For encryption, the more random the passphrase is, the stronger the encryption. For a root password this might not matter as much. But if you have someone trying to brute-force it, then random becomes very valuable indeed. Allow me to refer to the Diceware FAQ: http://world.std.com/%7Ereinhold/dicewarefaq.html#electronic For encryption, introducing the entropy of a die is important because it increases the quality of the encryption. To us, it probably doesn't seem like an issue, but if you are using strong encryption, compromise can be fatal. Imagine you are a financial institution. A large organised crime group wants some info, and they have significant computing power at their disposal. By not using 'true' randomness and using the program, you are basically loosening the screws in the lock. Why compromise?
It's also often just easier to use Diceware.

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