MacOS High Sierra 10.13.6, python3.7 installation

After installing python 3.7 from python.org, running the Install Certificate.command resulted in the below error. Please, can you provide some guidance? Why does Install Certificate.command result in error?

[Some background] Tried to install python via anaconda, brew and python.org, even installing version 3.6.6, hoping I could get one of them to work. Each installation resulted in ssl certification errors when I tried to install a package. See further below for example error from current python 3.7 installation.

I read every page with any reference to openssl errors and followed every instruction. That last one probably has done more damage to my machine tbh. I installed, uninstalled and reinstalled from each of anaconda, brew and python.org, deleting and cleaning a bunch of folders along the way, trying to make a clean installation. Along the way, I even managed to delete pip, wheel and setuptools from site-directories folder of the apple preinstalled python version. So all in all, after a week of python installation hell, I am totally stuck.

 Collecting certifi
  Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/certifi/
  Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/certifi/
  Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/certifi/
  Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/certifi/
  Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/certifi/
  Could not fetch URL https://pypi.org/simple/certifi/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/certifi/ (Caused by SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))) - skipping
  Could not find a version that satisfies the requirement certifi (from versions: )
No matching distribution found for certifi
Traceback (most recent call last):
  File "<stdin>", line 44, in <module>
  File "<stdin>", line 25, in main
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/subprocess.py", line 328, in check_call
    raise CalledProcessError(retcode, cmd)
subprocess.CalledProcessError: Command '['/Library/Frameworks/Python.framework/Versions/3.7/bin/python3.7', '-E', '-s', '-m', 'pip', 'install', '--upgrade', 'certifi']' returned non-zero exit status 1.
logout
Saving session...
...copying shared history...
...saving history...truncating history files...
...completed.

[Process completed]

pip3 install numpy results in the below error

Collecting numpy
  Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/numpy/
  Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/numpy/
  Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/numpy/
  Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/numpy/
  Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/numpy/
  Could not fetch URL https://pypi.org/simple/numpy/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/numpy/ (Caused by SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))) - skipping
  Could not find a version that satisfies the requirement numpy (from versions: )
No matching distribution found for numpy

EDIT post @newbie comment

Based on the most upvoted answer in that post, I tried the following:

$ curl https://bootstrap.pypa.io/get-pip.py -o get-pip.py
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 1604k  100 1604k    0     0   188k      0  0:00:08  0:00:08 --:--:--  148k

$ python3 get-pip.py
Collecting pip
  Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/pip/
  Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/pip/
  Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/pip/
  Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/pip/
  Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /simple/pip/
  Could not fetch URL https://pypi.org/simple/pip/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/pip/ (Caused by SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))) - skipping
  Could not find a version that satisfies the requirement pip (from versions: )
No matching distribution found for pip

$ pip3 search numpy
Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /pypi
Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /pypi
Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /pypi
Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /pypi
Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)'))': /pypi
Exception:
Traceback (most recent call last):
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 600, in urlopen
    chunked=chunked)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 343, in _make_request
    self._validate_conn(conn)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 849, in _validate_conn
    conn.connect()
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connection.py", line 356, in connect
    ssl_context=context)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/util/ssl_.py", line 359, in ssl_wrap_socket
    return context.wrap_socket(sock, server_hostname=server_hostname)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ssl.py", line 412, in wrap_socket
    session=session
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ssl.py", line 850, in _create
    self.do_handshake()
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ssl.py", line 1108, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/requests/adapters.py", line 445, in send
    timeout=timeout
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 667, in urlopen
    **response_kw)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 667, in urlopen
    **response_kw)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 667, in urlopen
    **response_kw)
  [Previous line repeated 1 more times]
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/connectionpool.py", line 638, in urlopen
    _stacktrace=sys.exc_info()[2])
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/urllib3/util/retry.py", line 398, in increment
    raise MaxRetryError(_pool, url, error or ResponseError(cause))
pip._vendor.urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /pypi (Caused by SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)')))

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_internal/basecommand.py", line 141, in main
    status = self.run(options, args)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_internal/commands/search.py", line 48, in run
    pypi_hits = self.search(query, options)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_internal/commands/search.py", line 65, in search
    hits = pypi.search({'name': query, 'summary': query}, 'or')
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/xmlrpc/client.py", line 1112, in __call__
    return self.__send(self.__name, args)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/xmlrpc/client.py", line 1452, in __request
    verbose=self.__verbose
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_internal/download.py", line 788, in request
    headers=headers, stream=True)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/requests/sessions.py", line 559, in post
    return self.request('POST', url, data=data, json=json, **kwargs)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_internal/download.py", line 396, in request
    return super(PipSession, self).request(method, url, *args, **kwargs)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/requests/sessions.py", line 512, in request
    resp = self.send(prep, **send_kwargs)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/requests/sessions.py", line 622, in send
    r = adapter.send(request, **kwargs)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/cachecontrol/adapter.py", line 53, in send
    resp = super(CacheControlAdapter, self).send(request, **kw)
  File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/site-packages/pip/_vendor/requests/adapters.py", line 511, in send
    raise SSLError(e, request=request)
pip._vendor.requests.exceptions.SSLError: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /pypi (Caused by SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1045)')))

=========== EDIT2 : searched for all locations where copies of openssl.cnf file exists. Does this seem right?

$ mdfind openssl.cnf
/usr/local/etc/openssl/openssl.cnf
/opt/vagrant/embedded/ssl/openssl.cnf
/opt/vagrant/embedded/ssl/openssl.cnf.dist
/private/etc/ssl/openssl.cnf
/System/Library/OpenSSL/openssl.cnf
/opt/vagrant/embedded/ssl/misc/CA.pl

wanted to answer my own question as I seem to have fixed most of the issues. The solution:

Created a pip directory and then a pip.conf file in $HOME/Library/Application Support
To the pip.conf added code

[global] trusted-host = pypi.python.org pypi.org files.pythonhosted.org
Started installing using

$ pip install --trusted-host pypi.org --trusted-host files.pythonhosted.org pip
Then tried pip install which worked, so used that to install numpy, pandas, geopy etc.
Successfully ran the Install CertificateCommand file in Applications/Python 3.7

Results: