Hi,

I have a Microsoft account and I can tell you that if you wish to report a 
fault positive Spam you have to send an email to Microsoft with the attached 
false positive email. Only Microsoft 365 customers can send these reports. They 
also give you a “report” button on their web Mail platform. As I see it, 
Microsoft will always maintain a strong hold on running an Email Enterprise 
their way.

https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/troubleshooting-mail-sent-to-office-365?view=o365-worldwide
 
<https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/troubleshooting-mail-sent-to-office-365?view=o365-worldwide>

Maybe a third party relay is the answer. 

Antonino Sidoti




> On 4 Jun 2021, at 7:42 pm, Maarten de Vries <[email protected]> wrote:
> 
> 
> On 04-06-2021 10:39, Nick Ryan wrote:
>> I have this as well, I think it's Sender Reputation too - they use 
>> Senderscore and I know my mailservers don't send enough mails to get a 
>> rating. 
>> 
>> Oddly, I have no problems sending to the free hotmail & outlook addresses. 
>> 
>> I don't have a solution apart from maybe sending through a 3rd party like 
>> Mailgun or Sendgrid. Sendgrid does have a limited (100 emails a day) free 
>> tier. 
>> 
>> Regards - Nick 
>> 
>> On 04/06/2021 05:27, Antonino Sidoti wrote: 
>>> Hi, 
>>> 
>>> I have two OpenSMTPD servers (Sydney, Tokyo) and they are both 
>>> configured with correct DNS, PTR, DKIM, SPF, MTA-STS and Dmarc. I have 
>>> no problems sending mail to Google but with Microsoft 365 (Exchange 
>>> Online) when I send an email it always end up in Junk on the receivers 
>>> side. 
>>> 
>>> I know Microsoft may be doing some strange stuff but does anyone else 
>>> have this issue. I have a valid Microsoft 365 Email Account for my day 
>>> job and from my testing it always end up in Junk when I send mail from 
>>> my OpenSMTPD servers. The raw headers don’t say much on the Microsoft 
>>> side other than it gets SCL=5, nothing else as to why it is treated as 
>>> Junk. 
>>> 
>>> I also know of other people who have Microsoft 365 Email Accounts that 
>>> all my mail ends up in their Junk too. Can’t work this out. 
>>> 
>>> Any suggestions or tips would be appreciated. 
>>> 
>>> Thanks 
>>> Nino 
>> 
> 
> I have exactly the same problem. I even went through the hoops of signing a 
> digital contract with Microsoft that I'm not sending spam (multiple times), 
> but it does not help. I also signed up for their Junk Email Reporting 
> Program, but I've never received a single complaint or notification. They 
> don't even send DMARC reports.
> 
> Eventually, I decided to use an external mail relay, because I really need my 
> email to arrive. I'm self-employed, my income depends on it. I'm still angry 
> over this though :/
> 
> I'm not 100% convinced it's the IP score though. Microsoft adds a header with 
> some spam check results. In my case, the header indicated no IP related score 
> for mail sent directly to Microsoft, or mail sent through the relay. But the 
> mail from the relay is not junked.
> 
> To be specific, the `X-Forefront-Antispam-Report` header contained 'IPV:NLI' 
> in both cases. According to Microsoft, that means the IP has no associated 
> score [1]. Then again, maybe that header isn't complete. The relay certainly 
> sends a lot more mail than me on my own.
> 
> Microsoft seems to be extremely aggressive against independent mail servers, 
> and they represent a large amount of inboxes. I wish I had a better solution 
> than paying someone else to relay your mail, with all associated security 
> risks that it brings.
> 
> 
> [1] 
> https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/anti-spam-message-headers
>  
> <https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/anti-spam-message-headers>
> 
> Regards,
> 
> Maarten
> 
> 
> 

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