Most people tended to use their own ISP's mail servers back then. Hotmail, Yahoo, and AOL were the only third-party email services around, before the likes of Gmail took off. It would be trivial to go look at mail server logs to see if X login was connecting every X minutes.
Encryption was seldom used there for POP3/IMAP/SMTP because hey you're on the same ISP network and not crossing the Internet. Further it was pretty easy to hop on a terminal server like a Portmaster and do a debug/packet dump of individual dialup connections if somebody really wanted to see what somebody was doing.
Encryption was seldom used there for POP3/IMAP/SMTP because hey you're on the same ISP network and not crossing the Internet. Further it was pretty easy to hop on a terminal server like a Portmaster and do a debug/packet dump of individual dialup connections if somebody really wanted to see what somebody was doing.