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Since ensurepip needs to manipulate sys.path, I ended up running the "-m ensurepip" using the venv Python in a subprocess. This both avoids side effects on the current process and gets ensurepip the right target directory settings automatically.
Rather than reopening this (which is part of tracking the feature integration for the beta), I opened bpo-19694 to cover the stable buildbot that is objecting to the new venv test (most of the others seem happy with it)