Re: Microsoft 365 - Mail always goes to Junk

[Antonino Sidoti]

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
 


Maybe a third party relay is the answer. 

Antonino Sidoti




> On 4 Jun 2021, at 7:42 pm, Maarten de Vries  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
>  
> 
> 
> Regards,
> 
> Maarten
> 
> 
> 

Re: Microsoft 365 - Mail always goes to Junk

[Maarten de Vries]

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||


||
||

||Regards,||

||Maarten||

||
||

Re: Microsoft 365 - Mail always goes to Junk

[Nick Ryan]

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

Re: Microsoft 365 - Mail always goes to Junk

[Jason Barbier]

Chances are it's IP reputation, who is your hosting provider?

---
GPG: https://corrupted.io/kusuriya.pub

On Thu, Jun 3, 2021, at 9:27 PM, 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
> 
> 
>