Same experience here. We have multiple customers whose servers are in large blocked IP ranges, with seemingly no way to get them delisted. The strange thing is that Microsoft only seems to reject their emails on Hotmail/Outlook.com accounts (free accounts), while accepting them just fine on business accounts. Meanwhile, their “support” tools tell you there’s nothing wrong.
Based on my broad experience, I’d comfortably rank Microsoft as the worst of the major email providers. (I am owner poste.io)
I work at a big company that sends alot of emails. And even we have been put in the "bad bad books of o365 bad list", it's an absolute pain to get yourself out of the office 365 defender (I think it's what they call it now?) meanwhile your customers are complaining they arent receiving emails from you.
Are companies like MailChimp, SendGrid, etc affected the same way?
Yes. I once had issues with emails being rejected by Outlook on MailGun. And it was only Outlook. Had to contact support, they promptly changed my account to another server/IP once I mentioned it was Outlook, sounded like a recurring issue.
Well, your big company should then call M$ out then. E.g., consider you're sending a confirmation e-mail during account registration, then when your server detects that relay is `*.oulook.com` show a warning: 'outlook users most probably will not receive emails from us due to bs policy at microsoft. consider using a different email provider.'
Yes, that may turn some users away, but they would complain and leave anyway, because they don't receive emails from your server. On the other hand, that's how one can contribute to unwinding ms's share of email accounts.
Think about what you're saying: someone is near the top of the sales funnel and despite the odds you've convinced them to provide their email so you can start the process of trying to convert. Even if you are good you'll still lose 80% of people from this point before you see a single dollar. Now, inject some extra weird, sketchy-sounding friction AND ask them to change their email provider, something 99% of employees never think about let alone control. Not sure how old you are but you'd have better luck convincing users "this site works best in IE4".
Right, letting users frustrate silently, without explaining to them why they don't receive correspondence is the way to go. Discussing my age/gender/race isn't productive either. Dont rage, just pay attention to what's written. I only suggest them to select a different e-mail for better experience, not reqiring it. And the actual wording of this suggestion should always be developed in collaboration with company's layers and marketing teams.
Email delivery for enterprise accounts has always been more lenient, the assumption being that enterprises do have their own mail filtering software.