Well, I wouldn't immediately celebrate "Got it!" 😄 but yes, I can reproduce this in Squeak 5.3 (64-bit) with the VM 202003021730. So, what does this behavior tell us? At least, it is releated to some kind of memory management. Renaming "Squeak.exe" to something else or using "SqueakConsole.exe" or changing the VM to 202011120327 ... all options still show that bug in that "broken" image.

There is something wrong with module loading. Is there some interference between Squeak's object memory and how modules are loaded? Maybe take a look at how primitive 571 is implemented. (SmalltalkImage >> #unloadModule:)

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