP is clear. Also I asked for a delist with microsoft and they said I wasn't on their list...

Also RDNs etc is all okay. could it be a postfix issue ? What is happening to my genuine, not even newsletter-like or commercial, emails?

Can anyone assist? I'm losing my mind over here. Been trying to fix this for a weeks..

 

[Martin Dias]

Any header from a message that landed in spam at Outlook?

 

[selsiusx]

Any header from a message that landed in spam at Outlook?

sure!
here you go Received: from PAVPR02MB9569.eurprd02.prod.outlook.com (2603:10a6:102:305::14) - Pastebin.com

 

[Peter Debik]

Could you please provide the mail text where you believe Microsoft says you are not listed in their block lists? I am asking, because often MS responds with a text that sounds as if you are not listed or a delisting is not necessary, but then you need to reply to this mail so that a real human checks it and actually delists you.

 

[AYamshanov]

Based on pastebin and Anti-spam message headers

"SFV:SPM" - "The message was marked as spam by spam filtering",
You also could check headers with Message Header Analyzer. Unfortunately, don't see something really wrong in the headers.

 

[selsiusx]

Could you please provide the mail text where you believe Microsoft says you are not listed in their block lists? I am asking, because often MS responds with a text that sounds as if you are not listed or a delisting is not necessary, but then you need to reply to this mail so that a real human checks it and actually delists you.

Actually, it was through their delisting website. Delist IP - Delist IP
I just redid the process, so I could attach the relevant screenshots.

 

[JVG]

I've been having the same issue for years with Outlook/Hotmail. All checks are passed, no blacklisting or block listing whatsoever, and still outlook detects delivers the mails to the spam folder.

I even set up a DMARC rua tag so I can review the delivery reports. All ok, still straight to SPAM. My solution? Alert to my clients about Outlook/Hotmail delivery issues. So no real solution after all.