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The test runner split -Idirectory on a hardcoded ":", so on Windows an absolute path such as -IV:/foo/lib was broken into "V" and "/foo/lib". The tail only resolved by accident when the current drive matched. File::PATH_SEPARATOR is the right delimiter, matching ruby -I itself. This is the same class of bug as the test-syntax-suggest -I fix in commit 3c7a4c174f, which replaced ":" with $(PATH_SEPARATOR) in common.mk. Makefiles only pass relative paths, so this stayed latent.