My home server runs OpenBSD 5.3 with Samba serving files to several Windows machines. I wrote a script to backup video files by encrypting each file with
openssl enc -aes-256-cbc and uploading it to Amazon S3. To test one possible restore scenario, I tried running the script on a file, downloading the file to one of the Windows machines, and decrypting it using several programs advertised as decrypting AES-encrypted files, but they weren't able to decrypt it. Can a file encrypted by OpenSSL be decrypted only by OpenSSL? Can a file encrypted by OpenSSL on OpenBSD be decrypted only by OpenSSL on OpenBSD?
For the record, I had no problem downloading the file to my server and decrypting it using OpenSSL. However, I'm interested in knowing if my videos on S3 (quickly archived to Glacier) can remain accessible regardless of my choice of server setup.