Work-the-Walk (WTW) is a teaching and learning approach that uses a type of blended learning model, which is flipped classroom, as its basis. The philosophy lies in the absence of lectures during face-to-face sessions, and the approach relies heavily on Socratic Dialogues and classroom activities to enhance the understanding of lessons of the day. With the outbreak of COVID-19, education at all levels must continue. Often, the challenge is on ensuring that students, who must attend remote learning are able to own their learning process, and that they are also able to relate to their environment. The objective of this paper is to discuss how to humanize students’ learning experience and environment by observing how digitization of WTW promotes the sense of ownership through active learning. This paper addresses two questions, including the implementation of WTW during remote learning (Digital WTW or D-WTW), and students’ understanding on the lessons of the day when D-WTW is used. The methodology adopted for this research was qualitative by means of observations of students’ participation during online synchronous activities. Two important findings are evident when D-WTW is used. The first one is that students become more confident in their articulation of ideas, and second, they become more engaged during the remote learning sessions. These could be contributed to the concept of humanizing online activities and the learning environment that allow them to explore and tap into their potential, and ultimately, these strengthen their learning experience.