I've provided you a simple learning object that we are using to copy from. I failed to mention in my first post that we are using a customised page type called cover page.
I have testing importing both the customised cover page and a standard title page into a new learning object and the pages import, but no images are imported into the media folder for the new learning object.
Yes, there are errors in the dev console, which I've attached.
We are also on the latest version of 3.9. It was transitioning to this version in which the issue appeared.