Issa is a Greek colony, presumably founded at the beginning of the 4th century B.C. on the island of Vis, located in the central Dalmatian archipellago. One of the first mentions of the colony is already in the middle of the 4th century B.C., and the most notable authors are: Pseudo – Skylax, Theopompus, Pseudo – Scymnus, Diodorus Siculus and Strabo. In the 17th century while studying the work “Bibliotheca” by Diodorus, a debate was started about the correctness of the transcription. The work mentions the foundation of Dionysius’ city Lissos, whose name is considered to have been transcribed incorrectly, and Issa should have been written instead. According to this interpretation of the work, it should be considered that Issa was founded by Dionysius the Elder in 397 B.C. as his stronghold on the southern Adriatic. However, the problem occures when we compare our interpretations of ancient written sources and showings by the material found via archaeological research. The findings of coins, ceramics and other objects in the area of ancient Issa, are dated earliest to the middle of the 4th century B.C. This fifty year gap that is shown between the written source and the archaeological findings leaves an open debate on the question; Who actually founded Issa, when and why?