A son of Viceroy Laukpya of Myaungmya, Shein actively participated in his father's rebellion against King Razadarit of Hanthawaddy, and fought in the subsequent Ava–Hanthawaddy War (1385–1391) on the Ava side.
Though he successfully defended Bassein in 1389, Shein decided to evacuate the port city when his father's provincial capital Myaungmya unexpectedly fell in 1390.
His caravan of elephants carrying loads of treasures soon found their path to Ava territory blocked by a Hanthawaddy battalion, and were forced to make a detour to Sandoway in Arakan.
[note 5] Their heavily fortified port city's defenses, which also included war boats manned by foreign mercenaries equipped with guns,[note 6] withstood repeated frontal charges by Hanthawaddy forces, inflicted heavy casualties on the enemy, and eventually forced them to retreat.
When Razadarit's forces unexpectedly captured his father's capital Myaungmya in early 1390, Shein and his deputies quickly decided to evacuate Bassein for Prome (Pyay), Ava's southernmost garrison.
Upon hearing the news about the evacuation two days after Myaungmya's fall, Razadarit dispatched a battalion to catch Shein.
They soon found their path to Prome blocked by the Hanthawaddy battalion, and had to make a detour to Sandoway (Thandwe), 300 km (190 mi) northwest of Bassein, in Arakan.