So, I don't really know where to start, Microsoft has really started to frustrate me with all their email stupidity. Their "spam filters" usually let go most of the spam which reaches our inbox but legitimate email sent from a self hosted email system (like our 91mail:mailcow-dockerized) are usually rejected or if somehow delivered, always land in spam. We've tried contacting Microsoft multiple times, they always have the several times over the last few years with the same response that we've received: "this IP address doesn't qualify for mitigation" this comes as a first & final reply and no matter how many times we reply to the email requesting a manual review of the situation, despite our IPs having a clean record and not being listed on any of the email blacklists, they still refuse to accept our emails in their system. The situation keeps on getting worse with each day, we had to finally choose to relay our emails going to outlook and such domains through a 3rd party service (AWS-SES in our case) just like many other self-hosters whose prayers to microsoft's support go unanswered, We don't want to subscribe to their expensive outlook subscriptions, we have our own servers which we use to host email systems and we use the same for our internal communication along with interaction to public facing services. This also includes client communication but all in vain, microsoft would continue to ignore our pleas and we will have to continue to figure out ways to deliver our email to customers who really expect to receive our emails in their inbox and not go hunting for spam everytime they expect a communication from their service provider.
This is a companion discussion topic for the original entry at https://www.tekduke.com/rant-why-i-hate-outlook/