"ERROR: can't find the current version. Please try again later." (Mac)

[LiquidLightning]

• [ X ] I've verified that I'm running youtube-dl version 2019.07.16
• [ X ] I've searched the bugtracker for similar bug reports including closed ones
• [ X ] I've read bugs section in FAQ

Failure Log

$ sudo youtube-dl -U -v
[debug] System config: []
[debug] User config: [u'--ffmpeg-location', u'/usr/local/bin/ffmpeg', u'--audio-quality', u'0', u'-i', u'-w', u'--merge-output-format', u'mkv', u'--no-part', u'--username', u'PRIVATE', u'--password', u'PRIVATE']
[debug] Custom config: []
[debug] Command-line args: [u'-U', u'-v']
[debug] Encodings: locale UTF-8, fs utf-8, out UTF-8, pref UTF-8
[debug] youtube-dl version 2019.07.16
[debug] Python version 2.7.10 (CPython) - Darwin-15.6.0-x86_64-i386-64bit
[debug] exe versions: ffmpeg N-93875-gc2771bbf81-tessus
[debug] Proxy map: {}
Traceback (most recent call last):
  File "/usr/local/bin/youtube-dl/youtube_dl/update.py", line 45, 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 431, in open
    response = self._open(req, data)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 449, in _open
    '_open', req)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 409, in _call_chain
    result = func(*args)
  File "/usr/local/bin/youtube-dl/youtube_dl/utils.py", line 2724, in https_open
    req, **kwargs)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/urllib2.py", line 1197, in do_open
    raise URLError(err)
URLError: <urlopen error EOF occurred in violation of protocol (_ssl.c:590)>

ERROR: can't find the current version. Please try again later.
$

Problem

youtube-dl -U does not work under Mac OS X, including OS X El Capitan 10.11.6.

Cause

Python 2.7.10 comes with an outdated version of OpenSSL:

$ python -c 'import ssl; print(ssl.OPENSSL_VERSION)'
OpenSSL 0.9.8zh 14 Jan 2016
$

Workaround

Update manually using instructions at https://ytdl-org.github.io/youtube-dl/download.html:

sudo curl -L https://yt-dl.org/downloads/latest/youtube-dl -o /usr/local/bin/youtube-dl

sudo chmod a+rx /usr/local/bin/youtube-dl

Solution

Update the current version of Python 2. (Do not install a new version such as Python 3 to try to solve this.)

If you are using Homebrew, see here. Issue #15474.

If you are not using Homebrew, download and install the current version of Python 2 -- not Python 3 or newer.

Before installing Python from its .pkg package installer file, you can optionally verify the signature of the .pkg file according to the instructions on the Python download web page.

The Python 2 .pkg installs a Python 2.x folder in the /Applications folder. After Python is installed, run (by double-clicking) the files Update Shell Profile.command and Install Certificates.command located in that Python installation folder.

Success Example Log

Python's version of OpenSSL gets updated:

$ python -c 'import ssl; print(ssl.OPENSSL_VERSION)'
OpenSSL 1.0.2q  20 Nov 2018
$

youtube-dl -U works hereafter:

$ sudo youtube-dl -U -v
[debug] System config: []
[debug] User config: [u'--ffmpeg-location', u'/usr/local/bin/ffmpeg', u'--audio-quality', u'0', u'-i', u'-w', u'--merge-output-format', u'mkv', u'--no-part', u'--username', u'PRIVATE', u'--password', u'PRIVATE']
[debug] Custom config: []
[debug] Command-line args: [u'-U', u'-v']
[debug] Encodings: locale UTF-8, fs utf-8, out UTF-8, pref UTF-8
[debug] youtube-dl version 2019.07.16
[debug] Python version 2.7.16 (CPython) - Darwin-15.6.0-x86_64-i386-64bit
[debug] exe versions: ffmpeg N-93875-gc2771bbf81-tessus
[debug] Proxy map: {}
youtube-dl is up-to-date (2019.07.16)
$