@VistaLover
I will reply here instead of going offtopic on GitHub in this thread.
You asked:
I used adang1345's CPython 3.14.2 and these dll's. But the dll's from your other link also failed. I also have the 2015-2022 redistributable.
The issue is in the name of these files. E.g. libssl-3-x64.dll instead of libssl-3.dll, as CPython x64 expects.
And, as you have seen, there are no issues at all building the 32bit counterpart using adang's Python with the dll's from your sources.
I have absolutely no idea how to build a Windows 7 compatible Python 64bit and link it against OpenSSL-3.6.0. 😕
Maybe I should ask adang to include a more recent OpenSSL. Preferably the 3.5.4 LTS release.
I did manage to build them on Linux though (with a lot of help from AI 😐).
And then force yt-dlp to use it via an alias: alias yt-dlp='python3.14 /usr/local/bin/yt-dlp' (in the file `.bash_aliases`).
Result:
[debug] Python 3.14.2 (CPython x86_64 64bit) - Linux-5.15.0-164-generic-x86_64-with-glibc2.35 (OpenSSL 3.6.0 1 Oct 2025, glibc 2.35)
(my system itself has the old Python 3.10.12 and OpenSSL 3.0.2)
The challenge was, to install the updated ones in a way that they would not interfere with the system installed ones. It would cause major breakage.