Bruce Cockburn's brother, Capt. John Cockburn, spent many years as an ER doctor specializing in anesthesiology before joining the army later in life. In late 2009 Cockburn made a trip to Kandahar, Afghanistan to visit his brother and to play a concert for the Canadian soldiers. Several of the songs on his 31st album, Small Source of Comfort, were influenced by this experience and this track was inspired by the death of two Canadian soldiers who had just been killed. Cockburn found himself standing on the tarmac as during a moving ceremony, the two coffins were loaded onto a plane to be sent home. He told Christianity Today that he was touched by "the incredible dignity of the ceremony and the empathy of the troops, knowing it could have been them. There was an incredible depth of feeling all around - a lot of tears and a sense of seriousness."
The first half of the song is written from Cockburn's perspective. The second half of the song is written from the perspective of the fallen soldier.
"Pretty In Pink" by Psychedelic Furs was released in 1981. Five years later, it inspired a movie of the same name starring Molly Ringwald, Andrew McCarthy and Jon Cryer. The song was remixed for the re-release to have more Pop appeal.