Serhiy Storchaka <storchaka+cpyt...@gmail.com> added the comment:

It works to me (after fixing the assertion).

What Python version do you use? In Python 2 u'\uDD00' is encodable to UTF-8, so 
the error handler is not called. u'\uDD00yz'.encode('utf8') gives 
'\xed\xb4\x80yz'.

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nosy: +serhiy.storchaka

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<https://bugs.python.org/issue38800>
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