A system and method is described that sends multiple simulated phishing emails, text messages, and/or phone calls (e.g., via VoIP) varying the quantity, frequency, type, sophistication, and combination using machine learning algorithms or other forms of artificial intelligence. In some implementations, some or all messages (email, text messages, VoIP calls) in a campaign after the first simulated phishing email, text message, or call may be used to direct the user to open the first simulated phishing email or text message, or to open the latest simulated phishing email or text message. In some implementations, simulated phishing emails, text messages, or phone calls of a campaign may be intended to lure the user to perform a different requested action, such as selecting a hyperlink in an email or text message, or returning a voice call.