We contribute an in-depth analysis of the characteristics of traditional stippling and relate these to common practices in NPAR stippling techniques as well as to the abilities and limitations of existing printing and display technology. In our work we focus specifically on the properties of stipple dots and consider the dimensions and attributes of pens and paper types used in artistic practice. With our analysis we work toward an understanding of the requirements for digital stippling, with the ultimate goal to provide tools to artists and illustrators that can replicate the stippling process faithfully in the digital domain. From the results of our study we provide a dataset for use in new example-based stippling techniques, derive a taxonomy of characteristics and conditions for the reproduction of stippling, and define future directions of work.