Objectives: To determine whether individuals with and without Chronic Ankle Instability (CAI) can improve their ankle movement discrimination sensitivity by repeated exposure to an ankle proprioceptive task requiring landing. Design: A repeated-measures study. Setting: University laboratory. Participants: 24 university students, 11 with CAI and 13 without CAI. Main outcome measures: Ankle proprioception was measured using the Ankle Inversion Discrimination Apparatus for Landing (AIDAL) over 3 occasions: AIDAL-1 and AIDAL-2 separated with a 10-min interval, and AIDAL-3 at 24 h post AIDAL-2. Results: Better Cumberland Ankle Instability Tool (CAIT) questionnaire scores were correlated with higher AIDAL scores (rho = 0.465, p = 0.022). Two-way ANOVA showed a significant CAI main effect for step landing ankle inversion proprioception, with CAI worse (F = 8.410, p = 0.008), but the Time main effect across the 3 AIDAL tests was not significant (F = 1.552, p = 0.223). Conclusions: The AIDAL assessment was sensitive in terms of discriminating between individuals with or without CAI. However, the step-down component of the AIDAL proprioceptive task was possibly too challenging. For CAI, physical therapy exercises should take into account the difficulty of the training task, so that a demonstrable learning effect can be achieved.