He was awarded the United States Bronze Star Medal with "V" device for his actions in combat and was Mentioned in Despatches by the Canadian Forces.

Ragsdale began his military career with the 2nd Commando of the Canadian Airborne Regiment before transitioning to the 3rd Battalion PPCLI.

[1] In 1991, after his initial three year service contract, he chose to be released from the regular force and joined the Canadian Rangers Patrol Group.

He rejoined the regular force in 1996 and was posted to the newly formed 3rd Battalion Princess Patricia's Canadian Light Infantry.

[7] He worked many years as a designated defensive marksman in a counter-sniper role for various private military companies throughout Afghanistan and the Maghreb region of North Africa.