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I am trying to install python version 3.4.10 via pyenv but I get the error Ignoring ensurepip failure: pip 9.0.1 requires SSL/TLS. For python versions after 3.4.10 (e.g.: 3.5.9), it did succeed however. I tried following the instructions both on this StackOverflow post and on the official pyenv Common Build page and it always returned the following error message:

Last 10 log lines:
(cd ~/.pyenv/versions/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.exe -E -m ensurepip \
                        $ensurepip --root=/ ; \
        fi
Ignoring ensurepip failure: pip 9.0.1 requires SSL/TLS
N.Berghmans
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1 Answers1

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I came across this post which specified uninstalling OpenSSL v1.1 and caused pyenv to install the correct version (1.0.2) of OpenSSL to compile python with.

The solution that worked for me was: 

brew uninstall --ignore-dependencies openssl@1.1
pyenv install 3.4.10

Attention: This may cause some libraries to break that depend on OpenSSL, so either re-install the latest version afterwards using brew install openssl or execute the following to have version 1.0.0 via brew: 

 brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
N.Berghmans
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