I am new to Highrise. I trust 37 Signals, and I feel safe posting confidential information there. My question is this: when does highrise send email out? If I enter a contacts email in there but not as a user, are they going to be notified?

Thank you for your time,
Dan

No. Highrise doesn’t send out emails to people when you add them as a contact. Only when you invite them as a user.