First, don't encrypt things directly with OpenSSL.

Second, they're using unauthenticated AES-CBC, so an attacker that knows what file format they're sending can flip bits to exploit bugs and pop calc.exe on them.

Third, reprising the first problem: using OpenSSL to encrypt means you're using OpenSSL's weak password KDF. In fact, I think the defaults when they were using this were single-iteration hash KDF; essentially: salted hashes.

This is like the one application where GPG actually still makes sense to use, and GPG is easier to use here than OpenSSL in addition to being safer.

OBVIOUSLY NONE OF THIS MATTERS. My issue with the article isn't "it recommends weak crypto". My issue is that despite the title, it isn't actually about crypto or surveillance or anything like that.

The article does this:

    > openssl aes-256-cbc -a -salt -in for-you.mp3 -out for-you.mp3.enc

Here's the KDF for that (in PHP):

    $round1 = hex2bin(md5($pwd . $salt));
    $round2 = hex2bin(md5($round1 . $pwd . $salt));
    $round3 = hex2bin(md5($round2 . $pwd . $salt));
    $key = $round1 . $round2;
    $iv = $round3;

It still defaults to that (I'm on Ubuntu 16.04):

    $ openssl version
    OpenSSL 1.0.2g  1 Mar 2016

Ow.

It's just a poetic title - Love in the Time of Cholera isn't about epidemiology either.