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 <[email protected]> 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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