Ethan Furman added the comment:

This is not a regression.  json only deals with standard types (int, str, 
etc.), and Enum is not a standard type.

Enum was introduced in 3.4, so corresponding changes were made to json to 
support int and float subclasses, of which IntEnum is one.

In other words, this was a bug that no one noticed for many many releases, and 
I'm not sure we should fix it in 2.7 now.

Arguments for fixing?

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<http://bugs.python.org/issue22297>
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