Hi
New python 3.6.5 install on win10, You need to upgrade to pip 10.0.1 manually for trusted-host to work

PS C:\Users\morten.sensio> pip install --upgrade pip --trusted-host pypi.org --trusted-host files.pythonhosted.org
Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/pip/
Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/pip/
Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/pip/
Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/pip/
Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/pip/
Could not fetch URL https://pypi.python.org/simple/pip/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.python.org', port=443): Max retries exceeded with url: /simple/pip/ (Caused by SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)) - skipping

PS C:\Users\morten.sensio> pip --version
pip 9.0.3 from c:\users\morten.sensio\appdata\local\programs\python\python36-32\lib\site-packages (python 3.6)
PS C:\Users\morten.sensio> python --version
Python 3.6.5

PS C:\tmp> curl "https://files.pythonhosted.org/packages/0f/74/ecd13431bcc456ed390b44c8a6e917c1820365cbebcb6a8974d1cd04ab4/pip-10.0.1-py2.py3-none-any.whl" -o pip-10.0.1-py2.py3-none-any.whl
PS C:\tmp> python -m pip install --no-index pip-10.0.1-py2.py3-none-any.whl
PS C:\tmp> pip --version
pip 10.0.1 from c:\users\morten.sensio\appdata\local\programs\python\python36-32\lib\site-packages\pip (python 3.6)

But still cert fails:

PS C:\tmp> pip install flask
Collecting flask
  Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/flask/
  Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/flask/
  Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:833)'),)': /simple/flask/
:<skipped>

But now it works with --trusted-host:

PS C:\tmp> pip install flask --trusted-host pypi.org --trusted-host files.pythonhosted.org
Collecting flask
  Downloading https://files.pythonhosted.org/packages/7f/e7/08578774ed4536d3242b14dacb4696386634607af824ea997202cd0edb4b/Flask-1.0.2-py2.py3-none-any.whl (91kB)
    100% |████████████████████████████████| 92kB 23.0MB/s
:<skipped>

I believe this is because somone have upgraded the ssl certs recently:

$ openssl s_client -showcerts -servername files.pythonhosted.org -connect files.pythonhosted.org:443 2>/dev/null | openssl x509 -text | grep 'Not Before:'
            Not Before: Jun  1 18:50:10 2018 GMT
^C
$ openssl s_client -showcerts -servername pypi.org -connect pypi.org:443 2>/dev/null | openssl x509 -text | grep 'Not Before:'
            Not Before: Mar 28 00:00:00 2018 GMT
^C

i cannot install or upgrade pip "ssl error" #5448

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