Credited to pip.pypa.io:
Starting with v1.3, pip provides SSL certificate verification over
HTTP, to prevent man-in-the-middle attacks against PyPI downloads.
This does not use the system certificate store but instead uses a
bundled CA certificate store. The default bundled CA certificate store
certificate store may be overridden by using --cert option or by using
PIP_CERT, REQUESTS_CA_BUNDLE, or CURL_CA_BUNDLE environment variables.
In regards to the SSL issue, it depends whether you insist on SSL enforcement, if not, you may use an existing flag to ignore this by appending --trusted-host <server_name> ,in the example below: --trusted-host artifactory.
Some suggestions raised to overcome this issue are suggested here as well: pip install fails with "connection error: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:598)"
Do note, prior to using artifactory as a caching/proxy server for Pypi packages, you should configure the pip.conf and .pypirc files according to the SetMeUp instructions: https://www.jfrog.com/confluence/display/JFROG/PyPI+Repositories#PyPIRepositories-ResolvingfromArtifactoryUsingpip
For example:
pip.conf:
[global]
index-url = http://artifactory:8081/artifactory/api/pypi/pypi-virtual/simple
.pypirc:
[distutils]
index-servers =
virtual
local
remote
devpi
[virtual]
repository: http://artifactory:8081/artifactory/api/pypi/pypi-virtual
username: admin
password: ***
[local]
repository: http://artifactory:8081/artifactory/api/pypi/pypi-local
username: admin
password: ***
[remote]
repository: http://artifactory:8081/artifactory/api/pypi/pypi-org-remote
username: admin
password: ***
[devpi]
repository: http://localhost:3141/admin/dev
username: admin
password: ***