This is a hilarious and informative talk from Dylan.

I enjoyed the bit toward the beginning where even the latest version of the SMTP specification says that emails that fail to send should wait 30 minutes to be retried and then tried over a course of 4-5 days.

And a clip from the description:

… the relationship between email and commerce has never been more complicated. In one sense, the utopian ideal of free, decentralised, electronic communication has come true. Email is the ultimate cross-network, cross-platform communication protocol. In another sense, it’s an arms race: mail providers and ISPs implement ever more stringent checks and policies to prevent junk mail, and if that means the occasional important message gets sent to junk by mistake, then hey, no big deal – until you’re sending out event tickets and discover that every company who uses Mimecast has decided your mail relay is sending junk. Marketing teams want beautiful, colourful, responsive emails, but their customers’ mail clients are still using a subset of HTML 3.2 that doesn’t even support CSS rules. And let’s not even get started on how you design an email when half your readers will be using “dark mode” so everything ends up on a black background.

Email is too big to change, too broken to fix… and too important to ignore.