What kind of mail are you sending? Are you getting anything on your abuse@ address? Are you getting any feedback on JMRP [0]? If all else fails, the mailop mailing list [1] can get you closer to someone on one of these networks to help.
>There is also no way to get their attention for this issue, as they simply don't reply to complaints about that. How to solve issues like that?
At one point, after getting one-too-many rejections for a particular recipient, I started sending the postmaster of the recipient’s service an email every time I needed to contact the recipient. That resolved the issue pretty quickly. You can always try annoying the postmaster.
Just personal emails. Volume would be somewhere around one email per month or so.
> Are you getting anything on your abuse@ address?
Nope.
> Are you getting any feedback on JMRP [0]?
That seems to require a Microsoft account and that's something I neither have nor want. I believe sending emails has to work without having to register an account for each provider you're interacting with.
> If all else fails, the mailop mailing list [1] can get you closer to someone on one of these networks to help.
Thanks for the tip, although I'm not sure if I'm the right audience for this list, as I just run a personal mail server with very low volume.
> If you want to send mail to recipients who have accounts at big email providers, be aware that all of the above cannot guarantee that these providers won’t reject your mail, put it straight into recipient’s spam folder or just silently discard it - they just impose their own rules on anyone and you virtually can’t do anything about it.
My guess is, that the reason for the problems is the same as quoted in another comment (https://news.ycombinator.com/item?id=29673347), stating that the mail volume is just too low for outlook.com to establish enough trust in the sending mail server.
If you look around on the internet, there are plenty of other people with the same issues with outlook.com. To me it seems Microsoft is doing something fundamentally hostile to small mail servers there. Interestingly enough sending to Office 365 hosted email addresses works just fine.
>That seems to require a Microsoft account and that's something I neither have nor want. I believe sending emails has to work without having to register an account for each provider you're interacting with.
Yes it does require signing up with them. I see that you’re taking a moral stance on this so I guess the best action is to just ask people to not use Microsoft email products, which is perfectly reasonable in my opinion.
For what it’s worth, I do have an account with them and I am very small scale and don’t have any deliverability issues with Microsoft.
>There is also no way to get their attention for this issue, as they simply don't reply to complaints about that. How to solve issues like that?
At one point, after getting one-too-many rejections for a particular recipient, I started sending the postmaster of the recipient’s service an email every time I needed to contact the recipient. That resolved the issue pretty quickly. You can always try annoying the postmaster.
[0]: https://postmaster.live.com/snds/JMRP.aspx
[1]: https://www.mailop.org/