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I've narrowed it to this example, it passed on 2.7-alpine, but fails on 3.5-alpine and 3.6-alpine
FROM python:3.6-alpine
RUN apk update
RUN apk add git
RUN mkdir /bug
RUN cd /bug && ln -s /broken_path/to_nowhere broken
RUN python -c "import shutil; shutil.copytree('/bug', '/temp', symlinks=True)"
EDIT:
After playing around, I've nailed it to this command failing
>>> os.chmod('/bug/broken', 511, follow_symlinks=False)
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
OSError: [Errno 95] Not supported: '/bug/broken'