William Woodruff

William Woodruff, founder of Yossarian.net, joins the discussion to dismantle the myths surrounding encrypted email, especially PGP. He reveals a significant bug in an OpenPGP library, arguing that email was never designed for encryption. The conversation dives into operational security, criticizing outmoded methods like PGP and S/MIME. They explore the risks of metadata leaks and the limitations of federated systems, advocating for modern secure messaging alternatives like Signal over traditional email. Woodruff emphasizes the need for better understanding of digital threat models.