Ammar Askar added the comment:

The 86,399 upperbound comes from this line (max_fold_seconds=86400):

https://github.com/python/cpython/blob/master/Modules/_datetimemodule.c#L4277-L4278

The bug is introduced as part of the fold detection in this commit: 
https://github.com/python/cpython/commit/56376cacd2a0f6af834fe4d2a20b1a1095afb26f

Window's locatime_s function gives an EINVAL error when time is less than 0. 
Which is where the OSError comes from.

https://msdn.microsoft.com/en-us/library/a442x3ye.aspx

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