The issue is that virtualenv bundles pip 8.1.1, which doesn't know about python_version. It then tries to upgrade to the latest pip and setuptools, but that version isn't Python 3.5 compatible.
If you build the virtualenv with --no-download, or use venv instead of virtualenv, you'll get just pip 8.1.1, and setuptools 20.7.0. You can then explicitly upgrade them to setuptools < 51.3, as you describe. We could add a hack to virtualenv to specify the setuptools < 51.3 restriction. But given Ubuntu 18.04 is almost EOL, I'm tempted to just leave this one be. It has a workaround... ** Changed in: python-virtualenv (Ubuntu) Status: New => Fix Released ** Also affects: python-virtualenv (Ubuntu Xenial) Importance: Undecided Status: New -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1912248 Title: virtualenv on xenial: easy_install syntax error To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/python-virtualenv/+bug/1912248/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs