Bioinspired fibrillar adhesives have been proposed for novel gripping systems with enhanced scalability and resource efficiency. Here, we propose an in-situ optical monitoring system of the contact signatures, coupled with image processing and machine learning. Visual features were extracted from the contact signature images recorded at maximum compressive preload and after lifting a glass object. The algorithm was trained to cope with several degrees of misalignment and with unbalanced weight distributions by off-center gripping. The system allowed an assessment of the picking process for objects of various mass (200, 300, and 400 g). Several classifiers showed a high accuracy of about 90 % for successful prediction of attachment, depending on the mass of the object. The results promise improved reliability of handling objects, even in difficult situations.