AbstractIn Canvas and Qualtrics, a recent assignment feature enables learners (or survey participants) to upload digital files. While these have varying limits of file sizes, of file types, of file handling, identification or anonymization of file uploaders, and the level of sharing of uploaded files, it is useful to think of assignment possibilities to maximize this feature. This presentation provides preliminary instructional design for how to build effective assignments using the file upload feature. This session involves considerations like intellectual property, privacy rights, and proper handling of digital contents by learners and instructors. There are also considerations for data security and protections. Finally, there are discussions about memory limits for file uploads (within an online course), as well as digital preservation (whether the uploaded files are temporary and transient or semi-permanent or permanent, for learning purposes).