This paper elaborates on a curious episode in the career of Iphicrates-famous Athenian strategos and mercenary commander in the first half of the 4th century B.C. According to Theopompus [FGrH 115 F 161], Iphicrates was somehow involved in a settlement of the Thracian town of Drys. His presence there is also corroborated by a testimony of Demosthenes [XXIII 131-132], but the rhetor does not precise what Iphicrates' exactly did there. Both sources mentioned above, as well as several others, will be re-examined in this article, eventually leading to a proposal of a different interpretation of Theopompus account and the entire historical episode. Namely, the article suggests that the relevant fragment of Hellenica should be understood as a reference to the reconstruction program of Drys conducted or at least initiated by Iphicrates. The town had presumably suffered some downfall before, which could have been a result of an engagement between Spartans and Athenians, as described by Polyaenus. This event is often placed by modern scholars around the year 375 B.C., although this article opts for an earlier period, one contemporary with the Corinthian War. This way, Iphicrates could have been involved in the re-settlement of the town in the second half of 380s, after he has married a princess of Seuthes’ family. Furthermore, it is suggested that the title of Anaxandrides' fragmentarily preserved comedy "Protesilaos" was considered by the author to be a reference to Iphicrates and his activities in Thrace.