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We transitioned DD1 at 2 years, 5 months.

After sleeping through the night consistently for 7 months, her sleep randomly became horrible. She was waking up at least 4 times a night, and eventually would just refuse to sleep in her crib and ask to sleep on the couch. EVERY SINGLE NIGHT. It was so weird! My mom suggested that maybe she liked sleeping on the couch because she felt too confined in her crib, and that maybe she was bumping up against the crib slats in her sleep.

So at 29 months, we decided to set up a twin bed for her to see how she did. We were so tired, we were willing to try anything. We took her to ikea and let her pick out a new comforter, and then got her flannel sheets and a comfy pillow. (None of those thing she had in her crib, so it was all very new to her!)

The first night, she woke up once and called for us, and we just went and laid next to her and she went right back down. Then she STTN every single night since then (this was back in October). so I guess my mom was right....she probably was uncomfortable in her crib and needed more space. Her sleep has never been better, and I almost wish we transitioned her sooner!

Another nice part about putting her in a twin is that there is room to lay down with her and read books, or to lay with her and comfort her on the nights she's sick and not sleeping well.

Good luck!

We transitioned at 2. We left his crib set up and just tried to get him to sleep in the big boy bed. He would beg to get in the crib and try to climb up the side but it only took a few nights until he adjusted.