This paper examines the development process of a library Blackboard course by a Research & Instruction Librarian at the University of Mississippi over the course of one summer. The Library Skills and Orientation course sought to address two issues: limited first-year instruction capabilities and underdeveloped skillsets in upper-level students. It was designed to replace first-year instruction where able and supplement subject-specific instruction where needed. Pursuing new online learning initiatives can be a tough sell, however, when many institutions are attempting to return to normal in-person routines after two years of forced virtual work due to the pandemic. This paper discusses not only the obstacles faced by the librarian who created the course – specifically related to time constraints, librarian inexperience, and buy-in – but also opportunities that other academic libraries can take advantage of to expand online learning initiatives post-Covid.