Highly scaled direct gravure is a promising printing technique for printed electronics due to its large throughput, high resolution, and simplicity. Gravure can print features in the single micron range at printing speeds of 1 m/s by using an optimized cell geometry and optimized printing conditions. The filling of the cells on the gravure cylinder is a critical process, since the amount of ink in the cells strongly impacts printed feature size and quality. Therefore, an understanding of cell filling is crucial to make highly scaled gravure printed electronics viable. In this work we report a novel experimental setup to investigate the filling process in real time, t coupled with numerical simulations to gain insight into the experimental observations. By varying viscosity and filling speed, we ensure that the dimensionless capillary number is a good indicator of filling regime in real gravure printing. In addition, we also examine the effect of cell size on filling as this is important for increasing printing resolution. In the light of experimental and simulation results, we are able to rationalize the dominant failure in the filling process, 1.e., air entrapment which is caused by contact line pinning and interface deformation over the cell opening.