The last mention of his name in the sources is from 1366. He appears in the charters as κῦρ or δοῦλος of the Serbian Empress Jelena (Helene) and of the Serbian Despot Ioan Uglješa (Ioannes Unklesis). He repeatedly judged in a court as καθολικὸς κριτής between 1365 – 1366 in Serres. He held the office of ἐπὶ τοῦ στρατοῦ in Serres (1365 – 1366) and ἐπὶ τοῦ κάστρου in Serres (eventually from 1350 to 1366). He erected the tower at Serres in 1350 at the behest of the Serbian Emperor Stefan Uroš IV Dušan (Πύργος Στεφάνου βασιλέως ὅν ἔκτισεν Ὁρέστης Αὐγούστου Δʹ Ινδικτιωνος Γ ΩΝΗ). He participated in the decision over a plot of land in the village Zetinon (Zintzu) and a Church of Saint George (τῶν εὐγενεστάτων καὶ καθολικῶν κριτῶν, τοῦ τε κῦρ Ὀρέστου τοῦ ἐπὶ τοῦ στρατοῦ). He corroborated the document issued by Sabas, the Metropolitan of Serres, by his own signature in August 1365 (ὁ δοῦλος τῆς κραταιᾶς καὶ ἁγίας ἠμῶν κυρίας καὶ δεσποίνης καθολικὸς κριτής, Ὀρέστης † Ὁ ἘΠΙ ΤΟΥ ΣΤΡΑΤΟΥ). He attended the trial between Hilandar Monastery and Georgios Isaris (τοὺς καθολικοὺς κριτάς, τὸν ἐπὶ τοῦ κάστρου κῦριν Ὀρέστην). He together with other members of the court ruled in favor of the Hilandar Monastery and signed the charter issued on this occasion (ὁ δοῦλος τοῦ ἁγίου μου αὐθέντου τοῦ πανευτυχεστάτου δεσπότου καθολικὸς κριτής, Ὀρέστης † ὁ ἐπὶ τοῦ στρατοῦ).