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Check how LUKS password woks. Maybe there are some cache and that's why you need to type (same) password only once.

decrypt_keyctl

decrypt_keyctl

A passphrase caching script to be used in /etc/crypttab on Debian and Ubuntu. When there are multiple cryptsetup (either plain or LUKS) volumes with the same passphrase, it is an unnecessary task to input the passphrase more than once.

Just add this script as keyscript to your /etc/crypttab and it will cache the passphrase of all cryptab entries with the same identifier.

Either copy decrypt_keyctl into the default search path for keyscripts from cryptsetup /lib/cryptdisks/scripts/. So you can just write keyscript=decrypt_keyctl in /etc/crypttab, or use a random path of your choice and give the full path e.g keyscript=/sbin/decrypt_keyctl.