The article focuses on detection of smuggling and conducting an investigation in connection with car smuggling from Poland to the Kaliningrad District of the Russian Federation. The authors analyze a specific type of car smuggling incomparable to those typical of other Russian regions. The article also presents ways of evading customs fees while smuggling motor vehicles. The authors discuss organized criminal gangs involved in car smuggling in Poland, Lithuania, and the Kaliningrad District and present their crime patterns. At present, investigative and judicial practices indicate that car smuggling is of an organized, professional and, very often, international nature. (Published Abstract)