The Western calendar was modified from Julian to Gregorian for better accuracy. The change deleted 10 days in October 1582 in Catholic countries and deleted 11 days in September 1752 in Britain and her colonies. By default,
Mathematica applies the British (American) version. There is an issue for

concerning dates after October 14, 1582 and before September 14, 1752. For British dates, the default gives the correct answer. For dates in Catholic countries, use the
Gregorian option for
Calendar.
In the default (Western American) calendar, dates in September 1752 were deleted:
Because it is a solar and lunar calendar (the year follows the seasons and the months keep track of the phases of the moon), the Jewish calendar has an extra leap month 7 times every 19 years. This leap month occurs in spring the month preceding Passover, so it is appropriate to count the Jewish months starting with Nisan, the month of Passover, as follows:
Since the Jewish year begins in the fall, this numeration of months will not always follow an increasing order; that is, later dates in the same year may have a smaller number for the month:
For this reason,

will still work with the
Calendar->Jewish option, but will not follow the same rules; for example, it will return a lexicographically smaller (smaller in the canonical
Mathematica ordering) number for a later date: