In diffuse optical tomography (DOT) and spectroscopy (DOS) using handheld probes, tissue curvature can cause bad fiber-to-tissue contact. Understanding and minimizing image artifacts caused by these coupling errors would significantly improve DOT and DOS image quality. In this work, we utilized Monte Carlo simulations and experiments with gelatin-Intralipid phantoms to systematically study the influence of source or detector (optode) coupling errors. Optode coupling errors can increase the amplitude and decrease the phase of the measured diffuse reflectance, creating artifacts in the reconstructed absorption maps, such as hot spots on the edges. We propose an outlier removal algorithm that can correct these image artifacts, and we demonstrate its performance using simulations, phantom experiments, and breast patient data acquired with bad probe contact due to a dense or small breast. Further, we designed and implemented a new resistance-type thin-film force sensor array that provides real-time optode coupling feedback and guides the outlier removal to minimize optode coupling errors. Our approaches and study results have significant implications for reducing image artifacts arising from handheld probes, which are commonly used with mobile and wearable DOT and DOS devices.