This isn't a bug! CanYouHandleThisFile is only called for extensions OTHER than the registered extension, e.g. to open self-extracting EXE archives.
Its bug

(( or very not logically.
Because users register many same externsion (as EXE, CAB, 7z, Img, or other) in Wincmd.ini on different plugins. Its human logic. (If I needed in some task, I tel computer how to it is done).
Sample:
7z arhives. User can handle this archive in 2 special 7z plugins and Multiarc. And same time preffered plugin can not handle plugin, but it handled other plugin.
if I write registration as:
7z=223,%COMMANDER_PATH%\plugins\wcx\packer_plugins\MA\Multiarc.wcx
7z=495,%COMMANDER_PATH%\plugins\wcx\packer_plugins\7zip\7zip.wcx
7z=223,%COMMANDER_PATH%\plugins\wcx\packer_plugins\7z\7z.wcx
Its correct record in wincmd.ini, after reading help file.
I say TC: Try first plugin, if he cannot handle, try second, if secon cannon handle, try third, if third cannot handle, show error message (or do nothing).
Its logically, but not work

, because TC not call CanYouHandleThisFile.
TC direct call first plugin, function return _Error_, and TC not call other plugins.
But plugin frankly say "TC! I Do Not Handle This File". But TC not ask this, and, as finish show error.
But if I write like this
7z_=223,%COMMANDER_PATH%\plugins\wcx\packer_plugins\MA\Multiarc.wcx
7z_=495,%COMMANDER_PATH%\plugins\wcx\packer_plugins\7zip\7zip.wcx
7z_=223,%COMMANDER_PATH%\plugins\wcx\packer_plugins\7z\7z.wcx
For iterate via plugins for handle arhive and this work, but not logically.
In this case TC serch direct match, not found, and from first registration record Enum plugs, and call CanYouHandleThisFile, plugin say "TC! I Do Not Handle This File" and TC
process other plugin.
On My opinion, registration in wincmd.ini many same extension and correct choice plugin reduse process time, and clean settings.
Many users ask how to use MultiArc plugin if InnoUnpaker plugin cannot handle arhive file, and users register plugin in Wincmd.ini on EXE extension.
For EXE externsion, if it self extracted Installation, I use Multiarc, Innounpaker, IETotal. If self extracted arhive Multiarc and other plugins, and I must write different, abstract, extension for register plugins.
Extension IMG it good sample of neded call, its picture, ISO Image, FDD image, HDD image, or special unknow for TC plugin format. And TC have more one plugin for handle this format.
P.S. maybe start topic for needed changes and bugs in plugin API? For fix, collect and realization in future versions.