End-to-End Options: PGP and S/MIME Explained

Ricardo Signes, Chief Engineer at Fastmail, explains why Gmail's email experience has become increasingly fragmented, and what it would take to actually fix the decades-old IMAP protocol that powers most of the internet. We dive deep into JMAP (the modern replacement Gmail won't adopt), privacy-by-design vs. encryption theater, and the hidden trade-offs between convenience and security that no one talks about. If you've noticed your email client feeling broken, this interview reveals why.

📱 RESOURCES IN VIDEO:

• Fastmail: https://fastmail.com

• Fastmail Values Statement: https://fastmail.com/about/values

• Cyrus IMAP/JMAP Server (open source): https://www.cyrusimap.org/

• JMAP Standard (RFC 8620): https://tools.ietf.org/html/rfc8620

• Web Push Standard (RFC 8030): https://tools.ietf.org/html/rfc8030

• Signal (for encrypted messaging): https://signal.org

• Fastmail Data Transparency Report: https://fastmail.com/about/transparency

Timestamps:

0:00:00 INTRO

00:01:36 WHAT DRAWS YOU TO FASTMAIL?

00:03:29 FASTMAIL VALUES & PHILOSOPHY

00:08:49 FASTMAIL TARGET USER

00:12:43 LACK OF NATIVE E2EE

00:16:16 WILL EMAIL EVER BE PRIVATE?

00:18:23 FASTMAIL E2EE OPTIONS

00:23:43 FASTMAIL CLIENT OPTIONS

00:26:18 FASTMAIL INTEGRATIONS

00:29:49 BEING GOOD INTERNET CITIZENS

00:33:13 BAD INTERNET CITIZENS

00:38:26 JMAP & OTHER EMAIL PROTOCOLS

00:48:15 REAL-WORLD BENEFITS OF JMAP

00:53:07 ISSUES WITH GMAIL ON IOS

00:56:06 LACK OF E2EE FOR EMAIL WITH ADP

00:57:29 DOES JMAP MAKE E2EE EASIER?

01:00:43 FASTMAIL + OPEN SOURCE

01:10:48 PROTECTIONS AGAINST BAD ACTORS

01:14:46 PHONE NUMBER REQUIREMENTS

01:22:55 AUSTRALIAN JURISDICTION

01:25:55 THE FASTMAIL TEAM

01:28:45 PRODUCTIVITY-FOCUSED EMAIL CLIENTS

01:34:27 FASTMAIL + IMAP

01:35:49 WHY THE NAME "FASTMAIL"?

01:38:27 IS JMAP WHY FASTMAIL IS SO FAST?

01:42:03 FASTMAIL'S IDEAL AVATAR + FUTURE PLANS

01:46:25 HOW TO FOLLOW RICARDO + FASTMAIL

01:48:03 OUTRO

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