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I have no idea why selecting Photoshop as the always-open-with app resulted in the correct ProgId begin set for .tif but not for .jpg, .png, and .raw, but it doesn't seem possible to fix. At this point, I started looking at other extensions that I had not touched like .tga. I never set a always-open-with app for .tga, so it did not have a UserChoice key. Instead, .tga's extension key defined the associated type like so:

So we can't remove the UserChoice key, and we can't update UserChoice.ProgId to the correct value... what now?

I have no idea why selecting Photoshop as the always-open-with app resulted in the correct ProgId being set for .tif but not for .jpg, .png, and .raw, but it does not seem possible to fix. At this point, I started looking at other extensions that I had not touched like .tga. I never set a always-open-with app for .tga, so it did not have a UserChoice key. Instead, .tga's extension key defined the associated type like so:

So we can't remove the UserChoice key, we can't update UserChoice.ProgId to the correct value, and we can't override the file type specified by UserChoice.ProgId... what now?

You can refer to the this flowcart about how Windows 10 chooses an icon for a file. I came up with this by making changes in the registry and observing the results.

You can refer to the flowchart below about how Windows 10 chooses an icon for a file. I came up with this by making changes in the registry and observing the results.

(click to enlarge)

Registry changes wont take effect until explorer.exe is restarted/refreshed. You can use Task Manager to kill and restart explorer.exe, or you can use DesktopRefresh.exe (Google it, I can only post 2 links).

Registry changes wont take effect until explorer.exe is restarted/refreshed. You can use Task Manager to kill and restart explorer.exe, or you can use DesktopRefresh.exe.