During the COVID-19 pandemic, social isolation had a devastating effect on well-being. Veterans were among the most vulnerable given their high rates of military trauma-related conditions. Research supports that dogs can provide veterans with a sense of purpose, social support, and stress management. Digital storytelling provided a unique perspective with focus on a recognized hero, the veteran's dog, and an opportunity for engagement with other veterans during COVID-19. The purpose of the study was to assess the feasibility of this digital storytelling intervention based on Story Theory framework and tailored to encompass components of cross-generational collaboration in combination with individual and group virtual sessions as a mechanism to promote social engagement. The research was conducted using a descriptive exploratory design. Veterans (N = 8) were paired with a trained student and grouped in sets of four. There were eight guided 1-hour weekly virtual sessions to create their digital story. Demographic and pre-post intervention survey data were also collected. Based on eight established criteria, this article systematically evaluates the feasibility of the digital storytelling intervention for veterans. The findings suggest practical considerations to ensure viability of digital storytelling as a therapeutic intervention for veterans and other populations at-risk for suboptimal well-being.