Cpl. Osellame chose the Military Police branch after basic training and has held positions in Barrie, Brandon, Toronto and Afghanistan.

As part of the Royal Canadian Regiment, he was assigned to be part of a Police Observation and Monitoring Liaison Team, living in a compound about 100 kilometres outside Kandahar. He spent a total of seven months in Afghanistan, facing firefights, improvised explosive devices and the constant threat of insurgent attacks on the road outside the compound.