You'd either need to setup something like Cygwin and use openssl with that, refer: https://www.ssl.com/how-to/install-openssl-on-windows-with-cygwin/
or
Install/Setup the Windows Subsystem for Linux (WSL) and install a linux distro like Ubuntu, refer: https://ubuntu.com/wsl
Also, I downloaded the oldest Bitcoin Wallet APK that I could find from the app github (version v3.11). I installed it on the Bluestacks Android Emulator and then created an encrypted "wallet-keys" export file... after mucking around in Ubuntu (in WSL) trying to decrypt this export with "openssl", I found a stackexchange comment that indicated that "old versions of OpenSSL" used a different hash function when generating the encrypt/decrypt key from the user entered passphrase... essentially, they moved from MD5 to SHA-256 by default:
A message digest is used to create the encrypt/decrypt key from a human-entered passphrase. In OpenSSL 1.1.0 we changed from MD5 to SHA-256. We did this as part of an overall change to move away from the now-insecure and broken MD5 algorithm. If you have old files, use the "-md md5" flag to decrypt them.
So, by adding the "-md md5" flag to the command, the decrypt (of "old" files) works:
For reference, here is my "test" data...
Contents of my bitcoin-wallet-keys file:
6R1uHe/ulIjYv5Bkylv4ZtWPYnM5Jl6TMRWX1Q+7cCFBt3BKMdVLNCV8OcGofEs23XhWLT/j/YoH
C+0PfcS21mNjF0u42PVa9BJYBx4JfHSvwx0R3GjubszONRp+XRZZoJnU0Re7BzT+OELp8VLJfobO
HQ1sfwg=
commandline:
Contents of the generated "out" file
L4oyNUNUhDPx5Vd3eShN8Q3fc7MeMxcGQA4WseU8Ys6Ebs7y8FKx 2020-11-17T05:08:03Z
Installed Ubuntu on a VirtualBox and followed your instructions down to the letter. It worked.
Thank you so much HCP - you went above and beyond here. Legend.
Really appreciated.