Okay, I believe I have figured out the exact issue now. The issue only persists after a group of objects has been rotated and their selection box changes to fit over the grouped items. When you select an individual shape, the selection box retains its normal functionality and resizes correctly. Normal Functionality: <a href="https://gfycat.com/BothWhisperedAlligator" rel="nofollow">https://gfycat.com/BothWhisperedAlligator</a> However when a multitude of shapes are selected, when resizing the shapes based on the new grouped selection box, each individual shape will instead resize localized to their own selection boxes. Rotational Functionality: <a href="https://gfycat.com/PossibleCoolKusimanse" rel="nofollow">https://gfycat.com/PossibleCoolKusimanse</a> Rotational Functionality 2: <a href="https://gfycat.com/GreatImportantBedlingtonterrier" rel="nofollow">https://gfycat.com/GreatImportantBedlingtonterrier</a> And here is a quick image to better explain the issue than what I've managed to describe: The user sees the bounding box in Green . The Blue bounding boxes are invisible, but are the original bounding boxes for the shapes. Resizing the shapes via the Green Bounding Side #2 will stretch the shapes in a preview towards the Green Side #2 Directional represented by the green arrow. It will function as expected. However, once you accept the changes and let go of the selection, the shapes are actually changed by their own bounding boxes, the Blue Side #2 Directional. So instead of resizing to the East, they resize to the North East in this picture. I hope I explained myself well enough, my apologies if it is confusing. Additionally here is a pastebin of the console during the period of time where I discovered the issue. I've tried to minimize the irrelevant data by changing the default page to my debug page and doing as little as I could to properly recreate the issue.