Do you have a usrmerge setup? What does `readlink -f /lib/cryptsetup/askpass` return?
I noticed a problem with usrmerge setups earlier today. The following commit fixes the issue AFAICT: https://salsa.debian.org/cryptsetup-team/cryptsetup/commit/f1c56c19fea6dc988c1f29fb8a510c05286c2900 -- Guilhem.
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