Hi @rressler ...
I'm not sure what you mean. You've posted your question in the global Canvas Community website. Canvas is a Learning Management System (LMS) where schools (ranging from K-12 to higher ed...and even some other businesses) house their courses for students to take online. This Community site is a place to ask questions about Canvas, submit feature requests/ideas, review written and video tutorials about Canvas, join groups, and much more.
If you have a question about Canvas, we can try and answer that for you. But, I'm not sure what you mean by "free draw icon", "bounding box", and "pen icon" ... as these aren't things I'm familiar with inside of Canvas.
If you could help to clarify, that would be helpful...thanks!