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See transcript below. I am running MacOS 10.14.6. Thanks, Chris
% youtube-dl -U --verbose
[debug] System config: []
[debug] User config: []
[debug] Custom config: []
[debug] Command-line args: [u'-U', u'--verbose']
[debug] Encodings: locale UTF-8, fs utf-8, out UTF-8, pref UTF-8
[debug] youtube-dl version 2020.03.24
[debug] Python version 2.7.16 (CPython) - Darwin-18.7.0-x86_64-i386-64bit
[debug] exe versions: ffmpeg 3.3.2, ffprobe 3.3.2
[debug] Proxy map: {}
Traceback (most recent call last):
File "/usr/local/bin/youtube-dl/youtube_dl/update.py", line 46, in update_self
newversion = opener.open(VERSION_URL).read().decode('utf-8').strip()
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 429, in open
response = self._open(req, data)
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 447, in _open
'_open', req)
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 407, in _call_chain
result = func(*args)
File "/usr/local/bin/youtube-dl/youtube_dl/utils.py", line 2728, in https_open
req, **kwargs)
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 1198, in do_open
raise URLError(err)
URLError: <urlopen error [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)>
ERROR: can't find the current version. Please try again later.