To support the vision of 21st century learning, Institute of Technical Education (ITE) had established a digital education culture throughout ITE students’ learning journey that enables all lecturers and students to stay connected on and off campus; collaborating with peers, creating knowledge, managing learning and monitoring progress. ITE has been developing substantial frameworks over the years to adopt technology-enhanced learning to engage, motivate, and inspired learners of all ages. In 2000 to 2004 under ITE Breakthrough strategic plan to create a world-class technical education institution for a knowledge-based economy, our curriculum was redesigned to create an IT-based teaching and learning environment for our students. Our first learning management system, eTutor, was implemented in 2002 to focus on the pillars of connectivity and accessibility. We had built a community of connected on-line learning campuses that allowed our students to access course material anywhere, anytime. Lecturers were trained to develop interactive courseware for self-directed learning. In 2005 to 2009 under ITE Advantage strategic plan to propel ITE into a global leader in technical education, our education became a key pillar to stay competitive in Singapore workforce and economy. ITE had developed the taxonomic role-play pedagogic model, iDe’Lite, for teaching and learning of Service Skills using video-based technology. Lecturers used various video editing, screen capture and screen recorder software to develop self-taught video content to inculcate students’ independent learning. Finally, in 2015 to 2019, the new ITE strategic plan - ITE Trailblazer had aspired to blaze new trails in teaching and learning, through use of ICT-enabled and teaching methods tailored to different disciplines. New learning management system, MyConnexion, is implemented. It provides a greater flexibility to engage both lecturers and students in teaching and learning with a more user friendly interfaces that encompasses various Web 2.0 collaborative tools. ITE has started BYOD (Bring Your Own Device) program in some of the courses from 2014 to 2015. The transition to mobile devices and digital curriculum redefine our educational approach through greater incorporation of info-comm technology, reinvent our learning spaces, and adopt discipline-specific teaching methods. Every ITE student will have more opportunities for authentic, flexible and self-directed learning, both in and out of ITE. This will prepare them to be active, skilled, creative, and ethical contributors to the global economy.