I can still reproduce it every time so I don't know why you wouldn't be able to.
I am unable to send you the application being tested as I am testing an extension to the application and don't have the license to share the main application. I will try it with something like Notepad.
Also, I noticed that in my Regions folder, there are two files for every region that isn't getting updated. However, the one region that I have not renamed (so the one that is still being updated correctly) only has one file in the folder, the .PNG file. The others have a file by the same name as the .PNG file, but does not have an extension. Any insight into this?
For example, I have
region1.png
region1
region2.png
region2
region3.png
From this list, only region3 is getting updated. Notice it is the only region that doesn't have a file without an extension.