I managed to get OpenSSL 3.6.1 on Windows XP.
yt-dlp-XP.zip
openssl.7z (32-bit)
[debug] Command-line config: ['-v']
[debug] User config "C:\Documents and Settings\Nico\Application Data\yt-dlp\config.txt": ['--rm-cache-dir', '--console-title', '--add-metadata', '--embed-thumbnail', '--convert-thumbnails', 'jpg', '--js-runtimes', 'node', '--ppa', 'ffmpeg:-metadata synopsis=""', '-o', '~/Bureaublad/%(title)s.%(ext)s', '-S', 'res:1080,vcodec:avc,acodec:m4a', '--sponsorblock-remove', 'all', '-N', '6']
[debug] Encodings: locale cp1252, fs utf-8, pref cp1252, out cp1252 (No VT), error cp1252 (No VT), screen cp1252 (No VT)
[debug] yt-dlp version local@2026.01.28 [5bf91072b] (win_x86_exe)
[debug] Python 3.11.4 (CPython x86 32bit) - Windows-XP-5.1.2600-SP3 (OpenSSL 3.6.1 27 Jan 2026)
[debug] exe versions: ffmpeg N-122539-g905a432403-WINXP (fdk,setts), ffprobe N-122539-g905a432403-WINXP, phantomjs 1.9.8
[debug] Optional libraries: Cryptodome-3.23.0, brotli-1.2.0, certifi-2026.01.04, mutagen-1.47.0, requests-2.32.5, sqlite3-3.50.4, urllib3-2.6.3, websockets-16.0, yt_dlp_ejs-0.3.2
[debug] JS runtimes: node-20.19.2
[debug] Proxy map: {}
[debug] Request Handlers: urllib, requests, websockets
[debug] Plugin directories: none
[debug] Loaded 1856 extractors
Removing cache dir C:\Documents and Settings\Nico/.cache\yt-dlp ...
Special NodeJS for Windows XP:
Node_XP.7z