By default a user is prompted to enter the password. You may need to take the C code for the decryption functions and md5 hashing functions, then compile it to verilog. Everything works flawlessly if you provide the old digest (which was MD5 and now is SHA256): openssl aes-256-cbc -d -md MD5 -salt -pass KEY -in FILE -out FILE.OUT Offline Supplying the -md md5 option should solve the issue: $ openssl enc -d -md md5 -in encrypted -out decrypted See also. If I encrypt a file on 11.1 using aes256: master# openssl enc -aes256 -in xxx.c -out xxx.enc Then transfer xxx.enc to 12.0 and try to decrypt it, I get garbage with a couple of what appear to be warnings: test# openssl enc -d -aes256 -in xxx.enc enter aes-256-cbc decryption password: *** WARNING : deprecated key derivation used. So by adding "-md md5" on Debian 9 it works on older OpenSSL encoded string: OpenSSL 1.0.2 still used MD5 and 1.1.0 switched to SHA256. digital envelope routines:EVP_DecryptFinal_ex:bad decrypt: Don’t panic just yet! I was trying to recover some encrypted backups and it turns out libressl and openssl can't decrypt each other's formats. bah. "bad decrypt" while decrypting. Based on John's hint of the usage of md5, I did openssl enc -aes-256-cbc -d -md md5 -in file, and it was able to correctly decrypt the contents (although it still produces the … OpenSSL 1.1.0 changed the default digest algorithm for the dgst and enc commands from MD5 to SHA256. Enter pass phrase for ./id_rsa: unable to load Private Key 140256774473360:error:06065064:digital envelope routines:EVP_DecryptFinal_ex:bad decrypt:evp_enc.c:544: 140256774473360:error:0906A065:PEM routines:PEM_do_header:bad decrypt:pem_lib.c:483 "bad decrypt" is pretty clear. OpenSSL has probably been updated since you originally encrypted your files so your file may very well have been encrypted using an older version. You just need to decrypt them with an extra command line argument added -md mda5. You're not entering the correct passphrase for your private key. Now, when I input my seemingly good passphrase I get back: bad decrypt 140150542661448:error:0606506D:digital envelope routines:EVP_DecryptFinal_ex:wrong final block length:evp_enc.c:589: Why does decryption fail with overly long keys? JSYK, since you posted (even an encrypted form of) your private key to a public list, you should treat it as compromised, generate a new keypair, and rekey your CA.-Kyle H On Tue, Dec 16, 2008 … >You have to represent the hash function as a circuit in CNF. If you have data encrypted with 1.0.2 or older, you have to specify MD5 as the digest algorithm: The other way around you need '-md sha256' to keep 1.0 happy. 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