Canary Mail
One of the few mail clients that ships real encryption rather than just an AI compose box - PGP, HIPAA-oriented SecureSend and misdirected-recipient checks sit behind the same $100-a-year licence that covers every platform. The free tier is genuinely usable on two devices. Device caps rather than seats are the thing to watch, and there is no API or team administration.
Pros
- Native clients for Mac, Windows, iOS and Android under one per-user licence
- PGP plus SecureSend encryption aimed at HIPAA workflows
- Phishing, impersonation and misdirected-recipient detection built in
- AI copilot drafts replies, summarises threads and categorises mail
- Free tier on two devices and lifetime purchase options as an alternative to subscriptions
Cons
- Paid plans cap you at 5 devices, which is tight for a multi-device user
- Lifetime licence prices are advertised but not published
- No API, shared inbox or team administration
- Published entity is a Singapore company with no address given on the site