Installing new versions of Python on Cygwin does not install Pip?

cel self-answered this question in a comment above. For posterity, let’s convert this helpfully working solution into a genuine answer.

Unfortunately, Cygwin currently fails to:

• Provide pip, pip2, or pip3 packages.
• Install the pip and pip2 commands when the python package is installed.
• Install the pip3 command when the python3 package is installed.

It’s time to roll up our grubby command-line sleeves and get it done ourselves.

What’s the Catch?

Since no pip packages are currently available, the answer to the specific question of “Is pip installable as a Cygwin package?” is technically “Sorry, son.”

That said, pip is trivially installable via a one-liner. This requires manually re-running said one-liner to update pip but has the distinct advantage of actually working. (Which is more than we usually get in Cygwin Land.)

pip3 Installation, Please

To install pip3, the Python 3-specific version of pip, under Cygwin:

$ python3 -m ensurepip

This assumes the python3 Cygwin package to have been installed, of course.

pip2 Installation, Please

To install both pip and pip2, the Python 2-specific versions of pip, under Cygwin:

$ python -m ensurepip

This assumes the python Cygwin package to have been installed, of course.