$ touch тест
$ ./python Tools/scripts/md5sum.py тест
d41d8cd98f00b204e9800998ecf8427e тест
$ LC_ALL=uk_UA.koi8u PYTHONIOENCODING=koi8-u ./python Tools/scripts/md5sum.py тест
d41d8cd98f00b204e9800998ecf8427e тест
$ LC_ALL=uk_UA.koi8u PYTHONIOENCODING=utf-8 ./python Tools/scripts/md5sum.py тест
d41d8cd98f00b204e9800998ecf8427e я┌п╣я│я┌
$ PYTHONIOENCODING=koi8-u ./python Tools/scripts/md5sum.py тест
d41d8cd98f00b204e9800998ecf8427e ����
$ PYTHONIOENCODING=latin-1 ./python Tools/scripts/md5sum.py тест
Traceback (most recent call last):
  File "/home/serhiy/py/cpython/Tools/scripts/md5sum.py", line 93, in <module>
    sys.exit(main(sys.argv[1:], sys.stdout))
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/home/serhiy/py/cpython/Tools/scripts/md5sum.py", line 90, in main
    return sum(args, out)
           ^^^^^^^^^^^^^^
  File "/home/serhiy/py/cpython/Tools/scripts/md5sum.py", line 39, in sum
    sts = printsum(f, out) or sts
          ^^^^^^^^^^^^^^^^
  File "/home/serhiy/py/cpython/Tools/scripts/md5sum.py", line 53, in printsum
    sts = printsumfp(fp, filename, out)
          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/home/serhiy/py/cpython/Tools/scripts/md5sum.py", line 69, in printsumfp
    out.write('%s %s\n' % (m.hexdigest(), filename))
    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
UnicodeEncodeError: 'latin-1' codec can't encode characters in position 33-36: ordinal not in range(256)