Abstract: Ship-To-Ship (STS) crude oil transfer at sea is an operation where crude oil is transferred between seagoing ships moored alongside each other. Due to the complex sea conditions and the poorer lightering facilities compared with the port operations, the risk of the operations is higher. Even though the frequency of incidents involving lager oil tankers has been reduced during recent decades, the consequences of such incidents can be very serious. In order to enhance regulation of STS operation and reduce risk of oil spill accidents, the study examined the existing regulation system and proposed an enhanced intelligent regulation system supported by modern Internet of Things technology. The framework of the intelligent regulation system was described in detail which included several intelligent monitoring means and a decision support system based on risk assessment.