During her time on the Balkan Front, she would go on to work as a military engineer, a guard for the Scottish Women's Hospitals, and become a prisoner of war under the Bulgarian Army following the invasion of Belgrade on October 8, 1915.

According to an article from January 8, 1916 in the Manitoba Free Press, Winnipeg, Whitehead lived an "outdoor life" for "a couple of years […] in the Laurentian Mountains at Val Morina".

[2] The Toronto Daily Star also reported that "Miss Whitehead" was "extremely fond of outdoor life, wore semi-male garb on her tramps through the woods, and could handle a canoe or shoot better than most men".

Travelling to London, England, Whitehead volunteered, alongside "a batch of young ladies from Canada", to work "long hours over the card index and the typewriter in order to", as the Yorkshire Evening Post reported on June 3, 1915, "keep the people of" her "own country informed of the condition of the wounded among the Canadian contingent".

[6] Conflict zones were deemed far too dangerous a place for the "weaker sex" to be, with some even considering it an abomination that the female life-giver should enter the battlefield, where she stood to witness brutal and unrelenting loss of life.

[9] According to contemporary newspaper sources, Whitehead was "acting as a lieutenant in the Veterinary Corps of the Serbian Army, having given up hospital work" so "she might get closer to the firing line" when Serbia's occupation began.

Finding themselves frequently targeted by thieves in the form of desperate locals, prisoners of war and enemies alike, the Scottish Women's Hospitals recruited Whitehead as a "guard" in the hopes that she would help to deter the near-daily pillaging of resources and supplies.

[12] At the time of being made a prisoner of war, The Globe cites Whitehead "was captured by the Bulgarians while serving with a British veterinary corps in Serbia" – a division she had joined "owing to her knowledge of horses".