This empirical chapter investigates 10 UK-based NPOs to understand the preconditions that shape their digital transformation (DT) journeys. Through cross-case analysis, it identifies organizational, technological, ecosystemic, and behavioral factors that either enable or constrain digital development. The study highlights significant heterogeneity across NPOs, revealing a spectrum of readiness levels and transformation logics. The chapter also offers methodological transparency by detailing data collection, coding, and analytical procedures supplemental to the empirical findings.