Pineapple upside-down cake + boozy raspberry mash

Pineapple upside-down cake + boozy raspberry mash

I had plans for this week. Plans that included jumping on the popsicle bandwagon because it’s popsicle week and I have a really, really delicious three-ingredient, raw fudge pop recipe that I’ve been meaning to share for far too long. But then I posted a photo of pineapple upside-down cake and some of you lost your shit. Like, (one of you in particular) emailed me three times over the course of 24 hours-lost your shit. And then proceeded to tell me that if I didn’t post the recipe by the end of the week, OLC was going to be removed from your reader. THE HORROR. Although my typical (pre-wedding) response would have been this (what a bitchy feisty, little thing, I used to be), I crafted an email (accompanied by this GIF, instead) and explained that things have to be tested and photos have to be taken and then edited, and how all of that takes time that I currently do not have because I just got back from my wedding and am neck-deep in two too many ambitious projects that no one should try to tackle simultaneously. There was a day of no emails followed by an apology. And a half-joking, “Ok, I guess I’ll give you until next week.”

I laughed – so hard that I cried – because I realized that people can be so damn kooky (read: batshit crazy) when it comes to food. And I am no exception. I mean, I was so impatient at dinner the other night that I couldn’t wait for Thom to finish carefully spooning salsa over his tacos before barking SWEET BABY JESUS I AM EATING WITHOUT YOU! And then I devoured an entire taco before he took his first bite.

(They have a word for that sort of unsavory behavior. And it’s called being hangry.)

So here I am at 9PM on a Tuesday, eating dark chocolate nonpareils in bed and getting ready to binge watch start season three of OITNB (by the way, my friend wrote a brilliant piece on the show) (which I don’t recommend reading unless you’ve started season three or thoroughly enjoy spoilers, like me). But before I reacquaint myself with the fine ladies of Litchfield Penitentiary: Here ya go, Samantha. Here’s your pineapple upside-down cake that I spent all of Sunday morning photographing, for you. Then all of Monday evening – ignoring my husband (!) – so that I could edit the photos and compile them into this post, for you. And if you don’t make this cake and email me a photo of it (preferably while you’re shoveling it into your face) by tomorrow at midnight, I’m registering you for every Cute Kid Contest I can find on the internet.

I’m kidding. I’ll give you until 10AM, Thursday morning.

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Notes: I’ve made this cake with fresh raspberries and blackberries (the color from them doesn’t bleed the way the mash does), but prefer the texture and look of berries have been smashed with a bit of booze. I’ve also made this cake with both fresh and canned pineapple, and have to say I prefer pineapple that hasn’t been sitting on a grocery store shelf for six months. If you don’t want the topping to be too sweet, you can omit the coconut oil and reduce the brown sugar to one tablespoon, and simply sprinkle it over a lightly greased pan. And if you want your cake to be aesthetically pleasing (pineapple upside-down cakes are inherently ugly, you know), omit the oil + sugar topping and just lightly grease your baking pan and sprinkle with 2-3 teaspoons of brown sugar, instead.

And because this recipe wouldn’t have been possible without him: big thanks to Todd, the kind employee at my neighborhood Whole Paycheck Foods (SUP CAP HILL!) who dropped some serious pineapple knowledge on my ass while I was shopping for the perfect pineapple for this cake. And when the store didn’t have any Todd thought were suitable for baking (I took an unripened one home, anyway), he sent me on my way with one of their peeled + cored varieties, and is basically the only reason you’re looking at this recipe today (instead of two weeks from now).


Boozy raspberry mash
15-20 fresh raspberries
1 tablespoon golden (or spiced) rum

To assemble
2-4 tablespoons brown sugar
2 teaspoons refined coconut oil
5 fresh pineapple rings, about 1/2″ thick

Cake batter
1 3/4 cups (225g) all purpose unbleached flour
1/4 teaspoon baking soda
1/2 teaspoon baking powder
1/2 teaspoon fine sea salt
2/3 cup (148g) cane sugar
1 tablespoon (11g) potato starch

1/3 cup (68g) refined coconut oil, melted (but not hot)
1 1/2 teaspoons pure vanilla extract
1 tablespoon (14g) golden (or spiced) rum
1/2 cup (110g) soft silken tofu puree
1/2 cup (120g) pineapple juice

Preheat oven to 350˚F. In a small bowl, smash the raspberries with a fork and mix with rum; let sit for five minutes. Line an 8″ square baking pan with parchment paper. Lightly grease with oil then sprinkle with brown sugar and line with pineapple slices. Remove raspberries using a fork, making sure to shake off the excess liquid, then stuff into pineapple openings; set pan aside.

In a medium sized mixing bowl, sift together the flour, baking powder, baking soda, and salt; set aside. In a large mixing bowl, stir together the cane sugar and potato starch, then whisk in the coconut oil. Whisk for 30-45 seconds, just until the starch starts to act as a binder. Add the vanilla extract, rum, and tofu, and mix until combined. Stir in the pineapple juice and 2/3 of the flour mixture, and whisk until the clumps disappear. Using a spatula or wooden spoon, stir in the remaining flour. Pour batter over the pineapple slices and spread with the back of a spoon. Tap on counter to ensure the batter squeezes between the pineapple slices. Bake at 350˚F for 36-40 minutes, or until a toothpick comes out clean. Remove from oven and cover with a towel for at least 20 minutes, which will trap steam and ensure tenderness. Invert onto a wire rack and cool for at least an hour. Cake will keep for up to two days, but is best on the first day.

Yield: 10 slices


  • Reply valentina | sweet kabocha 14 July 2015 at 11:13 PM

    This cake seems gorgeous!!!

  • Reply Billy 14 July 2015 at 11:16 PM

    um that gb bird gif would’ve still been my response, purposely waiting until I was hangry to respond. I’m sad that there’s no popsicles, obvvss, but I’m also v turned on by this cake, so, ¯\_(ツ)_/¯

  • Reply Cady 14 July 2015 at 11:38 PM

    lolololololol you are a kind and patient soul.

  • Reply Maja 15 July 2015 at 1:49 AM

    What is happening?! 3 emails in 24 hours?! Over a cake? Hahaha… Thank you Samantha, for making my rainy morning a joyous one. And thank you Ash, for your gif genius. (those I get at least, unlike the emoji puzzle…) Btw, how scary is GB giving the finger??? Brrr, gives me the creeps. Well, he gives me the creeps with or without finger, but you know what I mean.

    • Reply Ashlae 15 July 2015 at 4:53 AM

      YO BABE –

      Yeah, Dubya is terrifying. You know what’s more terrifying? The fact that his brother and Donald Trump are top contenders for the republican presidential ticket. YIIIIIKES.

  • Reply Medeja 15 July 2015 at 3:21 AM

    It looks so good! Definitely tasted great too. I have never made upside down pineapple cake before! What a loss :D

  • Reply Kathryn 15 July 2015 at 3:44 AM

    If it makes you feel any better, last week my OH had the nerve (the nerve!) to go to the loo just after I said dinner was ready and by the time he sat down at the table, I’d already finished #hangry

    I don’t know what it is about pineapple upside down cakes that a) make me ridiculously happy and b) demand the addition of booze. Always a winner in my book.

    • Reply Ashlae 15 July 2015 at 4:59 AM

      SUP LADY –

      Ha! Thom has definitely pulled the bathroom stunt before. I actually just pick food off of his plate instead of eating mine.. but I’m thinking your strategy is much more conducive to the elimination of pre-dinner bathroom breaks.

  • Reply Erica 15 July 2015 at 4:28 AM

    This was literally the best thing to read on the Internet before 7 AM. You are hilarious and your photos are beautiful per usual.

  • Reply Katrina @ Warm Vanilla Sugar 15 July 2015 at 7:04 AM

    Oh man, that smash!!!! This cake looks incredible and those raspberries on top are totally calling my name!

  • Reply Cassie Tran 15 July 2015 at 7:27 AM


  • Reply Abby @ The Frosted Vegan 15 July 2015 at 7:35 AM

    Ha, why are people so crazy?! Kudos to you for keeping that shit together lady. Also, my fiance does the same thing, we will be ready, carrying our plates out to the living room (eat in front of the tv, no judging) and he’s all ‘Oh I have to go to the bathroom and pay these bills and read through Twitter’. UM NO. So I eat and it’s 9pm and he’s all ‘Why didn’t you wait?’ Because it’s my bedtime, BYE.

  • Reply Laura 15 July 2015 at 8:26 AM

    This is the best post I’ve ever read.

  • Reply Clem @ The Vegan Cookie Fairy 15 July 2015 at 8:37 AM

    LOL at this story and OM NOM at that cake. Any cake made with alcohol always gets my vote.

  • Reply Moran 15 July 2015 at 9:31 AM

    I cracked up.. You are the funniest food blogger I know. I just couldn’t stop laughing reading this and had to explain to my husband what the heck is so funny reading a recipe!
    And i’m so sad I found out from this post there’s a new season, when am I going to do the stuff I need to do??


  • Reply Kimiko 15 July 2015 at 10:33 AM

    Wow. That’s a whole new level of Crazy Eyes shit though. This looks unreal, as per usual :)

  • Reply Heidi 15 July 2015 at 10:56 AM

    This post literally made me laugh out loud. I agree that pineapple upside down cakes are flat out ugly, but this one is so, so, soooo dreamy I can hardly stand it. Your gif game is on point, by the way. I am so stealing that G Dub one for my personal arsenal.

  • Reply Kayla 15 July 2015 at 11:28 AM

    Ha! I love that you just put her on blast. Do let us know how many Cute Kid contests you ended up registering her for. ;) The cake looks amazing, btw!

  • Reply Alana 15 July 2015 at 11:51 AM

    All I wanna do right now is high five you, a couple times. The story of this cake is gonna stay with me forever and I’m pretty sure I’ll think of you (and Samantha) every time I see a pineapple upside down cake. Also, Thom and his carefully spoon salsa. Been there, although my bark wasn’t as friendly as yours! Basically, I like your style!!

  • Reply Sarah | Well and Full 15 July 2015 at 1:05 PM

    I couldn’t stop laughing while I was reading this post (which normally would be fine, but as I’m sitting at my cubicle right now, was rather inopportune). But, like many other commentors, I must also thank Samantha for her persistence in requesting this lovely cake ;)

  • Reply J.S. @ Sun Diego Eats 15 July 2015 at 2:11 PM

    A) That story was the best. Apparently you do negotiate with terrorists? Haha

    B) The layout of the pictures in this post is so SO beautiful.

  • Reply Elizabeth 15 July 2015 at 3:27 PM

    pineapple? MORE LIKE FINEAPPLE!

  • Reply Kasey 15 July 2015 at 4:15 PM

    Serious pineapple knowledge >>> this totally made me smile :) x

  • Reply steph 15 July 2015 at 5:05 PM

    girl, your pineapple rings are on point! whenever i peel a pineapple i freehand it but i think the next time i’m going to have to break out the cookie cutters because your pineapple perfection is calling to me. ditto your gorgeous photos! only you could make pineapple cake look like perfection!

    ps – i feel like this was a bitch, where’s my cake kinda business and as much as samantha is one cray lady, i gotta say, props to her!
    pps – once all the food is on the table, it’s a free for all, salsa spooning be damned!

  • Reply Grace 15 July 2015 at 8:19 PM

    HA! This post is fantastic. Because someone is crazy enough to threaten you over cake, the GIFs duh, your kind response and how you left it with a challenge. I hope Samantha owns up to it. I feel like she has to.

  • Reply Dawn 15 July 2015 at 10:17 PM

    You are seriously funny (tell us did she reply??) OLC… always entertaining. A belated congratulations on your wedding.

  • Reply Abby 16 July 2015 at 5:30 PM

    Hahah, this post is amazing, Ashlae! Your story cracked me up. Those gifs!
    Anyways, this cake is crazy stunning. Loving it. <3

  • Reply Jana du Plessis 17 July 2015 at 2:22 AM

    Your words and humour. It brightens my day every time!

  • Reply gabby 17 July 2015 at 11:41 AM

    Do you think it would be fine to sub corn starch for the potato starch?

  • Reply Happy Weekend + Links I Love | DonzWebb 17 July 2015 at 5:51 PM

    […] + Treat yourself: Campfire Baked Bananas and Pineapple Upside-Down Cake + Boozy Raspberry Mash. […]

  • Reply Jordan 18 July 2015 at 1:06 AM


    The cake looks great, absolutely, yes, okay.
    But let’s be honest: the real star of this particular recipe is a wit that I CANNOT EVEN HANDLE (in the best sense). I was making your cherry/almond granola recipe last night and thought to myself, “If I have a spirit animal, it’s probably this Ashlae person that I keep coming across.”

    Reading this now, I think the Jordan from last night was right.
    Thanks for being so, damn, genuinely, funny.

  • Reply Teresa N. 18 July 2015 at 12:19 PM

    I saw this, and was secretly hoping you’d post this! Can’t wait to make this!

  • Reply Sunday Best | wild heart of life 19 July 2015 at 3:04 PM

    […] as Ashlae. Also, I have never encounter a blogger with such an ability to basically inspire a cult following. But can you really blame us? Try not be obsessed with her incredible recipes and […]

  • Reply Laura (Blogging Over Thyme) 20 July 2015 at 3:59 PM

    This is so beautiful!!!!! Need to make it!

  • Reply Lauren 21 July 2015 at 10:50 PM

    I’m into spoilers too. And this cake.

  • Reply Felicia@Ingredient1 22 July 2015 at 2:08 PM

    Beautiful recipe, the cake looks absolutely divine. Love that you are using tofu puree; is there a specific brand you like to use for baking?

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