Encryption/decryption doesn’t work well between two different openssl versions

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The default digest was changed from MD5 to SHA256 in Openssl 1.1

Try using -md md5 

cgs@ubuntu:~$ echo "it-works!" > file.txt
cgs@ubuntu:~$ LD_LIBRARY_PATH=~/openssl-1.1.0/ openssl-1.1.0/apps/openssl aes-256-cbc -a -salt -in ~/file.txt -out ~/file.txt.enc -md md5
enter aes-256-cbc encryption password:
Verifying - enter aes-256-cbc encryption password:
cgs@ubuntu:~$ LD_LIBRARY_PATH=~/openssl-1.0.1f/ openssl-1.0.1f/apps/openssl aes-256-cbc -a -in ~/file.txt.enc -d
enter aes-256-cbc decryption password:
it-works!

The ugly details:

The entered password is not used as is by aes (or other encryption) but the command implicitly derives a key from it. The key derivation uses message digest that was changed in openssl 1.1 Use SHA256 not MD5 as default digest.

In case you want to keep it simple password, and not start messing with the keying martial (-K,-iv) just force the same digest with -md

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