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.
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|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.
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||[1] https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/anti-spam-message-headers||

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||Regards,||

||Maarten||

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