Python referencing old SSL version

Question

I have a Dropbox upload script on an old nas box I have, recently I've been getting the following error

SSL certificate error: [Errno 1] _ssl.c:504: error:0D0890A1:asn1 encoding routines:ASN1_verify:unknown message digest algorithm

I think this is due to openssl being out of date on the box

So I download openssl, built it from source and installed it, now when I run the following it appears to be updated correctly.

openssl version
OpenSSL 1.0.1h 5 Jun 2014

But it would appear Python is still referencing an old version, how would I update this?

python -c "import ssl; print ssl.OPENSSL_VERSION"
OpenSSL 0.9.7m 23 Feb 2007

Answer 1

Got this working after several days. MAC OS X El Captian or greater

 sudo rm -rf /Library/Frameworks/Python.framework/Versions/2.7
 sudo rm -rf "/Applications/Python 2.7"
 cd /usr/local/bin/
 ls -l /usr/local/bin | grep '../Library/Frameworks/Python.framework/Versions/2.7' | awk '{print $9}' | tr -d @ | xargs rm
 brew uninstall python
 brew uninstall openssl
 brew link --force openssl

Now install python and openssl again using brew.

 brew install openssl
 brew install python --with-brewed-openssl

Add the following to the PATH in ~/.bash_profile on your MAC

 vi ~/.bash_profile
 export PATH=/usr/local/opt/openssl/bin:/usr/local/opt/python/libexec/bin:$PATH

restart the terminal

 python --version (verify if it is picking up the right version)
 openssl version -a (verify if it is picking up the right version)
 python -c "import ssl; print ssl.OPENSSL_VERSION"

(note: if you installed Python3, you'll have to update the print syntax in the inline compiler step)

python -c "import ssl; print(ssl.OPENSSL_VERSION)"

should give you the latest version OPEN SSL version

Answer 2

2018 on MacOS
I tried with the other answers without success:

• The --with-brewed-openssl option gives Warning: python: this formula has no --with-brewed-openssl option so it will be ignored!
• and the command brew link openssl --force gives Warning: Refusing to link: openssl

---

I got it working with

brew install openssl
brew install python@2

Then

openssl version

and

python -c "import ssl; print ssl.OPENSSL_VERSION"

gave me the same OpenSSL version.