SSLError with Python 3.6.x on macOS Sierra


Have you ran into trouble with SSLErrors after upgrading to Python 3.6 on macOS Sierra?  For me, my first encounter was downloading the bokeh sample data (included here).

I finally got a chance to research exactly what was wrong.  Given that Python 3.5 was working on my machine and 3.6 was working on several linux machines, I thought that it could have been an issue with Python 3.6, unlikely as it may be.  After no bug fix version was released I realized that it must be my configuration.

Searching, I found one result related to this in the Python issue tracker: Issue 28150.  One answerer points out that Python on macOS no longer relies on Apple’s version of OpenSSL, instead it is shipped with a new one.  The gotcha: this new one does not have trust certificates installed.  All this is detailed in the Readme.

The Installer Readme

So, as the Python issue tracker mentioned, there is an entry in the installer readme.  Perhaps I should read these closer…

Certificate verification and OpenSSL

**NEW** This variant of Python 3.6 now includes its own private copy of OpenSSL 1.0.2.  Unlike previous releases, the deprecated Apple-supplied OpenSSL libraries are no longer used.  This also means that the trust certificates in system and user keychains managed by the Keychain Access application and the security command line utility are no longer used as defaults by the Python ssl module.  For 3.6.0, a sample command script is included in /Applications/Python 3.6 to install a curated bundle of default root certificates from the third-party certifi package (  If you choose to use certifi, you should consider subscribing to the project’s email update service to be notified when the certificate bundle is updated.

The bundled pip included with the Python 3.6 installer has its own default certificate store for verifying download connections.

Two Solutions

There are two solutions as mentioned:

  • Install the certifi package.
  • Run the download script provided with the installer – /Applications/Python 3.6/Install Certificates.command.

For myself, I ran the bundled script and everything seems to be functioning fine.  It seems more than a little odd that this was not done on installation.



Posted by Chad Dotson

A small town Computer Scientist / Software Engineer. Chad enjoys writing Python and JavaScript as well as tinkering with his Raspberry Pi and Arduino. When not programming, he enjoys Photography (especially lightning) and Sci-Fi.


Nice catch!

thank you so much!
I spent two days on this problem. First, my access to online database stopped, and after two days searching for this error, you provided the solution
If you ever visit Zurich, I will buy you a beer or two (or anything else)
Best from Switzerland


Chad Dotson

Thanks! I’m glad I could help! This is the best comment I’ve gotten in a while.

Nelson Lim Tyng Xian

Thanks for the solution so much. I really appreciated that. I was struggling to look for the solution, ended up this is the only solution I get, the rest just told me that it is a ssl problem. Thanks again!!

Chad Dotson

No problem, glad you found it useful. It seems to be more obscure than it should be.

Tarun Lalwani

@Chad, If you see Install Certificate.command, it is again nothing but installing certifi package

26 def main():
25 openssl_dir, openssl_cafile = os.path.split(
24 ssl.get_default_verify_paths().openssl_cafile)
22 print(” — pip install –upgrade certifi”)
21 subprocess.check_call([sys.executable,
20 “-E”, “-s”, “-m”, “pip”, “install”, “–upgrade”, “certifi”])

Chad Dotson

I didn’t look into it but yep. he advantage being that the script also updates your root certificates.

Samrat Ghosh

I did try everything but I still getting the same error
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/http/”, line 1239, in request
self._send_request(method, url, body, headers, encode_chunked)
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/http/”, line 1285, in _send_request
self.endheaders(body, encode_chunked=encode_chunked)
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/http/”, line 1234, in endheaders
self._send_output(message_body, encode_chunked=encode_chunked)
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/http/”, line 1026, in _send_output
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/http/”, line 964, in send
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/http/”, line 1400, in connect
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/”, line 401, in wrap_socket
_context=self, _session=session)
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/”, line 808, in __init__
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/”, line 1061, in do_handshake
File “/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/”, line 683, in do_handshake
ssl.SSLError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:749)

Chad Dotson

Did the script or certify installation give you any errors?

I just received a new MacBook Pro, and am trying to get my development environment setup. The exact same code has worked on Linux and Windows 10. I have already installed certifi, and the otherwise mentioned install script does not exist in my install (from MacPorts). I am using Python 3.5. Any ideas? The is being generated as a result of using this library:

File “/opt/local/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/urllib/”, line 484, in _open
‘_open’, req)
File “/opt/local/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/urllib/”, line 444, in _call_chain
result = func(*args)
File “/opt/local/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/urllib/”, line 1297, in https_open
context=self._context, check_hostname=self._check_hostname)
File “/opt/local/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/urllib/”, line 1256, in do_open
raise URLError(err)

Chad Dotson

Does the error have any further message? From the docs, URLError has a reason attribute that should contain more info.

exception urllib.error.URLError

The handlers raise this exception (or derived exceptions) when they run into a problem. It is a subclass of OSError.


The reason for this error. It can be a message string or another exception instance.

Changed in version 3.3: URLError has been made a subclass of OSError instead of IOError.

Ivan Stamenkovic

I was able to run: pip3 install certifi

After installing, I checked and received message:

pip3 install certifi
Requirement already satisfied: certifi in /Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/site-packages

Now my challenge is how to follow the second instruction from the link you provided:

“Reference the installed certificate authority (CA) bundle, you can use the built-in function:
>>> import certifi

>>> certifi.where()

As I installed certifi for Python 3, I modified above as follows:

>>> import certifi

>>> certifi.where()

I then copy all above and paste in terminal, but I get two types of errors as below:

Ivans-MacBook:~ ivanstamenkovic$ >>> import certifi
-bash: syntax error near unexpected token >'
Ivans-MacBook:~ ivanstamenkovic$
Ivans-MacBook:~ ivanstamenkovic$ >>> certifi.where()
-bash: syntax error near unexpected token
Ivans-MacBook:~ ivanstamenkovic$ ‘/usr/local/lib/python3.6/site-packages/certifi/cacert.pem’
-bash: /usr/local/lib/python3.6/site-packages/certifi/cacert.pem: No such file or directory

The location of Python 3 is:

Ivans-MacBook:~ ivanstamenkovic$ which python3

Now, I am going to try the second solution but I can’t find “Install Certificates.command”

FYI:I have confirmed that the following are installed:

Python 3.6.2
Feedparser 5.2.1
Eclipse Juno
Homebrew 1.3.1

I am running Mac OS Sierra 10.12.5

I have followed these instructions and have had no success. Is there an updated fix?

Chad Dotson

Did you install from or using homebrew? You tried the second option, running the Install Certificates.command?

I have installed python3.6 using home-brew and didn’t find the Install Certificates.command under Applications. Please suggest how to fix the ssl issue the installed the python using home-brew.

Ryan Buynicki

Thanks broseph, worked liked a charm!!!!

Anand Prasad

Thanks Chad, Your instructions worked like a charm. It really helped me to solve Oracle Cloud CLI installation on my new Mac OS. Thanks

You rock, Chad. I’ve had this problem in the past, fixed it, but could not remember how to fix it again later.
Maybe StackOverflow folks could use this solution as well. Keep it going.

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