David Hess added the comment:

Concur with @sivert – the result of guess_extension() is non-deterministic 
between mimetypes module initialization.

$ python
Python 3.4.3 (default, Nov 17 2016, 01:08:31) 
[GCC 4.8.4] on linux
Type "help", "copyright", "credits" or "license" for more information.
>>> 
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpe
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpe
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpe
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpeg
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpeg
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpe
$ python -c 'import mimetypes;print(mimetypes.guess_extension("image/jpeg"))'
.jpg
$

----------
nosy: +dhess

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