Files encrypted with openssl aes-256 (from command line) with macOS Monterey cannot be decrypted with openssl in macOS Ventura

I had the same problem. File encrypted pre-Ventura cannot be decrypted in Ventura, and file encrypted in Ventura cannot be decrypted pre-Ventura.

Luckily I had an old laptop that could not be upgraded to Ventura, so I used that to decrypt my files

I'm using "openssl enc -aes-256-cbc -salt" to encrypt and "openssl enc -d -aes-256-cbc" to decrypt.

So glad to find these examples... I had same issue with not being able to use openssl to decrypt my file after upgrading from Monterey to Ventura.

Luckily, we have access to a MBP running Monterey, moved the file there, decrypted there to cleartext just fine with no problem.

We then moved the cleartext file back to Ventura, and now we are able to encrypt/decrypt that file in Ventura with the old command without any problems.

See if this helps: https://unix.stackexchange.com/questions/606493/cannot-decrypt-files-on-a-mac-using-openssl

openssl enc -aes-256-cbc -d -md md5 -in file