That's so frustrating. The biggest AI company in the world and their anti-spam system is so stupid? Really lowers your expectations on state of the art tech.
They're not stupid. It's part of a sophisticated long-term strategy. They deliberately make things complicated to maintain so that you give up and use their services. This strategy is working. Many small and mid-sized businesses today gave up on email maintenance altogether and outsourced it to either Google or Microsoft. Many individuals end up using Gmail, because it seems more "reliable" now that so many other people are on Gmail.
I have a similar impression from dealing with deliverability issues.
Relevant providers usually just require a few days of sending legit mail and occasionally asking to be unblocked, but there seems to be no chance getting into the inbox on GMail and Outlook with a "too low" sending volume.
If it wasn't for regulations, I would have already given up and switched to GMail.
