Background and Purpose: Older adults with lower balance confidence demonstrate a reduced willingness to experience instability as the task of walking becomes more challenging (i.e., walking with a faster speed). However, the specific reason why is not known. The purpose of this study was to investigate the extent to which capacity of increasing walking speeds relates to the attentional requirements (i.e., automaticity) of walking. Methods: Sixteen young (31 ± 5.85 years) and 15 older participants (69 ± 3.04 years) began walking on a treadmill at 0.4 m/s, and speed was increased by 0.2 m/s until the participant either chose to stop or reached a speed of 2.0 m/s. Sixty steps were collected at steady-state speed for each walking trial. Kinematic data were collected, and the margin of stability in the anterior direction (MOSAP) at heelstrike was quantified for each step. The timed up and go (TUG) and TUG dual (TUGdual) task were performed, from which an automaticity index (TUG/TUGdual × 100) was calculated. Older individuals were grouped based on whether they did or did not complete all walking speeds (i.e., completers [n = 9] or noncompleters [n = 6]). The fastest walking speed attempted (FSA), automaticity index, and MOSAP were compared, and correlations were assessed between the FSA/MOSAP and the automaticity index. Results: A significant difference was identified in an average MOSAP at heelstrike between older completer and noncompleter groups (p < 0.001). Further, older adults with lower automaticity index choose to stop walking at lower speeds (p = 0.001). The FSA was positively correlated with the automaticity index (ρ = 0.81, p < 0.001). Finally, the average MOSAP at FSA and the automaticity index were also negatively correlated (r = -0.85, p < 0.001). Conclusion: Older adults with lower automaticity of walking choose to stop walking at speeds before they completed all walking speeds, which may relate with increased attentional demands required to maintain dynamic stability at higher walking speeds. Given that these were otherwise healthy adults, the combination of FSA and an automaticity of walking may help to identify individuals who should be considered for an assessment to identify walking problems.