Email vs Capitalism, or, Why We Can't Have Nice Things
summary
A live interactive demo sends attendees emails and exposes delivery variability: RFC 5321 still allows 30 minutes to try again and up to days, yet users expect seconds. Production system sends 250,000 emails a day with 50,000/hour spikes, and relay/blacklist behavior breaks delivery. Tests across Office365, Gmail, Zoho, Proton and FastMail show inconsistent local-part handling — notably FastMail accepts quoted local parts and spaces while Google and Microsoft reject some RFC‑legal addresses. Practical fixes covered: SPF/DKIM/SPF DNS records, MJML/Foundation for HTML, Papercut and Mailtrap for dev testing, and why running your own relay gets you listed.
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chapters (26)
- 0:00Interactive email demo
- 10:31Birth of email in 1961
- 11:12ARPANET and internet foundation
- 12:38Ray Tomlinson and @ symbol
- 14:25Gary Turk and first spam
- 16:50Hippie internet flaws
- 17:32Generations and internet evolution
- 18:57SMTP success and limits
- 20:03Email address validity
- 23:32Testing corporate email
- 27:44Gmail plus addressing
- 30:31Catchall addresses
- 33:21Direct delivery quirks
- 37:07Why physical mail works
- 38:12Rise of spam and CAN-SPAM
- 41:22Authentication and SMTP security
- 44:31John Gilmore’s open relay
- 45:54Spam blacklists problems
- 47:18SPF records and auth
- 49:02Email headers basics
- 50:06MIME and ASCII problem
- 52:14HTML email challenges
- 54:00Testing and debugging tools
- 56:51Dark mode paradox
- 57:55Email as moving target
- 58:58Email resilience
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