Inada Naoki <songofaca...@gmail.com> added the comment:

There is no strict guarantee.

I think ASCII, UTF-8, latin1 with surrogateescape guarantee roundtrip.

Other legacy encodings like cp932 may not roundtrip. But it is not a huge 
problem because only Windows use them typically.
On Windows:

* wchar_t is used in most case, instead of fsencoding
* fsencoding is now UTF-8 by default

In other words, if you are using legacy encoding on Unix, it may be not 
roundtripping.

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<https://bugs.python.org/issue17110>
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