calibre does not have an "Open with external program" option.
It does have "Export file" and "Replace ____ with file".
You do not want to update a JPG with the contents of a PNG anyway, that is a recipe for disaster...
This is exactly why I specified in my original reply:
- Open ebook in calibre's Editor
- Export image.
- Do xxx to image.
- Import new image into book.
- Update references of the old image, to refer to the new image instead. (This goes without saying... right???)
You need the Editor, because it can handle the work of importing and deleting new EPUB resource files, and applying changes to all the text files that might invoke that image.