Abstract: Although pens and paper are pervasive in the analog world, their digital counterparts, styli and tablets, have yet to achieve the same adoption and frequency of use. To date, little research has identified why inking experiences differ so greatly between analog and digital media or quantified the varied experiences that exist with stylus-enabled tablets. By observing quantitative and behavioural data in addition to querying preferential opinions, the experimentation reaffirmed the significance of accuracy, latency, and unintended touch, whilst uncovering the importance of friction, aesthetics, and stroke beautification to users. The observed participant behaviour and recommended tangible goals should enhance the development and evaluation of future systems.