There is a global danger that hides in the shadows and is changing the way continuing care operators care for residents. Today, to provide that same historical level of resident care, a group of techno-soldiers are not just a nice-to-have, but are a must, to protect our critical Information Technology (IT) infrastructure. There is little doubt that technology has enabled us to provide better care. Electronic medical records, human resources information systems, and voice over Internet communications systems have created great efficiencies in operations. However, global cybercriminals lurk in the same technologies that support us. Continuously attempting to rob our private information and hold us ransom, or play havoc with our IT systems impeding our provision of care. How can a continuing care operator, an already funding-challenged industry balance the costs of protecting their IT infrastructure against this growing massive threat? Compounding the issue, rising insurance expectations for continuing care operators to continuously enhance their IT safety controls against evolving cyberterrorism. This is the story of the Good Samaritan Society/Canada (Good Samaritan) digital transformation journey. Our digital roadmap sets Good Samaritan up to rise above the ongoing barrage of cyberattacks and loss of insurance. This is a digital divide story of David vs. Goliath.