You could try some of the options listed here for troubleshooting: https://learn.microsoft.com/en-us/exchange/troubleshoot/email-delivery/email-delivery-issues

Best,
Attila

On Thu, Nov 2, 2023 at 4:37 PM Mat Kowalski via swinog - swinog at lists.swinog.ch <swinog_at_lists_swinog_ch_tpveugmui@simplelogin.co> wrote:
And I realized it's silly to hide domains, so here it goes

* sender domain - kowalski.xyz
* recipient domain where the problem was first observed - amag.ch
* my 2nd domain which reproduces the problem - microsoft365.kowalski.xyz

Cheers!

On 02/11/2023 16:17, Mat Kowalski wrote:
> Hi all,
>
> I wonder if someone could point me in a correct direction for debugging mails between Proton and Outlook landing in spam... What happens is
>
> * my domain XXX plugged to mail.protonmail.ch.
> * my 2nd domain YYY plugged to mail.protection.outlook.com.
> * every mail sent from Proton to Outlook lands in spam
> * headers as seen by Outlook indicate SCL score 5
>
> The content I use for the test is not anything synthetic but a real message. In the headers I can also see that the "basic configuration" is correct, i.e.
>
> * SPF passed
> * DKIM passed
> * DMARC passed
>
> so this gives no useful information sadly. Maybe someone here has experience with debugging Microsoft? The issue is that this makes my private mailbox unusable as whoever out there uses Outlook as their mail service is not getting my emails. Quite sick...
>
> Thanks a lot for any help,
> Mateusz

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