Social engineering attacks, such as phishing attacks, remain one of the main reasons why so many cyberattacks are happening every day. Although social engineering is not new, and several countermeasures have been proposed time-to-time, social engineering has evolved with technology, making old countermeasures obsolete. The recent technologies, such as Large Language Model, Deep Fake, and widespread use of live video conferencing, etc., have made social engineering very sophisticated. The available countermeasures are becoming ineffective to deal with such sophisticated forms of social engineering. Phishing remains one of the main forms of social engineering. The proposed project aims to (1) study the effect of recent technologies on sophisticated social engineering attacks, and (2) design a technology- enabled chatbot tool to address sophisticated phishing. The tool can act as a companion and assist people by providing a second opinion on whether something looks like a phishing attack or not. This four-years-long research will pave ways for future research to develop a full- fledged chatbot for dealing with phishing effectively.