The European Commission’s proposed regulation on cloud computing and AI procurement marks a turning point for how regulated entities—and, by extension, their private-sector partners—approach digital transformation. At the same time, new research reveals a striking paradox: while 98% of enterprises have at least one AI initiative underway, only 3% consider themselves fully ready to scale it. For boards and C-suites navigating cloud migration and emerging technology investment, the gap between regulatory ambition and operational readiness has never been more consequential.