We've had these challenges too. Although it is every sleep for my little miss.

What I would do in your case. Keep your routine and keep persisting, eventually he'll get it. Additionally I would put him down in the usual manner, then if he doesn't settle I would comfort him. For us holding DD until she is 3/4 gone helps. Then I put her down on her side and pat her bottom until she falls to sleep. If she wakes again I'll repeat the process or offer boob. hth