Winkler continues to perform these espionage simulations, as well as assist organizations in developing cost-effective security programs. Winkler won the Hall of Fame award from the Information Systems Security Association, as well as several other prestigious industry awards. CSO Magazine named Wimkler a CSO Compass Award winner as The Awareness Crusader. He was named 2021 Top Cybersecurity Leader by Security Magazine, and 2022 Cybersecurity Champion of the Year by the Cybersecurity Association of Maryland.