Encrypting and Decrypting Text with OpenSSL
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Last week at work, we had a hackathon, in which the recommendation was to give our (production) Hackathon API a go. This required logging in via a GitHub.com account to retrieve a JSON Web Token to use to authenticate yourself to the API.
I have a general policy of trying to keep my personal and work lives generally unentwined, so did not want to do it on my work machine. Instead, I logged in using my personal machine, but then had to send the JWT to my work email, which I didn't want to do in cleartext, because JWTs are sensitive.
To encrypt it, there are fortunately quite a few options, but in my case, it was a throwaway piece of work, so I thought just encrypting it with a shared secret would be enough, instead of i.e. worrying about GPG/PGP keys.
Although encrypting it worked pretty easily, I found it surprisingly difficult to decrypt on my work Mac and kept getting an error similar to the following:
bad decrypt 130692476720256:error:06065064:digital envelope routines:EVP_DecryptFinal_ex:bad decrypt:../crypto/evp/evp_enc.c:570:
After a while of searching online, I found that this is due to the differences in OpenSSL implementations and how they use message digests, and the solution is to make sure you explicitly use a message digest.
This gives us the following command to encrypt:
openssl enc -aes-256-cbc -pbkdf2 -salt -in file.txt -out file.enc -md sha512 # or to Base64 encode it, so it's safe to go in i.e. the body of an email openssl enc -aes-256-cbc -pbkdf2 -salt -in file.txt -out file.enc -md sha512 -base64
And the following to decrypt:
openssl enc -d -aes-256-cbc -pbkdf2 -md sha512 < file.enc # or if Base64-encoded openssl enc -d -aes-256-cbc -pbkdf2 -md sha512 -base64 < file.enc
Note that if you're on MacOS, with a LibreSSL version ~2.7, you may find that you need to remove the
-pbkdf2 argument for this to work.