thank you P.B. Lecavalier!
I greatly appreciate your response!
Perhaps this can guide the cygwin packaging in te future

I was missing ` python-setuptools-wheel` but I had installed the `
python-setuptools-wheel`

Now I have success

$  python3 -m ensurepip
Looking in links: /tmp/tmpy457n2k6
Requirement already satisfied: setuptools in
/usr/lib/python3.9/site-packages (75.8.0)
Requirement already satisfied: pip in
/usr/local/lib/python3.9/site-packages (25.0.1)

On Fri, Apr 18, 2025 at 4:38 AM Philippe Baril Lecavalier via Cygwin <
cygwin@cygwin.com> wrote:

> Try these, seemingly not pulled from installing python39:
>
>     python-setuptools-wheel
>     python-pip-wheel
>
> I confirm the issue with a fresh install with python3{8,9}. pip is
> provided, but `ensurepip` gives that error. I think it should be the
> opposite on a basic python install: No pip package should be present
> or enforced, but ensurepip should be guaranteed to work to bootstrap
> pip if you so desire.
>
> --
> P.B. Lecavalier
>
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