Accurate quantification of soft tissue properties, specifically the stress relaxation behavior of viscoelastic tissues such as plantar tissue, requires precise testing under physiologically relevant loading. However, limitations of testing equipment often result in target strain errors that can contribute to large stress errors and confound comparative results to an unknown extent. Previous investigations have modeled this artifact, but they have been unable to obtain empirical data to validate their models. Moreover, there are no studies that address this issue for plantar tissue. The purpose of this research was to directly measure the difference in peak force for a series of small target strain errors within the range of our typical stress relaxation experiments for the subcutaneous plantar soft tissue. Five plantar tissue specimens were tested to seven incremental target strain error levels of −0.9%, −0.6%, −0.3%, 0.0%, 0.3%, 0.6%, and 0.9%, so as to undershoot and overshoot the target displacement in 0.3% increments. The imposed strain errors were accurately attained using a special compensation feature of our materials testing software that can drive the actuator to within 0% of the target level for cyclic tests. Since stress relaxation tests are not cyclic, we emulated the ramp portion of our stress relaxation tests with 5 Hz triangle waves. The average total stress variation for all specimens was , with the highest and lowest stresses corresponding to the largest and smallest strain errors of 0.9% and −0.9%, respectively. A strain overshoot of 0.3%, the target strain error observed in our typical stress relaxation experiments, corresponded to an average stress overshoot of . Plantar tissue in compression is sensitive to small target strain errors that can result in stress errors that are several fold larger. The extent to which the overshoot may affect the peak stress will likely differ in magnitude for other soft tissues and loading modes.