There are a ton of free email providers out there, and for your general semi-anonymous eBay, internet porn or chat forums, they do an excellent job. More:Anonymous Email
Email providers are regularly sent court order requesting information. All you email, your address book, logs of when and where you connected from, any payment data including credit cards, are all handed over. (used to be my job - why do you think I'm writing this site!)
If it works for you:
- Always use SSL for web mail. I.e. check the URL, it should start with https://
- In your email program, check the "SSL" option
- Use the obscure port, often provided by your email server to get around your ISP blocking ports 25 (SMTP), 110 (POP) and 143 (IMAP)
An example from Outlook express
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