Phishing enhancement and phishing detection enhancement technologies. The technologies can include determinations of an effectiveness rate of one or more phishing threat actors. The technologies can also include selection of effective URLs from at least one effective phishing threat actor. The technologies can also include generation or adjustment of a phishing system using a machine learning process to identify patterns in the selected effective URLs that enable the selected effective URLs to avoid detection by the phishing detection system. The technologies can also include generation of synthetic phishing URLs using the phishing system and the identified patterns. The technologies can also include adjustments or training of the phishing system or the phishing detection system according to the synthetic phishing URLs to enhance the systems.