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Upgrading pyopenssl with pip was not working as none of the commands related to to pip was working for me. By upgrading pyopenssl with easy_install, above problem can be solved.

sudo python -m easy_install --upgrade pyOpenSSL

credit @delimiter (Answer)

Update your pyopenssl module:

$ sudo pip install -U pyopenssl

I experienced the same issue recently and after few hours investigation, I found out that it was caused by New cryptography 2.0 upgrade. This upgrade will break many packages using pyopenssl (like Sentry, Google Analytics and etc). Just downgrade it to 1.9 will solve the problem.

Be cautious if you are using "pip install -U", it will automatically upgrade packages that are not listed in requirements.txt.

I had a similar error:

    from OpenSSL import rand, crypto, SSL

  File "/usr/local/lib/python3.5/dist-packages/OpenSSL/SSL.py", line 112, in <module>

    SSL_ST_INIT = _lib.SSL_ST_INIT

AttributeError: module 'lib' has no attribute 'SSL_ST_INIT'

and none of the other answers could fix it, because pip could not install anything. Instead, what I did was this from the terminal first:

sudo rm -r /usr/local/lib/python3.5/dist-packages/OpenSSL

Then reinstalled pyopenssl with pip:

sudo pip install pyopenssl

and everything was gravy.

In my case, the problem was that the package was installed in root directories, and I was executing the script which asked for pyopenssl with my Linux user forvas. And that user can't use the libraries installed in root.

So first I had to remove the package with aptitude or apt-get.

sudo aptitude purge python-openssl

Therefore, I had to install the package again, but taking into account the user who is executing the script which is asking for the library. Take a look to where the library is installed depending on the Linux user and the argument --user of pip.

Case 1

forvas@server:$ pip install pyopenssl

Could not install packages due to an EnvironmentError:

[Errno 13] Permission denied: '/usr/local/lib/python2.7/dist-packages/OpenSSL'

Consider using the --user option or check the permissions.

Case 2

forvas@server:$ sudo pip install pyopenssl

/usr/local/lib/python2.7/dist-packages/OpenSSL/*

/usr/local/lib/python2.7/dist-packages/pyOpenSSL-17.5.0.dist-info/*

Case 3

forvas@server:$ sudo pip install --user pyopenssl

/home/forvas/.local/lib/python2.7/site-packages/OpenSSL/*

/home/forvas/.local/lib/python2.7/site-packages/pyOpenSSL-17.5.0.dist-info/*

Case 4

root@server:$ pip install pyopenssl

/usr/local/lib/python2.7/dist-packages/OpenSSL/*

/usr/local/lib/python2.7/dist-packages/pyOpenSSL-17.5.0.dist-info/*

Case 5

root@server:$ pip install --user pyopenssl

/root/.local/lib/python2.7/site-packages/OpenSSL/*

/root/.local/lib/python2.7/site-packages/pyOpenSSL-17.5.0.dist-info/*

Conclusion

My problem was that the library was installed in the directories of the case 5.

Solution

• Uninstalling the package.




• As I'm executing the script with Linux user forvas, I was able to reinstall the package rightly with the options 2 or 4 (in which the library is available for all Linux users) or more accurate, the option 3 (in which library is only available for Linux user forvas).

My problem was caused by the version of Python openssl that was in /usr/lib/python2.7/dist-packages/.

dpkg -l | grep openssl showed:

ii  python-openssl                                0.15.1-2build1                               all          Python 2 wrapper around the OpenSSL library

I removed it using sudo apt-get remove python-openssl. I then ran the following to install the distribution version of pip.

curl -o ./get-pip.py https://bootstrap.pypa.io/get-pip.py

sudo python2 ./get-pip.py

pip --version now displays:

pip 18.0 from /usr/local/lib/python2.7/dist-packages/pip (python 2.7)

I was then able to perform the necessary pip install I was trying to complete.

I was seeing similar python stack dump on the console of my Ubuntu 16.04 VM when I tried ssh into the VM.

    SSL_ST_INIT = _lib.SSL_ST_INIT

AttributeError: 'module' object has no attribute 'SSL_ST_INIT'

Pip reported that pyopenssl was not installed.

I had to do this instead:

$ apt install --reinstall python-openssl

I did this which helped:


$ easy_install -U pip
$ easy_install -U pyOpenSSL


I had the same problem on Ubuntu 16.04, but with the following twist: when virtualenv was activated (. venv/bin/activate before running celery workers with pysolr, requests, etc in my case) - everything worked perfectly, but when I ran celery from command line using full paths, and python paths - there was a problem (and same problem running from supervisord ). Also, if important, virtualenv has been bundled elsewhere on the machine with same Ubuntu version.

Solution was simple: adding /full/path/to/venv/bin to PATH ( as advised here https://serverfault.com/questions/331027/supervisord-how-to-append-to-path ) solved this.

Unfortunately, I have not yet pin-pointed what kind of update caused this, but hopefully this may help someone.

My solution was a lot more simplistic after these other solutions not working for me. Anything I tried to install/uninstall via pip returned the same error and stacktrace.

I ended up trying to update pip via pip3 and it worked flawlessly:

pip3 install --upgrade pip

I went back to using pip and everything worked correctly. I did notice that it was referencing Python 3.6 when running the pip commands though.

# pip install pyopenssl`enter code here`

Requirement already satisfied: pyopenssl in /usr/lib64/python3.6/site-packages (18.0.0)



<snipped>



Requirement already satisfied: pycparser in /usr/lib64/python3.6/site-packages (from cffi!=1.11.3,>=1.7->cryptography>=2.2.1->pyopenssl) (2.19)

I saw the AttributeError: 'module' object has no attribute 'SSL_ST_INIT' error too.

Doing

sudo pip install pyOpenSSL==16.2.0

resolved it for me.

In my case, It was throwing the same error for uninstalling and upgrading. I couldn't uninstall or upgrade.

AttributeError: 'module' object has no attribute 'SSL_ST_INIT'


Following worked for me.

# rm -rf /usr/lib/python2.7/site-packages/OpenSSL/

# rm -rf /usr/lib/python2.7/site-packages/pyOpenSSL-16.1.0.dist-info

# rm -rf /usr/lib/python2.7/site-packages/pyOpenSSL-18.0.0-py2.7.egg

# pip2.7 install pyopenssl

Collecting pyopenssl

Downloading 

.

.

100% |████████████████████████████████| 61kB 5.8MB/s 

Collecting cryptography>=2.2.1 (from pyopenssl)

.

.

Installing collected packages: cryptography, pyopenssl

Found existing installation: cryptography 1.7.2

Uninstalling cryptography-1.7.2:

  Successfully uninstalled cryptography-1.7.2

Successfully installed cryptography-2.2.2 pyopenssl-18.0.0

WARNING: Try this only if upgrading(sudo pip install pyOpenSSL==16.2.0) or uninstalling(pip uninstall pyopenssl) doesn't help

Just in case anyone else isn't finding exactly the right incantations to make this work, as of Nov 2018 the thing that worked for me was:


sudo rm -rf /usr/local/lib/python2.7/dist-packages/OpenSSL/
sudo apt install --reinstall python-openssl


Good luck!

I just encountered this on my Ubuntu 16.04 host. There appears to be a version conflict between the apt repo packages for python-openssl and python-crypotgraphy, vs what someone installed manually with pip into /usr/local/python2.7/dist-packages.

Once it got into this state, the system standard pip couldn't execute, either. I got around the chicken-and-egg problem by manually setting a PYTHONPATH environment variable that excluded the /usr/local part of the tree thusly:

    $ export PYTHONPATH="/usr/lib/python2.7:/usr/lib/python2.7/plat-x86_64-linux-gnu:/usr/lib/python2.7/lib-tk:/usr/lib/python2.7/lib-old:/usr/lib/python2.7/lib-dynload:/usr/lib/python2.7/dist-packages:/usr/lib/python2.7/dist-packages/gtk-2.0"

    $ /usr/bin/pip uninstall cryptography

    $ unset PYTHONPATH

I acquired the above list of library directories to use with the python shell:

    import sys

    for p in sys.path:

       print(p)

and then copying everything listed except the one /usr/local directory. Your system may have a different list in its path. Adjust accordingly.

I also had some manual apt-get install --reinstall python-openssl python-cryptography commands scattered in my bash history, which may or may not have been necessary.

export PYTHONPATH="/usr/lib/python2.7:/usr/lib/python2.7/plat-x86_64-linux-gnu:/usr/lib/python2.7/lib-tk:/usr/lib/python2.7/lib-old:/usr/lib/python2.7/lib-dynload:/usr/lib/python2.7/dist-packages:/usr/lib/python2.7/dist-packages/gtk-2.0"
apt-get install --reinstall python-openssl

I had the same issue and as pip wasn't working anymore I had to do his job manually:

wget https://files.pythonhosted.org/packages/40/d0/8efd61531f338a89b4efa48fcf1972d870d2b67a7aea9dcf70783c8464dc/pyOpenSSL-19.0.0.tar.gz

tar -xzvf pyOpenSSL-19.0.0.tar.gz

cd pyOpenSSL-19.0.0

sudo python setup.py install

After that everything worked as expected.