The development of rehabilitation engineering technologies such as the design of smart prosthetics necessitates a deep understanding of brain mechanisms engaged in ecological situations when human interact with new tools and/or environments. Thus, we aimed to investigate potential hemodynamic signatures reflecting the level of cognitive-motor performance and/or the internal or mental states of individuals when learning a novel tool with unknown properties. These markers were derived from functional Near Infrared Spectroscopy (fNIR) signals. Our results indicate an increased level of oxy-hemoglobin in prefrontal sensors associated with enhanced kinematics during early compared with late learning. This is consistent with previous neuroimaging studies that revealed a higher contribution of prefrontal areas during early compare to late adaptation learning. These non-invasive functional hemodynamic markers may play a role in bioengineering applications such as smart neuroprosthesis and brain monitoring where adaptive behavior is important.