RANT: Why I hate outlook

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.

Since people like me don't want to lose their business over microsoft's weirdness, we usually give in to relaying emails to microsoft through a 3rd party service which ensures that our emails actually reach where they're supposed to be. Since starting to relay via SES, I've seen a 10x increase in email deliverability, clients now confirm that they can receive our emails in their inbox, and as we all know, a happy customer is the key to success.

I've heard some say that maybe I'm on a bad ASN, I'm not, I have confirmed this multiple times through multiple sources that The ASN/IP range allocated to our email infrastructure is clean, none of the email blacklists have ever listed the IP subnet that our service is hosted on, We've specifically requested our server provider to put us on a subnet suitable to critical emails and trust me, while sendin to any other service provider (be it Google or anything else) emails deliver to the customer inbox a 100%. never have we received a complaint forma customer of the email reaching spam or not delivering a single time. However, after 3 IP switches, 1 change of subnet and multiple requests to microsoft support, we still tend to be stuck in the same situation where any email that is sent to any @outlook.com @hotmail.com @live.com or any other MS365 hosted email account, it is guaranteed to reach spam no matter what.

This brings a lot of annoyance and seriously creates an anti-trust feeling towards microsoft where their stupid spam filters can let go of regular spam but can't let legitimate emails reach the user inbox. One rumor I've heard is that one has to regularly and continously send emails to random microsoft inboxes in order to qualify as a "NOT-SPAM" ip address, this rumor also concludes that if you continue sending random emails to microsoft addresses, they'll eventually let you through and in the same time, if your users actually receive your emails and reply, you'll get some mercy for the next couple emails unless they lose their cool once again and start blocking you for no particular reason once again.

In a perfect world, I'd see nobody using microsoft's stupid email service for this particular reason and we'd block microsoft emails from registering for our products and services because they're a nuisance to deal with. However, the world isn't perfect and people will continue to use microsoft for their emails no matter what.

So, in a conclusion, we'll have to learn to live with their narcissist behaviour and continue this cat & mouse game until one golden day where none of our customers use microsoft for their email anymore and we're all hunky dory. That'll remain to be a distant dream though. I don't see this happening because of several reasons ranging from microsoft upselling their services as bundle through many registrars, there are institutions which use microsft services and tend to subscribe to their email as well to keep the bills to a minimum and getting support from a single source. We also can't ignore that most people using windows these days use a digital license, It turns out that they also sign up to microsoft's email services to create a microsoft account to use it with microsoft's windows license. This makes this email as their default mailbox on their personal computers and whenever they have to quickly send/receive an email, they tend to give out this same email to anyone asking for it.

This lands them in a very awkward situation where some of their services use this email so gradually, they tend to move all their services to this email because it's right there in their task bar to be accessed. I've once tried to do this myself so I don't blame anyone. It just feels convenient till the day you realize that you can also sign in to other email accounts in this same app if you decide to dedicate a minute or two out of your so busy schedule. I've since then moved on from using microsoft to using my own email for 90% of the services. I still have some banking and other mission critical emails associated with microsoft because these services tend to reject domains other than @gmail.com or one of the microsoft/yahoo etc.

I see things changing though, Very recently, my bank asked us to verify our email/contact number in light of the COVID 19 outbreak and their unability to send physical statements. This time, using my aliased email (bank+not*******ons@itsbhanu*****a.com) seemed to have worked just fine, I've been able to receive my statements for the last 2 months on this alias just fine and that is true of most of my bankers (one is still reluctant to move out of free email domains) so I see the world changing. Let's just hope there is a chance where people are more sensitive towards keeping their data to themselves and microsoft starts to understand the fact that self hosted emails are important too.

Ps: redacted parts of email to prevent myself from getting spammed.

Have You ever been into a similar situation where you can't send emails to a provider? share your story with us on my discussion forum at discuss.tekduke.com