Not sure if this helps (I don't have Windows to check) but there are unresolved issues in the Linux builds that may affect you here also, see https://github.com/OpenSmalltalk/opensmalltalk-vm/pull/562. Suggestion - try checking out the fix_include_order branch and see if it works, or check out any older version prior to aafcb78371c7e576073a8dbf2f1f32667568e05e.