Evolution has evolved fascinating resource-efficient and sustainable materials architectures to ensure survival. Inspired by nature, micropatterning of polymeric surfaces has become a powerful paradigm: celebrated examples range, e.g., from controlled wetting and anti-icing to coloration and switchable adhesion. Fundamental adhesion studies have not only demonstrated the benefit of microfibrillar architectures but have also inspired innovative pick-and-place systems or delicate adhesives for skin and body organs. But several problems remain: how do we release micro-objects with negligible mass? And how can we ensure reliability of gripping, also in demanding conditions such as in space? We have proposed a machine-learning based optical monitoring system that images the individual fibrillar contacts in operando. Several classifiers predict successful handling with a high accuracy, indicating, e.g., incomplete or off-center gripping. The improved reliability of this technology will impact everyday life as eco-friendly solutions will be increasingly essential for our own survival.