Web fonts quickly gained popularity among practitioners. Despite their wide-spread usage and critical role in design, there is a lack of empirical research regarding how practitioners select web fonts and what problems they encounter in the process. To fill this knowledge gap, we took a mixed-method approach to examine the salient factors and common issues in the typeface selection process. To understand the landscape of the problem, we first analyzed adoption data for Google Fonts, a representative online fonts directory. Then, we interviewed practitioners regarding their experience selecting web fonts and the problems they encountered. Finally, we issued a follow-up survey to validate the qualitative findings. Our study uncovered how practitioners operationalized three salient factors—affordability, functionality, and personality—in the typeface selection process. Participants reported difficulty in finding typefaces that satisfy the functionality and personality needs. We discuss patterns that led to this difficulty and offered practical design guidelines that alleviated the identified issues.