pip error while installing Python: “Ignoring ensurepip failure: pip 8.1.1 requires SSL/TLS”

Question

I downloaded the Python 3.5 source code and ran the following:

$ tar -xf Python-3.5.2.tar.xz
$ ./configure --with-ensurepip=upgrade
$ make
$ sudo make altins         


        

Answer 1

On Ubuntu 18.04 only this worked for me

sudo apt-get install libssl1.0

Answer 2

If you are using RedHat Enterprise Linux, you can use this:

yum install openssl-devel -y

Answer 3

CentOS:

If you didn't have openssl-devel at the time of installing python, pip 8.1.1 won't install. After installing openssl-devel, reinstall python. This time it should install pip just file.

Answer 4

You are most likely not compiling Python with SSL/TLS support - this is likely because you don't have the SSL development dependencies installed on your system.

Install the following dependency, and then re-configure and re-compile Python 3.5.

Ubuntu

apt-get install libssl-dev

In addition it is recommended to install the following.

apt-get install make build-essential libssl-dev zlib1g-dev libbz2-dev libsqlite3-dev

CentOS

yum install openssl-devel

In addition it is recommended to install the following.

yum install zlib-devel bzip2-devel sqlite sqlite-devel openssl-devel

Answer 5

CentOS or RHEL machine Python3(3.7.0) ssl not supported as of now.

pip installation supported with Python <=3.6

Answer 6

I tried to install Python 3.4.10 using asdf but got following error:

$ asdf install python 3.4.10
python-build 3.4.10 /home/br0ke/.asdf/installs/python/3.4.10
Downloading Python-3.4.10.tar.xz...
-> https://www.python.org/ftp/python/3.4.10/Python-3.4.10.tar.xz
Installing Python-3.4.10...
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 (Fedora 30 using python-build 1.2.15-2-g22c02022)

Inspect or clean up the working tree at /tmp/python-build.20191121110112.9959
Results logged to /tmp/python-build.20191121110112.9959.log

Last 10 log lines:
(cd /home/br0ke/.asdf/installs/python/3.4.10/share/man/man1; ln -s python3.4.1 python3.1)
if test "xupgrade" != "xno"  ; then \
    case upgrade in \
        upgrade) ensurepip="--upgrade" ;; \
        install|*) ensurepip="" ;; \
    esac; \
     ./python -E -m ensurepip \
        $ensurepip --root=/ ; \
fi
Ignoring ensurepip failure: pip 9.0.1 requires SSL/TLS

It may mean that I have too fresh OpenSSL version installed in my system and this version is not supported by Python I'm trying to build. I managed to install Python 3.4.10 on my Fedora 30 machine (has OpenSSL 1.1+ by default) using the following steps:

1. Temporary remove openssl-devel if it is installed as it will conflict with older version:

$ sudo dnf remove openssl-devel

2. Install compat OpenSSL 1.0 packages:

$ sudo dnf install compat-openssl10 compat-openssl10-devel

3. Build Python 3.4.10 (I use asdf but it should work with pyenv as well):

$ asdf install python 3.4.10

4. Remove compat library and install modern instead to be able to build something more fresh next time:

$ sudo dnf remove compat-openssl10-devel
$ sudo dnf install openssl-devel

Inspired by this workaround with help from Fedora community people.