Sleep training is one of the most searched, most googled, most desperately needed topics in early parenthood – and also one of the most misunderstood. It’s not a one-size-fits-all process. It’s not linear. And it is genuinely hard, even when you’re doing everything right.
At Sleep Shore, sleep training is our specialty. And even we had to get certified to do this well. So if you’re in the tick of it right now feeling like it’s not working, take a breath. You’re not failing. You’re just in it.
Here are the 8 most common sleep training challenges we see and exactly how to get through them.
8 Common Sleep Training Challenges (and How to Actually Get Through Them)
Sleep training is so rewarding, but it’s a journey. There are many sleep training methods, challenges, and mistakes that are easy to make as parents. Sleep training isn’t one-size-fits-all, but I’m sharing tips to get through some of the most common sleep training challenges.
1. Sleep Regressions Hit and Everything Falls Apart
Sleep regressions are the plot twist nobody prepared you for. You’re finally in a groove — and then your baby turns 4 months old and the whole thing unravels overnight.
Here’s what’s actually happening: regressions aren’t your baby going backward. They’re your baby’s brain going forward developing, growing, processing new skills. The 4-month regression is actually a permanent shift in how your baby’s sleep cycles work. The 8-month, 12-month, 18-month, and toddler regressions that follow are all tied to developmental leaps too.
They typically last 2-6 weeks. They are temporary. Stay consistent with your method and you will come out the other side.
2. Self-Soothing Feels Like an Impossible Ask
Independent sleep is the holy grail of sleep training and it’s also the hardest skill to teach, because it requires your baby to do something they’ve never had to do before.
Self-soothing isn’t stubbornness. It isn’t manipulation. It’s a skill that has to be learned and like every skill, it takes time and repetition before it clicks. Once it does though? It is genuinely life-changing. For them and for you.
Whatever method you’ve chosen, stick with it. Inconsistency is the single biggest thing that slows this process down. A white noise machine running consistently in the background makes a significant difference during this stage.
3. Bedtime Is Better But Naps Are Still a Disaster
This is one of the most common things I hear: bedtime is finally going okay but naps are still chaos. You are not alone in this.
Naps operate on different biological rhythms than nighttime sleep and they require their own strategy especially during nap transitions, which are some of the most disruptive periods in the entire first three years. The 3-to-2 transition, the 2-to-1 transition, and the eventual drop to no nap are all significant schedule shifts that take time to stabilize.
The key with naps: get the timing right, protect the wake windows, and stay consistent with your pre-nap routine. If you’re struggling with nap math, a schedule notepad can be a game-changer for tracking patterns until the schedule stabilizes.
4. The Timing Feels Completely Off
Early wake-ups at 5am. A toddler who can’t fall asleep until 10pm. A baby who seems tired but fights sleep for an hour. These are timing issues — and they’re incredibly common, incredibly draining, and incredibly fixable once you understand wake windows.
Wake windows are the foundation of sleep timing. Too short and your baby isn’t tired enough to sleep well. Too long and they’re overtired — and an overtired baby is significantly harder to settle than a tired one. Learning your baby’s age appropriate wake windows and working with their natural biological clock rather than against it changes everything.
5. Your Baby Got Sick and You Feel Like You’re Starting Over
Illness is the uninvited guest that shows up right when sleep was finally getting better. And the feeling of watching two weeks of progress disappear in 48 hours is genuinely demoralizing.
Here’s the truth though: the progress isn’t actually gone. The skills your baby has been building are still there. Illness requires you to meet your baby where they are — more comfort, more flexibility, more presence. And that is completely okay and completely appropriate.
When they’re healthy again, give it 2-3 days to resettle and then return to your method. The reset is almost always faster the second time around.
6. Your Baby is Either Wired or Completely Overtired
There’s a narrow window between undertired and overtired — and landing in it consistently is genuinely one of the hardest parts of early sleep training. Miss the window on one side and your baby isn’t ready to sleep. Miss it on the other and the cortisol response kicks in, making it significantly harder for them to settle.
Signs of overtiredness: hyperactivity right before bed, false starts shortly after falling asleep, frequent overnight wakings, and early morning rising. Signs of undertiredness: taking forever to fall asleep, resisting naps, short sleep stretches.
Wake window charts by age are your best friend here. They take the guesswork out of timing and give you a consistent framework to work from.
7. You’re Struggling to Stay Consistent
Let’s be honest about this one: consistency is the hardest part of sleep training for parents — not babies. Because consistency means holding the line on the hard nights. The nights when you’re exhausted and it would be so much easier to just go in, just rock them one more time, just do the thing that gets everyone back to sleep fastest.
Every time you break the method out of exhaustion or desperation, you’re not just taking a step back — you’re teaching your baby that if they escalate long enough, the old thing comes back. That makes the next night harder, not easier.
The nights that feel impossible are the nights that matter most. This is where progress actually happens.
8. Life Gets in the Way
A big move. A new sibling. Travel. The holidays. Starting daycare. Life does not pause for sleep training — and major disruptions can genuinely derail even the most established sleep routine.
Timing matters here. If something significant is on the horizon, it’s worth considering whether now is the right moment to start — or whether waiting a few weeks for things to stabilize will set you up for more consistent success. If you’ve already started and life interrupts, treat it like illness: meet your baby where they are, stay as consistent as you can, and re-establish the routine once the dust settles.
Making It All a Little Easier: The Foundations That Help with Every Challenge
Sleep training challenges are inevitable to some extent- one way or another, your child will find a way to make it feel difficult (toddler moms especially, you know what I mean!). There are, however, some tips to make bedtime feel MUCH easier. These steps can make sleep training less challenging and hopefully reduce the bedtime resistance you may be experiencing.
A consistent bedtime routine
Studies shows that predictable bedtime routines are SO beneficial to children. Predictable bedtime routines improve sleep onset, reduce bedtime resistance, and help children feel safe and regulated. Bath, pajamas, feeding, books, bed; in the same order, every single night. Predictability is the foundation everything else is built on.
Screens off at least 30-45 minutes before bed
Screentime messes with our circadian rhythms big time. Blue light suppresses melatonin production and directly interferes with your child’s ability to feel sleepy at bedtime. This one simple change removes a significant obstacle for a lot of families.
An optimized sleep environment
This is so key! We all feel better when our sleep environment is peaceful- our kids are no different. Make sure the room is dark, set to a temperature of 68-72 degrees Fahrenheit, and quiet with white noise in the background. There are so many baby sleep products and toddler sleep products that are conducive to solid sleep!
A reward system for toddlers
At the end of the day, your toddler wants to be told that they’re doing an amazing job! It can be exciting for them to keep track of bedtimes that go well. If you’re struggling with sleep training challenges, a sleep routine chart with rules that can be checked off can be super beneficial for toddlers. Click here to download my sleep routine chart and sleep rules– these are a game-changer for toddlers!
Sleep training is not about perfection. It is not linear. There will be regressions and illnesses and disruptions and nights where everything falls apart and you wonder if any of it is actually working.
It is. Even on the hard nights, especially on the hard nights, it is working.
Consistency and patience are the two most powerful tools you have. And on the days when both of those feel impossible, remember why you started: because a well-rested baby and a well-rested parent both deserve better than survival mode.
You’ve got this.
Sleep Shore Sleep Consulting
There are so many ways you can sleep train your little one! At the end of the day, each child is different and has unique sleep needs. Sleep training looks different for Stop guessing your way through naps and nights. The problem isn’t that your child can’t sleep – it’s that your current methods and cycles are teaching them the wrong skills. You’ve tried everything to help your little on self-soothe, and you’re exhausted from the constant wake-ups and struggle. YOU deserve more! Waiting from them to “grow out of it” is costing your entire family months of crucial rest.
We don’t just give you a tip; we provide personalized, age-appropriate solutions for newborns, infants, and toddlers that teach the core, life-long skill of independent sleep. STOP losing sleep over a problem we can solve in days.
Sleep Shore offers expert 1:1 support (including in-home services in Boston, Central Michigan, and Northern Michigan). Our calendar is filling fast – we are only accepting a limited number of new clients every month. Don’t wait another week. Click here to schedule your consultation and secure your family’s rest!
See what this mama had to say about our sleep services below:
“We reached out to Molly when our 3.5-year-old was going through all the big changes at once — new room, big boy bed, and becoming a big brother. Bedtime had totally fallen apart and he was sleeping on our floor every single night. We were exhausted and honestly didn’t know how to reset things without making it worse, while also dealing with a newborn!
Molly was exactly what we needed. She gave us a clear plan, but she also made it feel doable. She helped us make the transition fun and exciting for our son, while giving us the confidence to set and hold loving boundaries (which we really needed). It felt supportive, not rigid.
Within one week he was sleeping through the night in his own bed.
I’m late to write this, but there’s something more powerful in sharing that four months later we’re still going strong. Bedtime is calm again, he’s proud of his space, and we feel like we have the tools to handle future transitions too. We’re so grateful for Molly and can’t recommend her enough!”
Mom of 3.5-Year-Old