In recent years, technology has played a vital role in enhancing the management of risk and reliability in engineering assets, presenting both new opportunities and unforeseen challenges. The strategic focus the modern-day managers has been on seeking transformative technological and business solutions to ensure the safe and cost-effective operation of engineering assets. These transformative technologies such as industrial Internet of Things, AI, Machine Learning, and 5G communication, offer highly effective maintenance solutions, empowering engineering managers to make informed decisions while minimizing costs. As a result, asset managers have embraced digital technologies across their assets, aiming for operational excellence. However, the journey of digital transformation must address various challenges, such as technological, business, and governance-related issues etc., to ensure the safe, reliable and sustainable operation of engineering assets. The presentation underscores the significance of digital and enabling technologies, examines associated issues and challenges, and explores future trends. It highlights the potential of enabling technologies for estimation of the remaining useful life of engineering assets and implementing maintenance strategies considering contextual information.