The article is an attempt to find answers to the fundamental questions of which Roman province the individual islands belonged to and from when. The literature on the subject frequently presents the opinion that some of the Aegean Islands were incorporated into the province of Asia at the moment of its creation. The status of the other islands was, in turn, regulated by Augustus. After a meticulous analysis of sources, the author shows that such an image is oversimplified. The administrative affiliation of the individual islands changed depending on the political circumstances and the good or bad will of the Roman generals operating in the East. The efforts of the islanders themselves were also not without significance. The locations of the individual Aegean Islands were very different, and some of them formally became part of the Roman Empire only during the Flavian rule.