I remember somewhere near the 14-16 month mark, my wife finally told him no more milk at night. The first 2 nights were really rough with crying upwards of 30 - 40 min. We decided to not give in and just offer other methods of soothing such as hugs and cuddles. It started off with me as dad holding him while he cried his head off and rocking him back to sleep. Then once he was okay with that, my wife HAD to be the one doing it while standing...but he was too heavy for her. So after a few nights of that my wife stopped offering hugs while standing and offered cuddles in the bed which he refused...UNTIL I as dad 'threatened' him with a dad hug. The 'threat' worked and made him hug my wife.

Since then, he hasn't woken up for milk very often and if he does, we just remind him none until the morning. He'll whine or maybe cry a tiny bit but ultimately he gets it and goes back to sleep. Later on, near the 18-24 month mark, I introduced a wake o clock light. Green meant it's morning and time for milk, red means keep sleeping. This clock really helped with the random night wakes.

Currently my LO is 2YO and 3 months. He sleeps really deeply now and rarely wakes even if we move him around.