Why don't you use email encryption?
jodrellblank: Encryption is all mixed up with PKI and certificates and that whole bundle of (overly)complex stuff that I really don't want to have to bother with any more than I have to.I think I have GPG running somewhere, but know only one person who used it. I like that they pushed me to use it, but haven't needed to email them since.Whatever it was would have to work on all the ways I read my main email (iPhone, Browser, Outlook), and not involve typing a decryption password for every email or even every time I check for mail.