A strong Canadian Armed Forces (CAF) is beneficial to all Canadians. The CAF provide necessary security for the nation, North America, and internationally. The process of building a suitable and sustainable force to meet their mandate, as set by the Government of Canada, is time-intensive and expensive. This situation underscores the necessity of retaining well-trained personnel to allow the CAF to accomplish their missions, while ensuring the next generation is adequately prepared to carry on and adapt to new government priorities. Currently, maintaining an adequate number of military members is a struggle and research is required to better understand why this is the case. Rittel and Webber’s ‘Wicked Problem’ theory, in which social policy issues are unsolvable and instead need to be managed indefinitely, provides valuable insight. To demonstrate that the retention problem within the CAF is a wicked problem, a combination of primary and secondary data analysis on the CAF, and a comparative case study were completed. As a wicked problem, the CAF need to recognize that retention is an issue that can only be managed, not solved. While clear similarities exist between the CAF and NZDF, especially around military families, the Canadian provincial system, compared to the New Zealand unitary system, creates additional complications, none of which the CAF can fix. Future research is required to understand the retention issue in Canada, specifically in terms of the potential relationship between military equipment procurement and retention, as was recognized within the NZDF.