But if you do this, don't you have to enter two passwords each time you wake? One for LUKS, one for the system login?

Well yes and I don't see how this can be avoided.

Do you mean with with current software? How to avoid it in general is straightforward.

If you're the only one with the disk password then the simple answer is make both passwords the same and make the different parts of the system communicate better.

If you want multiple users, give them each a different boot password and encrypt a separate copy of the disk key with each one. That password can be their login password too, or it can encrypt their login.

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