I'm not sure if Python just relies on some other resource for this (i.e. a C function), but as of yesterday the correct upper case of ß is ẞ:

Official announcement in German:
http://www.rechtschreibrat.com/DOX/rfdr_PM_2017-06-29_Aktualisierung_Regelwerk.pdf

Small addition after I posted in excitement and now actually read the announcement: German now allows ẞ *as well as* SS when turning ß into upper case.

Although I'm not German, I'm rather pleased by this. Nevertheless I don't think we actually need to do anything yet.

I think it is more important that Python follows the standard Unicode behaviour. If and when Unicode recommend that 'ß'.upper() returns '\N{LATIN CAPITAL LETTER SHARP S}' then we should follow, until then we should treat it as no different from any other locale-specific difference. For example, 'i'.upper() returns 'I' instead of 'İ' as you would expect if you are Turkish.

Python doesn't make politic :-) Python implements Unicode standard. Python 3.7 currently uses Unicode 10.0:

haypo@selma$ ./python
Python 3.7.0a0 (heads/master:b903067, Jun 30 2017, 11:49:25) 
>>> unicodedata.unidata_version
'10.0.0'

It seems like Unicode 10 still uses "SS":

>>> 'ß'.upper()
'SS'

The German government has to change the Unicode standard :-) Please report this "bug" to the Unicode standard :-) So I closes this issue as "third party.