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It sounds like a sleep association issue, primarily. I would recommend a few different things! There is an Instagram account called Our Mama Village that is amazing. She is a therapist and has a Bedtime Battles course that could help. It would be age appropriate. Another more personalized option would be a sleep psychologist — you should be able to get a referral through your PCP and a lot of the larger hospitals offer services via Telehealth due to the pandemic too. If you’re familiar with sleep association, it’s basically meaning that when your kiddo falls asleep with you in the room, if/when they stir and wake up, they expect you to be in the room. They associate sleep with you. With the way they fell asleep. It’s more complex obviously but it sounds a bit like that! There IS hope — our kiddo had this exact same issue among other things, at the same age! Good luck. I’m sorry this is difficult! I know it’s a long road. But it won’t be forever!

@agold: We went through this with my oldest DS but when the twins were born, we really needed him going down easier in his own bed. I used a hand made sticker chart. Started with 3 nights then added to the chart as time passed. Basically any night he’d stay in his bed after we read, and stayed the entire night, he would earn a sticker. After he filled the chart he’d get a prize. We increased it over time and eventually did away with it completely after a month or so. It worked for us!