OpenSSL update by brew broke python

[awgymer]

On Mac, brew has updated the openssl install to openssl@3 and this seems to have broken all my python installs from pyenv:

ImportError: dlopen(/Users/me/.pyenv/versions/3.11.4/lib/python3.11/lib-dynload/_ssl.cpython-311-darwin.so, 0x0002): Library not loaded: /usr/local/opt/openssl@1.1/lib/libssl.1.1.dylib

What is the correct/best way to update my pyenv managed python installs so that they work with the new openssl?

[brunns]

Does pyenv install -f 3.11 help?

[awgymer]

I was staring at this for a hot minute before I saw the edit.

That seems to have done the trick (and doesn't break venvs which is nice).

I got some build warnings about tcl missing libs which I think is a similar brew issue but I'll work those out later, it just built without tk support which I didn't need this second.

[brunns]

If you do need tk, brew install tcl-tk followed by another forced install should do the trick for you.

[digeomel]

I don't know if this is the same issue, but on Ubuntu 22.04.5 LTS with homebrew OpenSSL is installed here:

/home/linuxbrew/.linuxbrew/etc/openssl@3

and none of the commands below as per the wiki work for me:

CPPFLAGS="-I/home/linuxbrew/.linuxbrew/etc/openssl@3/include" \
LDFLAGS="-L/home/linuxbrew/.linuxbrew/etc/openssl@3/lib" \
pyenv install 3.10

LDFLAGS="-Wl,-rpath,/home/linuxbrew/.linuxbrew/etc/openssl@3/lib" \
CONFIGURE_OPTS="--with-openssl=/home/linuxbrew/.linuxbrew/etc/openssl@3" \
pyenv install 3.10

LDFLAGS="-Wl,-rpath,/home/linuxbrew/.linuxbrew/etc/openssl@3/lib" \
CONFIGURE_OPTS="--with-openssl=/home/linuxbrew/.linuxbrew/etc/openssl@3 --with-openssl-rpath=auto" \
pyenv install 3.10

I keep getting:

Downloading Python-3.10.18.tar.xz...
-> https://www.python.org/ftp/python/3.10.18/Python-3.10.18.tar.xz
Installing Python-3.10.18...
Traceback (most recent call last):
  File "<string>", line 1, in <module>
  File "/home/myuser/.pyenv/versions/3.10.18/lib/python3.10/ssl.py", line 99, in <module>
    import _ssl             # if we can't import it, let the error propagate
ModuleNotFoundError: No module named '_ssl'
ERROR: The Python ssl extension was not compiled. Missing the OpenSSL lib?

Please consult to the Wiki page to fix the problem.
https://github.com/pyenv/pyenv/wiki/Common-build-problems


BUILD FAILED (Ubuntu 22.04 using python-build 20180424)

Inspect or clean up the working tree at /tmp/python-build.20250618194801.260612
Results logged to /tmp/python-build.20250618194801.260612.log

Last 10 log lines:
	LD_LIBRARY_PATH=/tmp/python-build.20250618194801.260612/Python-3.10.18 ./python -E -m ensurepip \
		$ensurepip --root=/ ; \
fi
Looking in links: /tmp/tmpcoi3wlk4
Processing /tmp/tmpcoi3wlk4/setuptools-65.5.0-py3-none-any.whl
Processing /tmp/tmpcoi3wlk4/pip-23.0.1-py3-none-any.whl
Installing collected packages: setuptools, pip
  WARNING: The scripts pip3 and pip3.10 are installed in '/home/myuser/.pyenv/versions/3.10.18/bin' which is not on PATH.
  Consider adding this directory to PATH or, if you prefer to suppress this warning, use --no-warn-script-location.
Successfully installed pip-23.0.1 setuptools-65.5.0