Ever since Microslop, 'xcuse me, Microsoft entered the AI age, the quality went downhill. Someone should analyse this objectively since right now this may be more of an impression. But people are noticeably angrier than they used to be about Microsoft, say, 5 years ago, to today.
Why do you feel the need to pollute HN with terrible slashdot jokes?
To be fair, Outlook.com has always been a bit shitty, if you're trying to deliver email to them. Last time it was reasonably good the service was still called Hotmail.
The problem is that we've allowed email to be centralized around a few massive providers, who do not care about customer service. If you're large enough, you probably have a contact at Microsoft for Outlook. Everyone else has to yell into the void and sometimes that works.