Boston Cream Pie Stuffed Hawaiian Rolls
How This Wacky Idea Became My Party Trick
Honestly, if you told me five years ago I’d be stuffing sweet Hawaiian rolls with homemade pastry cream and dousing them in chocolate ganache, I’d have laughed you right out of my kitchen, probably getting powdered sugar everywhere in the process. But there I was at one of those neighborhood potlucks—picture kids running feral and adults pretending they don’t know who’s responsible for the suspicious casserole—and I needed something quick, impressive, and, let’s be real, not another spinach dip. So I mashed up my love for Boston Cream Pie (which, let’s face it, is honestly more cake than pie) with everyone’s weird obsession with Hawaiian rolls. Voilà. Now they’re my signature, and I’m slightly worried the neighbors only invite me for these. (Fine by me!) Oh, and if you sneak one before dinner, I promise I won’t tell.
Why You’ll Love This—Or, Why My Family Begs For Them
I make this when I’m in the kind of mood where I want to eat dessert but also want a no-fuss baking day. My family goes a little wild for these because they’re bite-sized (you can totally have three and pretend it’s not a big deal), and honestly, who doesn’t love a surprise? There was a time I tried using whipped cream instead of pastry cream—just don’t. It oozes everywhere; cleaning up sticky floors is not my favorite. But make these for a birthday, movie night, or even breakfast (hey, no judgment here)—they disappear faster than you can say “who took the last one?”
The Stuff You’ll Need—Don’t Panic
- 12 Hawaiian rolls (I use King’s sometimes, but whatever’s on sale works. My grandmother swore by the round ones, but the rectangular pack is easier to stuff, honestly.)
- 1 packet instant vanilla pudding mix (about 102g, but sometimes I just eyeball it)
- 1 cup cold milk (I’ve swapped in oat milk when that’s all we’ve got. Works, but a bit…earthy.)
- 1 cup heavy whipping cream (Skip if you’re using the shortcut below.)
- 2 tbsp powdered sugar
- 1 tsp vanilla extract (Real or fake, I promise I can’t always tell)
- 1/2 cup semi-sweet chocolate chips (Or dark. Or milk. My kid once used white chocolate and, eh, it worked.)
- 2 tbsp butter
- Pinch of salt (I sometimes forget this, not the end of the world)
- Optional: If you can’t be fussed, swap the pudding mix and milk for a tub of store-bought custard. I’ve totally done that. No shame.
Let’s Get Our Hands Messy: Directions
- Get that pastry cream ready. In a bowl, whisk the pudding mix and cold milk for like 2 minutes until thick. Let it sit in the fridge while you do other stuff. (If you used a tub of custard, just give it a stir and grab a spoonful for, uh, quality control.)
- Whip the cream (skip if you’re in a rush). Use a mixer to beat heavy cream, powdered sugar, and vanilla until stiff peaks show up. Actually, I sometimes overbeat it and end up with something closer to butter—so keep an eye out. Fold that into your chilled pudding. If you skipped whipping, your filling will be a little denser—not the worst thing!
- Let’s hollow out the rolls. Grab those Hawaiian rolls and, using a paring knife or your finger (after washing, please), poke a small hole in one side. You’re not performing surgery, just making space for filling. Don’t stress over perfection; I never do.
- Stuff ’em! Dig out a piping bag (or just a zip-top bag with the corner snipped—been there) and spoon in your pastry cream. Squeeze a generous blob into each roll. This is where I usually sneak a taste. If you overfill and the roll cracks a bit—eh, just eat that one first.
- Chocolate time. Melt butter and chocolate chips together. I do this in 20-second microwave bursts, stirring in between. It’ll look a hot mess at first—just keep stirring and don’t panic, it comes together. Throw a pinch of salt in. Let it cool for a minute so it thickens up a bit.
- Dunk (or drizzle) the tops. You can dip the tops of each stuffed roll into the chocolate ganache, or be a rebel and just spoon it over. If it drips down the sides…well, that’s pretty.
- Chill out. Pop the finished rolls into the fridge for 20-30 minutes so the ganache sets. Actually, if you eat one right away, I won’t judge. Sometimes patience just isn’t in the cards, you know?
Notes—Not Everything Goes According to Plan
- The ganache sometimes ends up too thick. I just microwave it for another few seconds and add a splash of milk. If it gets runny…back to the fridge.
- Don’t stress if your holes are wonky. After chocolate, nobody notices!
- Once I used low-fat milk for the pudding—tasted fine to me, but the texture was, well, a bit sadder than usual. Go full-fat if you can.
- If your rolls seem dry, just brush ’em with a little extra cream or milk before stuffing. Actually makes a difference.
Some Variations (and a Fail or Two)
- I’ve tried coffee-flavored ganache instead of straight chocolate. Heavenly with an after-dinner espresso.
- Once swapped Nutella for the ganache—it was rich, but my aunt grumbled it was “too modern.” There’s no pleasing everyone.
- Tried jam-filled once. Don’t. The whole thing got soggy and tasted oddly…fermented?
- You can make these mini by cutting rolls in half and using a melon baller to scoop out middles—just messier, that’s all.
What You’ll Need—And What To Do If You Don’t Have It
- Hand mixer (or an old-fashioned whisk and some elbow grease—seriously, I’ve done it and it’s a workout, but it works if you’re desperate or just feeling nostalgic)
- Piping bag—or a sandwich bag with the tiniest corner snipped. In a pinch, a spoon just jammed in there kinda works, too (but it’s messy; just saying)
- Microwave safe bowl for ganache, or you could use a double boiler if you’re feeling fancy (I rarely do, but hey, sometimes you want to feel like Julia Child)
How To Store These Beauties (If They Last That Long)
Stick ’em in a container and keep in the fridge. Technically, they’ll be good for about two days, though honestly, in my house it never lasts more than a day! I actually think they taste better the next morning—if you can believe it, the flavors meld or whatever. Only, if you’re taking them to a party, pack some extra napkins—the chocolate tends to melt a bit if you drive too long (ask me how I know).
How I Like To Serve Boston Cream Pie Stuffed Hawaiian Rolls
I usually plop these right in the middle of the table on a big plate. Sometimes with a dusting of extra powdered sugar (looks cute, gets everywhere). Once, for my nephew’s birthday, we popped in some candles and pretended they were mini-cakes, which caused a lot of giggling and way too much running around. Also, if I’m feeling like “hostess with the mostest,” I’ll serve with coffee or even some fancy iced coffee—not that anyone needs caffeine after all this sugar, but hey, we live dangerously.
Things I Wish I’d Known Sooner (Pro Tips, Kinda)
- I once tried rushing the chilling step and regretted it because the chocolate just smeared everywhere instead of firming up.
- Too much filling and the rolls sort of explode from the seams. Now I do a little less, and sneak any leftovers with a spoon (cook’s treat).
- I tend to think using the best rolls makes a difference, but on second thought, most folks can’t tell the difference at all. Don’t stress.
Questions People Actually Ask Me (No Judgment)
Can I make these ahead?
Absolutely. Just keep them cold so the filling’s solid—otherwise it’s like chasing pudding across your hand. They’re great the next day, maybe even better?
Do I really need a piping bag?
You don’t! A zip-top bag works, or, if you’re handy, a spoon and some patience. Honestly, it’s not rocket science (just a little messier with the spoon, so keep a napkin nearby).
What if I want to make these dairy-free?
I’ve tried with almond milk pudding and vegan chocolate chips. They’re totally edible, maybe just a touch less creamy. You can also check this vegan ganache recipe that I tried once and nobody noticed the difference.
How do I keep the chocolate from getting dull?
If you care about shiny chocolate, let the ganache cool a bit before dunking rolls and store them uncovered in the fridge for the first half hour. But, between you and me, nobody at my house notices.
And, just by the way, if you ever find yourself with extra filling and chocolate, you can layer them in a glass, sprinkle with crumbled cookies, and eat it with a spoon. Not really Boston Cream Pie Stuffed Hawaiian Rolls, but tell that to my midnight snack brain. Not everything needs to be Pinterest-perfect, right?
Ingredients
- 12 Hawaiian sweet rolls
- 1 cup vanilla pudding
- 1 cup heavy cream
- 4 oz semi-sweet chocolate chips
- 2 tbsp unsalted butter
- 1/4 cup powdered sugar
- 1 tsp vanilla extract
- Pinch of salt
Instructions
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1Slice the Hawaiian rolls in half horizontally without separating them completely; place the bottom halves on a serving tray.
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2In a bowl, whisk vanilla pudding, powdered sugar, and vanilla extract until smooth. Spread or pipe the mixture evenly onto the bottom halves of the rolls.
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3Place the top halves of the Hawaiian rolls over the pudding layer to sandwich the filling.
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4In a microwave or saucepan, heat heavy cream until just simmering, then pour over chocolate chips and butter. Stir until smooth, creating the chocolate ganache.
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5Spoon or drizzle the chocolate ganache generously over the tops of the stuffed rolls. Sprinkle a small pinch of salt if desired.
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6Refrigerate for at least 15 minutes to set. Serve chilled or at room temperature.
Approximate Information for One Serving
Nutrition Disclaimers
Number of total servings shown is approximate. Actual number of servings will depend on your preferred portion sizes.
Nutritional values shown are general guidelines and reflect information for 1 serving using the ingredients listed, not including any optional ingredients. Actual macros may vary slightly depending on specific brands and types of ingredients used.
To determine the weight of one serving, prepare the recipe as instructed. Weigh the finished recipe, then divide the weight of the finished recipe (not including the weight of the container the food is in) by the desired number of servings. Result will be the weight of one serving.
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