Josh Rosenberg added the comment:

It looks like between 3.4.3 and 3.5, datetime_best_possible changed from using 
_PyTime_gettimeofday with a _PyTime_timeval to using _PyTime_AsTimeval with 
struct timeval. The difference is that _PyTime_timeval appears to have been 
defined with a proper time_t for secs, where struct timeval is defined (on 
Windows) with a long which is still 32 bits on Windows, so we reintroduced the 
Y2K38 problem.

The bug was introduced while trying to support #22117: "Rewrite pytime.h to 
work on nanoseconds" in reve93eeadef0c3: 
https://hg.python.org/cpython/rev/e93eeadef0c3

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nosy: +josh.r

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