@BradleyChungTwo considerations here. It is possible this is an issue because the assignment submission was created with the desktop version of Word and the anchors for images don't always transfer well over to the web version of Word, which is embedded in the Assignment viewer of Teams. If students are going to be submitting images to the assignment, you might want to consider using a Class Notebook page. Create a blank page with a title and instructions for students to insert images of their work then attach it to the assignment. You will then be able to annotate and add comments while not running into as many issues with positioning the images. To help the issue if you are still using a Word document, you might want to try using a similar strategy where you assign a blank Word document with a title and the instructions to insert images. Click on the three dots beside the document when you add it to the assignment and change to 'Students edit their own copy'. Tell students to use the online version of Word to edit the document and insert the images. I have found that this is less of an issue when the images were added using Word Online to start with.