Hello @MGEdD ...
I have also been recently experiencing this same issue. And, like you, I've tried multiple times to upload a new image, but it doesn't show up right away. Usually, I've had to wait a good day or two for the image to change. I have even reported this to the Canvas Help Desk staff. It's strange because from their end, they see that I uploaded a new image, but on my end, I don't see it immediately. I'm not sure if it's a browser cache issue or not. One suggestion they had was to completely shut down your computer and then re-start to see if that fixes it. It might be worth a shot.
