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CalibreSpy is "special" in that it is designed to be run in a multi-user environment using the identical Calibre Library metadata.db simultaneously via CLI rather than from the GUI itself. Because of that, when you install CalibreSpy, it uses the current Calibre configuration directory to unzip its icons into "...\calibre\plugins\calibrespy_cli\images" to enable CalibreSpy to function when it is running via CLI and not from the Calibre GUI. Calibre "standard" functionality is not guaranteed to exist when Calibre is not running, of course, hence CalibreSpy's workaround for the image directory to enable CLI execution.
Whenever Calibre starts, CalibreSpy checks to see if the "current" Calibre config directory has changed since "the last time" Calibre was started. If so, CalibreSpy extracts the icon files to the "new" "...\calibre\plugins\calibrespy_cli\images".
I am not clear at all why you encountered this problem giving that the above behavior should have re-extracted the images automatically and transparently unless there was a "perfect storm" of events that led to it. Assuming that was the case, I am going to add a "perfect storm test" to CalibreSpy and have it extract the icon images (again) if that occurs.
DaltonST
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