What SSL/TLS protects
An email makes at least two trips, and SSL/TLS can protect each one separately:
- Your app to your provider. When Outlook, Apple Mail or your website sends mail through SMTP, or reads it through IMAP or POP3. This is the setting you choose, and the one you should always have on: without it your password crosses the network in plain text.
- Your provider to the recipient's provider. Mail servers try to upgrade each delivery to TLS with STARTTLS. You don't control this hop, but large providers like Gmail and Outlook use TLS whenever the other side supports it.
SSL/TLS does not encrypt the message where it is stored. Your provider and the recipient's provider can read it. If you need that, use S/MIME or PGP on top.
SSL, TLS and STARTTLS: what the settings mean
- SSL/TLS (sometimes just "SSL", or "implicit TLS"): the connection is encrypted from the first byte. Used on port 465 for SMTP, 993 for IMAP and 995 for POP3.
- STARTTLS: the connection starts unencrypted on the normal port, then the client asks the server to switch to TLS before logging in. Used on port 587 for SMTP.
- None: no encryption. Only acceptable inside a private network. Most providers refuse to let you log in this way.
Both SSL/TLS and STARTTLS end up with the same TLS encryption. The most common mistake is mixing them up: SSL/TLS on port 587, or STARTTLS on port 465. The connection then hangs or fails before login.