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I had to script some of the tasks in my workflow that required checking whether URL is alive or not. Noting it down here for my future reference. I ran into SSL: CERTIFICATE_VERIFY_FAILED error when I tried to access https links on macOS through this tool. I later realize that I didn’t read the README instructions of Python installation properly and missed to run the additional script (/Applications/Python\ 3.6/Install\ Certificates.command) (side effect of always ignoring the readme instructions :blush:). Afer running that script, things worked as expected.