I face the same issue, running OSX 10.10.2 and python 3.4.2. Most recently I created a virtual environment in a debian wheezy machine with python 3.4.3 and also ended up with an older version of pip than available. had to upgrade pip.

I've been upgrading pip within the virtual environment to 6.1.1 from 6.0.8 manually, because I'm o.c.d about software library versions that way - and yes, I am upgrading my python 3 version to 3.4.3 right now. Anyway, my system's python3-pip is the latest version 6.1.1, so I've also wondered why pyvenv creates a new virtual environment and loads it with old pip.

I haven't noticed anything bad happen in any of the virtual environments due to upgrading pip, (but on the flip side, I haven't noticed anything good either) Apparently the new pip is faster -- didn't notice, and outputs less junk on successful installs because user's don't care -- also didn't notice, probably because i'm one of those that don't care, and also comes with a state-of-the art coffee machine capable of latte art to boot!!! -- still waiting on sudo pip install latte to finish :(

So, to answer your question, it is definitely possible, and probably advisable to upgrade, because apparently the new pip fixes some bugs and goes faster, but I guess the speed up isn't that major, and the bug fixes don't affect all that many people (I've never faced a bug with my usage of the old pip).

You can link to system site-packages using the flag --system-site-packages when you create a new virtual environment, like this

pyvenv myenv --system-site-packages

This will link to your system wide version of pip, and would remove the annoyance that is manually upgrading pip on every virtual environment, but if you do this, then is your virtual environment all that virtual?

update: following my rant above, I went into the venv package's source to dig. pip is set up by a method called _setup_pip in the file __init__.py, line 248

def _setup_pip(self, context):        """Installs or upgrades pip in a virtual environment"""        # We run ensurepip in isolated mode to avoid side effects from        # environment vars, the current directory and anything else        # intended for the global Python environment        cmd = [context.env_exe, '-Im', 'ensurepip', '--upgrade',                                                    '--default-pip']        subprocess.check_output(cmd, stderr=subprocess.STDOUT)

So, venv seems to be calling ensurepip from the shell using the subprocess module.

One more minute of google-fu gave me this from the documentation for ensurepip.

ensurepip.version()

Returns a string specifying the bundled version of pip that will be installed when bootstrapping an environment.

So, from the command line, the following code:

$ python3 -c 'import ensurepip; print(ensurepip.version())' 6.0.8

displays my current pip that will be bootstrapped with ensurepip.

I guess we're stuck with the old version of pip for every new install until ensurepip gets upgraded, as I can't find a way to upgrade the version of pip that comes with ensurepip

Newer

If you want to "hotpatch" your installed python, just modify the versions listed in ensurepip/__init__.py and replace the two files in ensurepip/_bundled. You can find this location by running find * | grep ensurepip from the directory where python is installed. On macOS with Homebrew, this is the location: /usr/local/Cellar/python/3.7.1/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ensurepip

You will also want to delete the ensurepip/__pycache__ directory that contains the .pyc files.

My older, build-time fix:

You are able to update the bundled versions of pip and setuptools by patching Python before building it from source. The following patch will update the bundled versions of pip and setuptools to the current available today. You will want to invoke configure with the following option: --with-ensurepip=upgrade

Those whl files are downloaded from PYPI here:

https://pypi.org/project/pip/#files

https://pypi.org/project/setuptools/#files

diff -ru Python-3.7.1/Lib/ensurepip/__init__.py Python-3.7.1.new/Lib/ensurepip/__init__.py--- Python-3.7.1/Lib/ensurepip/__init__.py  2018-10-20 06:04:19.000000000 +0000+++ Python-3.7.1.new/Lib/ensurepip/__init__.py  2018-11-27 02:36:19.301655008 +0000@@ -8,9 +8,9 @@ __all__ = ["version", "bootstrap"]-_SETUPTOOLS_VERSION = "39.0.1"+_SETUPTOOLS_VERSION = "40.6.2"-_PIP_VERSION = "10.0.1"+_PIP_VERSION = "18.1" _PROJECTS = [     ("setuptools", _SETUPTOOLS_VERSION),Only in Python-3.7.1/Lib/ensurepip/_bundled: pip-10.0.1-py2.py3-none-any.whlOnly in Python-3.7.1.new/Lib/ensurepip/_bundled: pip-18.1-py2.py3-none-any.whlOnly in Python-3.7.1/Lib/ensurepip/_bundled: setuptools-39.0.1-py2.py3-none-any.whlOnly in Python-3.7.1.new/Lib/ensurepip/_bundled: setuptools-40.6.2-py2.py3-none-any.whl

If you're lucky, you can bump it up with a Python patch.

Is your Python outdated? This is using macports, but any of brew, apt should do.

port outdated

python36                       3.6.9 < 3.6.10

Let's fix that:

sudo port upgrade python36

And now... drumroll, in my newly-recreated venv, it seems that the Python patch has brought along the latest pip.

pip --version shows 20.0.2, it was at 18 previously and that's precisely what it was complaining about in the venv.

This is after spending a ludicrously long amount of time trying to figure out how to update my user-level Python 3.6 version of pip, on a mac where, of course, if you quit the virtualenv you are at Python 2.7 and where Python 3.6, installed through macports, doesn't seem to have a pip command to work with, until you build a venv.

From looking at /opt/local/Library/Frameworks/Python.framework/Versions/3.6, where macports puts things, I suspect Utknonos is on to something, so +1.

There really should be something a bit more obvious, like a pip-system-selfupdate command or a pip36 that comes along with python36. Especially considering that a search of pip upgrade will return tons of hits on anything but this subject.

Note: after my update, even though Python has been updated

(venv)$ pwd/opt/local/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6(venv)$ grep PIP_VERSION ensurepip/__init__.py_PIP_VERSION = "18.1"(venv) $python --versionPython 3.6.10(venv) $pip --versionpip 20.0.2 from .../venv/lib/python3.6/site-packages/pip (python 3.6)