Anderson, went overseas with the first Canadian contingent. The 101st contributed the entire 9th Battalion, but the 9th was broken up to reinforce the 1st Brigade; thus, they almost all ended up in Ontario units. He was taken prisoner at 2nd Ypres on May 9, 1915, but he escaped in October 25, 1915 using his knowledge of languages to bluff his way back to England after his escape. It is believed that he was the only Canadian officer to successfully escape during the war.
In a humorous letter to the Commandant of the POW Camp he has escaped from he wrote “It was on April 24, 1915 that I was taken Prisoner at Ypres after every Man that was with me was Killed. I was blown up twice and when I woke up I was a Prisoner. I arrived at your Hotel on 28th of April and it is no doubt, one of the best, if not the best Prison Camp in Germany… No one ever had got out of a prison camp, but there is always some way of getting out. I had been a big game hunter all my life. I can go get the big bull moose, elk, deer, grizzly bear. That being the case, yours or any one else’s sentries are worth little or nothing as far as I am concerned…”