R. David Murray <rdmur...@bitdance.com> added the comment:

Since you parsed it as a string it is not really legitimate to serialize it as 
bytes.  (That will work if the input message only contains ascii, but not if it 
contains unicode).  You'll get the same error if you replace the garbage with 
the "’".  Using errors=replace is not crazy, but it hides the actual problem.  
Let's see what other people think :)

In theory you could "fix" this by encoding the unicode using the charset 
specified by the container.  I have no idea how complicated it will be do that, 
and it would be a new feature: parsing strings is specified to only work with 
ASCII input, currently.

I put "fix" in quotes, because even if you make text parts like this example 
work, you still can't handle non-text 8bit mime parts.  Is it worth doing 
anyway?

Really, message_as_string and friends should just be avoided entirely, maybe 
even deprecated.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue39384>
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