Following the emergence of the COVID-19 pandemic, the entire healthcare community moved to adopt rapid digital healthcare solutions to avoid and reduce the adverse effects of pandemics. Although launching any digital healthcare solution or tool contributes to resolving or reducing the impact of the dilemma, still the agile development challenges behind this are not well structured or categorized yet. The current agile development of digital healthcare solutions is surrounded by difficulties that must be well-identified and synthesized to overcome and to specify and develop more robust solutions that are digitally ready for transformation. This research proposes a review-driven and expert-validated comprehensive classification for challenges that emerge under the agile development of digital healthcare applications, as the first deliverable in this research. The review covers the years 2020–2024. The classification contributes to deriving another deliverable in this research, that is a digital readiness framework for the agile development of digital healthcare solutions. The digital readiness framework contributes to act as a foundation for sustainable digital transformation and improving healthcare outcomes.