How do you know when your child is ready to leave their toddler bed and move to a bigger bed?
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I upgraded them when I left the nursery. We co-slept till my son was 4 and my daughter was 3. They have twin beds now with the tops touching so they can continue to hold hands. The transition has been harder on me vs them haha 
When they can stay in bed all night not get up run around and get into everything
When they sleep all night and don’t roll all over as much. My son was 5. He used to be a crazy sleeper. 
My daughter was 4. She still sleeps crazy but we built her bed with half frames. She still uses it at 14. 
It really depends on what kind of twin bed you want to put them in, if you’re going to do a railing attachment, how tall your child is, and how crazy of a sleeper they are. My 5 year old is still in a toddler bed but he is special needs. He is short for 5 so can definitely stay in this bed for awhile longer. When we go to a twin, we will likely get a short one or one that does not have a box spring so he can get in and out with ease. I’m less worried about him rolling out of the bed while asleep as I am with him getting in/out when awake- but that’s going to vary based on each child. His older brother was in a twin by 5 and I had no concerns.
As soon as they are night trained
Crib mattress saves regular mattress