Why Does My 5-Year-Old Wake Up So Often? | Toddler Sleep Expert Q&A

I love when you send me your sleep training questions over on Instagram—it’s one of my favorite ways to connect with you! Every Wednesday, I hop on @awesomelittlesleepers to answer what’s on your mind, so definitely come find me there. But today, I’ve gathered some of the most common questions I get and answered them all right here, just for you. 

Let’s talk through some of the most common—and honestly, most exhausting—sleep struggles families face. If your child keeps waking up in the middle of the night, we’ll cover why that might be happening and what you can do to gently break the cycle. We’ll also get into what to do if your little one is afraid to be alone at night (because clinginess isn’t just about bedtime—it’s often about feeling safe). And finally, if you’re wondering whether health insurance ever covers sleep support, we’ll dig into that too. Let’s get you some answers—and hopefully, a lot more sleep.

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>>Watch this blog on my Awesome Little Sleepers YouTube channel! 👇

My 5-year-old goes to bed independently, but wakes up 1-3 times every night. What gives?

Ugh, the dreaded overnight wake-ups. When it comes to toddler sleep, frankly, these suck. But first of all, great job at bedtime! The top reason most kids wake up overnight is because they get used to falling asleep with mom or dad in the room. But your kiddo is already falling asleep independently at bedtime, without mom or dad.

What reward or benefit could your child be receiving from their overnight wake-ups? 

Could it be that they know they’ll get a hug, a kiss, to sleep in bed with you, or be tucked in again? Kids are real creatures of habit, and they can actually get hooked on these middle-of-the-night interactions with you! Think about your behavior and what might be encouraging wake-ups. Then, break those routines so your kiddo doesn’t keep expecting them in the wee hours of the night. 

My 3-year-old child is scared of being alone, especially at bedtime. Help!

Getting clingy at bedtime is pretty common with toddlers. But if you’ve got a kid who struggles with playing independently or spending any time away from you, I recommend working on daytime independence first. I have a few tips to help you do this:

• Never sneak out. If your kid struggles with being dropped off at daycare or with a babysitter, it seems like a great idea to distract and sneak out. But what happens is it makes your child MORE clingy. They’re worried as soon as they look away, you’ll disappear.

• Prep your kiddo ahead of time. “Okay, mommy’s going to drop you off with your teacher now. You’re going to play with your friends, and I’ll be back to pick you up in a few hours.” Let your child know when you’re leaving, say goodbye (keep it brief), and then leave. 

• Keep your word. When you go back to school to pick them up, remind them that even when you leave, you always come back. They’ll start to internalize that and feel more secure when you’re away. Even a short mantra, like “Mommy always comes back” when you drop off and pick up can be helpful. 

• Catch them being good. Start an engaging activity with them (Legos, a puzzle) and then say, “Mommy’s going to run to the bathroom real quick, I’ll be right back.” Leave for a few minutes (if they can tolerate that long), and when you come back in, remind and reinforce how great they did without you. “Look what you got done with Legos while I was in the bathroom!”

Is your sleep course covered by insurance?

In Canada and Australia, traditional insurance may cover sleep training. But in America, it does not. There’s good news, though! Many HSA or FSA plans will cover the cost of a course like mine, Sleep Tight Without A Fight. The best part of using your HSA or FSA funds is you’re using pre-tax funds. You may need to pre-pay yourself and then submit your receipt to your administrator for reimbursement, so it helps to check your plan for more details. I also have a blog post with more HSA/FSA information that you can check out here. 

Have a toddler sleep question you’d like answered?

Drop me a DM over on Instagram and get the answers! @awesomelittlesleepers