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About Bozhidar Bozhanov

Bozhidar Bozhanov
Senior Java developer, one of the top stackoverflow users, fluent with Java and Java technology stacks - Spring, JPA, JavaEE, as well as Android, Scala and any framework you throw at him. creator of Computoser - an algorithmic music composer. Worked on telecom projects, e-government and large-scale online recruitment and navigation platforms.

OpenSSL Key and IV Padding

OpenSSL is an omnipresent tool when it comes to encryption. While in Java we are used to the native Java implementations of cryptographic primitives, most other languages rely on OpenSSL.

Yesterday I was investigating the encryption used by one open source tool written in C, and two things looked strange: they were using a 192 bit key for AES 256, and they were using a 64-bit IV (initialization vector) instead of the required 128 bits (in fact, it was even a 56-bit IV).

But somehow, magically, OpenSSL didn’t complain the way my Java implementation did, and encryption worked. So, I figured, OpenSSL is doing some padding of the key and IV. But what? Is it prepending zeroes, is it appending zeroes, is it doing PKCS padding or ISO/IEC 7816-4 padding, or any of the other alternatives. I had to know if I wanted to make my Java counterpart supply the correct key and IV.

It was straightforward to test with the following commands:

# First generate the ciphertext by encrypting input.dat which contains "testtesttesttesttesttest"
$ openssl enc -aes-256-cbc -nosalt -e -a -A -in input.dat -K '7c07f68ea8494b2f8b9fea297119350d78708afa69c1c76' -iv 'FEDCBA987654321' -out input-test.enc
# Then test decryption with the same key and IV
$ openssl enc -aes-256-cbc -nosalt -d -a -A -in input-test.enc -K '7c07f68ea8494b2f8b9fea297119350d78708afa69c1c76' -iv 'FEDCBA987654321'
# Then test decryption with different paddings
$ openssl enc -aes-256-cbc -nosalt -d -a -A -in input-test.enc -K '7c07f68ea8494b2f8b9fea297119350d78708afa69c1c76' -iv 'FEDCBA9876543210'
$ openssl enc -aes-256-cbc -nosalt -d -a -A -in input-test.enc -K '7c07f68ea8494b2f8b9fea297119350d78708afa69c1c760' -iv 'FEDCBA987654321'
$ openssl enc -aes-256-cbc -nosalt -d -a -A -in input-test.enc -K '7c07f68ea8494b2f8b9fea297119350d78708afa69c1c76000' -iv 'FEDCBA987654321'
$ openssl enc -aes-256-cbc -nosalt -d -a -A -in input-test.enc -K '07c07f68ea8494b2f8b9fea297119350d78708afa69c1c76' -iv 'FEDCBA987654321'
bad decrypt

So, OpenSSL is padding keys and IVs with zeroes until they meet the expected size. Note that if -aes-192-cbc is used instead of -aes-256-cbc, decryption will fail, because OpenSSL will pad it with fewer zeroes and so the key will be different.

Not an unexpected behavaior, but I’d prefer it to report incorrect key sizes rather than “do magic”, especially when it’s not easy to find exactly what magic it’s doing. I couldn’t find it documented, and the comments to this SO question hint in the same direction. In fact, for plaintext padding, OpenSSL uses PKCS padding (which is documented), so it’s extra confusing that it’s using zero-padding here.

In any case, follow the advice from the stackoverflow answer and don’t rely on this padding – always provide the key and IV in the right size.

Published on Java Code Geeks with permission by Bozhidar Bozhanov, partner at our JCG program. See the original article here: OpenSSL Key and IV Padding

Opinions expressed by Java Code Geeks contributors are their own.

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