Normally the jail and handcuffs have 100% effectiveness at preventing nightly escapes.
I believe that Emily is a bit unique among NPC characters due to her being implemented earlier than the rest, so her escape event does not consider the possibility of being jailed. Cali's event at least considers whether she is in the jail when her escape event occurs. This is just speculation based on having read the code, but NPC events are not implemented consistently and I haven't gotten around to reworking them.
Viewing post in Jail
Thank you for the clarifications. I will be waiting for the future updates and fixes whenever that is, both in the 1st and 2nd games. Need to finish the 1st game first at least once though, lmao. I have been playing at least more than 20 times already, most of which lasted only a few days in due to role playing complications.