Since the covid pandemic, some higher education institutions have promoted a flexible evaluation approach for students who face a variety of problems. Instructors willing to implement such flexibilizations face an important challenge: making themselves aware of students going through hard times. This evidence-based practice paper presents an overview and a preliminary evaluation of the well-being teaching assistant (WTA), an approach to facilitating communication, suggesting and documenting flexibilizations, and providing support for students going through difficult times in high-enrolment courses. WTAs are regular members of the teaching assistant staff, but they use an early warning system to identify potential students at risk of failure, initiate communication using supportive language, and take action by suggesting flexibilization or providing academic support for students facing challenges. WTAs have been incorporated into 27 courses at a large school of engineering in Latin America, during 2022, and have been positively evaluated by students. One of the main current challenges of the approach is scalability.