Nick Coghlan added the comment:

After further consideration, I realised there's an important difference between 
this case and the hash randomisation case: having the "-E" switch imply hash 
randomisation was OK, but having it imply HTTPS certificate verification after 
the system administrator has explicitly turned it off is going to cause 
problems.

The system administrator controlled configuration file gets around that by not 
relying on the interpreter's environment variable based configuration support.

As a result, I've now recommended pursuing the configuration file based 
approach, with a PEP to standardise the precise name, format and semantics for 
the configuration file: https://bugzilla.redhat.com/show_bug.cgi?id=1173041#c8

Redistributors would opt-in by patching their system Python to implement that 
informational PEP, rather than the feature appearing in upstream CPython itself.

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<http://bugs.python.org/issue23857>
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