Having key off-machine mitigates a lot of that.
> Unless the junkie who stole your server has an unpatched debian login bug,
the key for disk decryption is in memory at that point. There are methods to take it out of it
E.g. systemd measures basically everything that is part of the boot process (kernel, kernel cli, initrd, ...[1]) into different PCRs, so if any of those are different they result in differen PCR values and won't unlock the boot device (depending on which PCRs you decided to encrypt against). I forgot what excatly it measures, but I remember that some PCRs also get measured during the switch_root operation from initrd -> rootfs which can be used to make something only unlock in the initrd.
If this fails you can always manually input the decryption key and reregister with the TPM. The whole point of this setup is you can't just use a bootable USB to reset the devices password.
You'll be dropped into "enter disk crypt password please" prompt.