This paper describes a phenomenon that can advect multi-year ice features (floes, ice islands, and icebergs) from the permanent polar pack into the Chukchi Sea. Efforts to understand this phenomenon, which has been termed the "Multi-Year Gateway", were prompted by the discovery of a small ice island offshore of Pt. Belcher in the Alaskan Chukchi Sea in 2012. A sequence of four events was identified that can channel multi-year ice features from the Beaufort Sea into the Chukchi. Satellite images and ice charts from the past 21 years were used to study the frequencies of occurrence of the underlying events and the likelihood that a multi-year ice incursion would result in the Chukchi Sea. The inter-annual variability and long-term trends in the development of the Multi-Year Gateway are discussed.