Why does openssl derive IVs from a password? From https://wiki.openssl.org/index.php/Manual:Enc(1):


  When a password is being specified using one of the other options, the IV is generated from this password.


Why does OpenSSL do this? My expectation would be that an unique IV is generated and encoded in the output message every time you invoke OpenSSL. When decrypting, OpenSSL extracts the IV and uses it.

Is there any reason to derive an IV from a password instead? Is that even safe to do? Aren't you using the same IV each time you use the password? What even is the point of using an IV if it's going to be paired to the encryption key?
If you read the manpage you referenced a bit more carfeully, you will find the following lines:


  -nosalt

do not use a salt 

  
  -salt

use salt (randomly generated or provide with -S option) when encrypting (this is the default).



and


  The -salt option should ALWAYS be used if the key is being derived from a password unless you want compatibility with previous versions of OpenSSL and SSLeay.
  
  Without the -salt option it is possible to perform efficient
  dictionary attacks on the password and to attack stream cipher
  encrypted data. The reason for this is that without the salt the same
  password always generates the same encryption key. When the salt is
  being used the first eight bytes of the encrypted data are reserved
  for the salt: it is generated at random when encrypting a file and
  read from the encrypted file when it is decrypted.


Putting this together we learn:


You should use a random salt, which gets used in the key derivation process (calculating the encryption key and the IV from the password)
If you use a salt, the key and the IV and thus the ciphertext won't be deterministic
Using a random salt is the default behaviour of openssl enc


You can easily check this by running

echo foo |openssl enc -aes-128-cbc -out encrypted -nosalt


and

echo foo |openssl enc -aes-128-cbc -out encrypted


In the first case, the output will be 16 bytes long (one block of AES), in the second case it will be longer, because the salt has to be stored.