The role of computers and software as tool, manufacturer, collaborator, and artist in relation to human crafters has been heavily debated philosophically and practically. A creativity support tool for a specific creative domain is interdisciplinary, crossing fields of computational creativity, creativity support tools, procedural content generation, human-computer interaction, and potentially many others. This work aims to consolidate applicable research to domains with physical craft execution, as well as present an instance of a proactive and cooperative creativity support tool for the domain of machine embroidery pattern digitization, or simply digitizing. Proprietary software tools exist for digitizers, but auto-digitizing features — features that claim to automatically convert an image to a pattern — are widely disparaged in the industry, and novices and intermediate digitizers face a steep learning curve. The primary directive of this work is to ease that learning curve by helping suggest and caution the user about both the digital and physical best practices of the craft. In order to accomplish this task, the creativity support tool must successfully model machine embroidery such that it can be executed by embroidery machines, including basic operations, expert rules-of-thumb, and physical constraints, as well as interface with the user in a helpful and productive manner.