Hello Reino (OT, but I'm really missing your Vista-compatible FFmpeg compiles )
While your OpenSSL binaries (archive "openssl-3.5.2-win32-shared-xpmod-sse.7z") may very well be XP+ compatible , they don't work out-of-the box as CPython dependency by swapping the already existing DLLs (of openssl v3.1.0-dev) inside cmalex's CPython assemblies with them; he's been using the same (quite deprecated and now rather insecure ) v3.1.0-dev DLLs in his 3.8.13, 3.9.13, 3.10.8 and 3.11.4 CPython offerings, but the thing is the libcrypto-3.dll and libssl-3.dll inside CPython work in conjunction with two Python DLLs, files "_ssl.pyd" and (possibly) "_hashlib.pyd"; the existing .pyd files are incompatible with your own openssl DLLs ...
BTW, I'm on Vista SP2 32-bit, so I'm using cmalex's Vista-compatible 3.11.4 assembly; with the original v3.1.0-dev DLLs:
python
Python 3.11.4 (heads/My3.11.4-dirty:1c368b1ab42, Aug 24 2025, 19:29:33) [MSC v.1900 32 bit (Intel)] on win32
Type "help", "copyright", "credits" or "license" for more information.
>>> import ssl
>>> ssl.OPENSSL_VERSION
'OpenSSL 3.1.0-dev '
>>> ^Z
<redacted>\3.11.4\cmalex\Python3114-32_Vista>
Overwrite them with your own v3.5.2 DLLs and...
python
Python 3.11.4 (heads/My3.11.4-dirty:1c368b1ab42, Aug 24 2025, 19:29:33) [MSC v.1900 32 bit (Intel)] on win32
Type "help", "copyright", "credits" or "license" for more information.
>>> import ssl
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File "<redacted>\3.11.4\cmalex\Python3114-32_Vista>\Lib\ssl.py", line 100, in <module>
import _ssl # if we can't import it, let the error propagate
^^^^^^^^^^^
ImportError: DLL load failed while importing _ssl: The specified procedure could not be found.
>>> ssl.OPENSSL_VERSION
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
NameError: name 'ssl' is not defined
>>> ^Z
<redacted>\3.11.4\cmalex\Python3114-32_Vista>
I guess newer versions of "_ssl.pyd" and "_hashlib.pyd" must be provided for openssl-3.5.2 compatibility ...
@nicolaasjan
openssl-3.1.0-dev inside cmalex's assemblies (both 3.10.18 and 3.11.4, both XP/Vista variants) can be updated to a slightly more recent version, openssl-3.1.2, by using the OpenSSL-3.1.2 DLLs cmalex had compiled in the past for another of his projects, ProxyMII; link below:
https://mega.nz/folder/68dj2YTY#As2w31IO4Smr7gy6p1ciSg/file/Pl9yzapZ
Proof:
python
Python 3.11.4 (heads/My3.11.4-dirty:1c368b1ab42, Aug 24 2025, 19:29:33) [MSC v.1900 32 bit (Intel)] on win32
Type "help", "copyright", "credits" or "license" for more information.
>>> import ssl
>>> ssl.OPENSSL_VERSION
'OpenSSL 3.1.2 1 Aug 2023'
>>> ^Z
<redacted>\3.11.4\cmalex\Python3114-32_Vista>
NB: When using the Vista variants of py3.10.18/3.11.4 to compile yt-dlp_x86.exe for Vista, none of the wrapper DLLs (kernelxp.dll, ntext.dll, psapi.dll) are needed; because your resultant yt-dlp.exe binaries (for Vista) still contain file "psapi.dll", redundant on Vista ; come to think of it, I don't think file "ws2_xx.dll" is needed on Vista either, but I'm not dead certain; only cmalex can vouch for that ...
Many thanks and praise to both cmalex and nicolaasjan for... keeping the torch lit (i.e. yt-dlp accessible on Win<8.1) ...