So by adding "-md md5" on Debian 9 it works on older OpenSSL encoded string: Now, when I input my seemingly good passphrase I get back: Supplying the -md md5 option should solve the issue: $ openssl enc -d -md md5 -in encrypted -out decrypted See also. Warning: Since the password is visible, this form should only be used where security is not important. 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 … I was trying to recover some encrypted backups and it turns out libressl and openssl can't decrypt each other's formats. OpenSSL has probably been updated since you originally encrypted your files so your file may very well have been encrypted using an older version. openssl aes decryption 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 … 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 OpenSSL 1.1.0 changed the default digest algorithm for the dgst and enc commands from MD5 to SHA256. If you have data encrypted with 1.0.2 or older, you have to specify MD5 as the digest algorithm: 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? >You have to represent the hash function as a circuit in CNF. 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. As for your particular problem: OpenSSL changed message digest it uses. The other way around you need '-md sha256' to keep 1.0 happy. You just need to decrypt them with an extra command line argument added -md mda5. See if there is a way. You may need to take the C code for the decryption functions and md5 hashing functions, then compile it to verilog. They changed the default digest from md5 to sha256 to create the key. "bad decrypt" while decrypting. Option -a should also be added while decryption: $ openssl enc -aes-256-cbc -d -a -in file.txt.enc -out file.txt Non Interactive Encrypt & Decrypt. bah. 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