Yes, should be. Even non personal information should probably be encrypted. Doesn't take any more time on your part.. and you would be amazed the kind of identifiers even seemingly 'non personal information' might potentially reveal. Your scenario is an acceptable method given both your safe-mail password is complex, your PGP password is extremely complex. There's no point in even starting an email with "Hi.. sorry I've been busy with work/family (whatever). Here's my address and shipping information -----BEGIN PGP MESSAGE----- etc" It should be more like: -----BEGIN PGP MESSAGE-----..etc and nothing else. Encrypt your pleasantries.. you'll be better served.