A system, method and computer program product for managing typesetting of digital ink structured content on computing devices. Each computing device has a processor and at least one system application for recognizing handwriting input under control of the processor. The system application determines dimensional information of at least digital ink text elements of structured content, calculates a first font size for each typeset ink text element respectively corresponding to the digital ink text elements based on at least part of the dimensional information, categorizes the typeset ink text elements into one or more categories of the structured content, determines a second font size for each typeset ink text element based on the first font size of each typeset ink text element of the respective category, and display, on a display associated with the computing device, the typeset ink text elements at the respective determined second font sizes.