In this article we explore how digital play as conducted through various social media and online meeting platforms facilitated resiliency and confidence building in children during the COVID-19 pandemic. Using day-in-the-life methodology and narrative inquiry, we disseminate and examine observations collected on children aged 2-10 during lockdown in a Newfoundland neighbourhood. Children utilized platforms such as TikTok, YouTube, and Zoom to embrace their agentic digital play in ways that repurposed the platforms to fulfil life milestones and social needs otherwise impacted and disrupted by pandemic restrictions. Through a series of vignettes and interviews, our research not only examines how such digital play benefits children and their healthy development, but how parents reacted to and assisted with their children's agentic digital platform manipulation and how this provided positive benefits and enriching experiences to the entire family. We additionally explore the conflicts and tensions both children and parents encountered in securely implementing free play via digital platforms, including fears of excess screen-time, digital dependency, and online threats, all of which risk limiting children's ability to independently explore their creativity and identities through digital play if not handled sensitively. Despite the hurdles to implementing digital play, this study exposes why it is essential for families to navigate this online terrain; this study ultimately poses that digital play and online platforms not only were beneficial to maintaining and building family resilience during the pandemic but will be vital assets in sustaining resiliency and positive mindsets moving forward with pandemic recovery.