Digital drawing can foster learning, but only if the drawing is of sufficient quality. Hence, the focus of the present study was to investigate whether and how two types of drawing support may foster drawing quality and, in turn, learning outcomes. To this end, participants (N = 156) were randomly assigned to one of four conditions, in which they either just read text (control), were prompted to make a free-hand representational drawing (unsupported drawing), or they were additionally supported in their drawing efforts because a background (global support) or single elements for the drawing (local support) were already provided. Learning outcomes were assessed by means of recognition, transfer, and a drawing test. Results revealed that students from all three drawing conditions (unsupported, global, and local support) scored better on the transfer and drawing tests than the control condition. Both types of drawing support did neither increase drawing quality nor learning in comparison to unsupported drawing. Reasons for the latter findings are discussed.