Does cryptsetup support building with libressl? Ebuild sys-fs/cryptsetup-1.7.5::gentoo provides only next options exactly-one-of ( gcrypt kernel nettle openssl )
Read ebuild: CRYPTO_BACKENDS="+gcrypt kernel nettle openssl" IUSE="${CRYPTO_BACKENDS} libressl ..." ^^^^^^^^ REQUIRED_USE="^^ ( ${CRYPTO_BACKENDS//+/} ) ..." LIB_DEPEND="... openssl? ( !libressl? ( dev-libs/openssl:0=[static-libs(+)] ) libressl? ( dev-libs/libressl:=[static-libs(+)] ) ) ..." So to use LibreSSL, you must disable "gcrypt" USE flag and enable "openssl" and "libressl" USE flags.
OK Looks like libressl is a drop-in replacement for openssl in this case.