Gwynn passed through Sire in late October 1908 en route to his assignment to delineate the border between Kenya and Ethiopia.

He describes the settlement's location at the time as "halfway up the scarp" on the southern side of the Awash River, and Sire itself as "a small Abyssinian village and customs post".

He was struck by its "curious little church consisting of a stone-built cube, surmounted by a sharp steeple-like roof, also of stone", which he speculated was originally a Muslim shrine "similar to that at Sheikh Hussein and others in the Arussi country.

Sire was one of the twelve Woredas or districts within the now defunct Chilalo County (Cilaaloo Awrajja) during the times of Emperor Haylasillasie and Provisional Military Administration Governments of Ethiopia.

After fierce battles with the local people the Shewan invading army finally conquered the place and established a garrison.