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I'm against the death penalty, but the engineer in me wants to solve this problem.

So why not put the patient to sleep first with anesthetic drugs? After that the mask should not be a bother.

The problem is that anaesthesia has proven difficult for non-medics to reliably administer.

(As demonstrated by this botched execution, which used pentobarbital - a barbituate used for anaesthesia)

Right, then you need a medical professional willing to do it, and that probably gets difficult.