outlook.com and O365 are horrible to deliver to. We regularly get issues where we sent an email it was accepted by O365 but was never delivered to the mailbox. We have one person working at least half the time on resolving stuff like that. And that's from a respectably maintained SES egress with good reputation, DMARC, DKIM configured.

> Outlook.com and similar are an anathema to email. This is why they tell you not to run a mail server .

It turns out that whoever has the most power is the most powerful. This is why distributed/decentralized systems cannot singlehandedly free us from tyranny, and why I find people who spend all their time preaching decentralized systems to be quite silly. We don't need better systems (well maybe we do but,,,), we need better education and awareness of how billionaires manipulate us; this goes beyond software.

Just put codex in a continuous goal loop to keep you off the blacklists...give it whatever email / creds it needs to make the appropriate requests and make the needed changes (ofc tell it the guardrails it should follow).

Selfhosted email is likely easier now than it ever was before.

Using self hosted email service is a big mistake in 2026.

I was viciously mean in my communication with the Outlook team when they said they “couldn’t” remove me from the blocklist. I pointed out that, as the operator of a perfectly compliant secure server their inability to deliver my mail is a technical failure on their end and one which I will be contacting their supervisor about and they somehow managed to scrabble together the heroic ability to delete my row from a table. Never back down from these bastards.

Maybe don't self-host mail on a shitty $1/month VPS where 99% of the tenants are spammer scum?

This is not Microsoft's fault. The building's on fire and they're locking out the arsonists.