I spend an unreasonable amount of time wondering what, exactly, will happen if I swap one braising medium for something that has absolutely no business being in a Dutch oven. Most of the time, those experiments stay in my notebook and never make it to the stove. But this one did: two fresh August zephyr squash halves, a pot full of cold chocolate pudding, a scattering of whole dried savory leaves, and about 2 heaping tablespoons of miso paste where chicken stock would normally go. Forty-five minutes later, I had a very clear answer.

The short version is that it was edible in the technical sense, fascinating in the kitchen-science sense, and not something I’d serve to anyone I liked. Still, if you’re curious about how delicate summer squash behaves when braised in a thick sweet dairy-and-starch mixture with salty fermented soybean paste and woody herbs, I took careful notes. Here’s exactly what I used, what changed minute by minute, how it smelled, how the texture shifted, why the method behaved the way it did, and what I’d do instead if the goal were actually dinner.

1. The setup: what went into the pot

I started with 2 medium zephyr squash, about 7 inches long each, picked up at a late-August farm stand. Zephyr squash, if you haven’t cooked with it, is a two-tone summer squash with a pale green stem end, yellow blossom end, thin skin, and a texture somewhere between zucchini and yellow squash. These weighed roughly 12 ounces each. I halved them lengthwise and left the seeds and skin intact.

For the braising medium, I used 4 cups of prepared chocolate pudding straight from the refrigerator, 2 heaping tablespoons of white miso paste, and 1 tablespoon whole dried savory leaves. The pudding was thick, glossy, and fully set before it went into the pot. I whisked the miso into it only loosely, so there were still beige streaks throughout. Then I scattered in the savory leaves and nested the squash halves cut-side down so they were completely submerged.

2. Why this was a strange braise from the start

A normal braise works because the cooking liquid is fluid enough to transfer heat evenly and gentle enough to soften food over time without scorching. Chicken stock, wine, tomato, coconut milk, or even water all move around the food as they heat. Cold pudding does not. Pudding is thickened with starch, often cornstarch or modified food starch, and in a chilled state it sits more like a loose custard than a liquid.

That meant the squash wasn’t really braising in the classic sense. It was more like being slowly heated inside a sweet, dense blanket. Add miso, which brings salt and glutamates, and whole dried savory, which is resinous and slightly peppery, and the flavor profile was already pulling in three directions at once: dessert, soup base, and herb garden.

3. The first 10 minutes: almost no movement

I put the pot over low heat for the first 10 minutes because I was worried the pudding would catch on the bottom. That instinct was correct. At minute 5, the mixture had barely relaxed. The surface looked the same as when it was cold, except for a few shiny patches where the pudding began to loosen around the edges of the pot.

At minute 10, I could smell warm cocoa first, then a wave of toasted soybean funk from the miso. The savory leaves had not infused so much as hovered there, smelling like dry pantry herbs steeping in hot dessert. The squash themselves smelled faintly green, but they were still structurally firm when I nudged one with tongs.

4. Minutes 10 through 25: the pudding split personality begins

Once the pot reached a steadier simmer, the pudding changed in a very odd way. The portion nearest the bottom thinned out first, while the upper layer remained thick. Instead of a uniform sauce, I got a two-layer system: a looser, darker chocolate slurry underneath and a heavier cap above. That’s the opposite of what I want in a braise, because the heat was concentrated at the base and corners.

By minute 20, the miso had mostly dissolved. The savory leaves, however, stayed whole and papery. Unlike bay leaves, which are usually removed and don’t pretend to become tender, dried savory crumbles into abrasive little flecks. Those flecks got trapped against the squash skin and in the seed cavity. The aroma by this point was deeply confusing: brownie batter, instant gravy, and dried thyme’s sharper cousin.

5. At 30 minutes, the squash started giving up water

Summer squash are mostly water. Zephyr squash typically soften quickly in sauté pans and roasts because their flesh releases moisture as cell walls break down. Around the 30-minute mark, that happened here too. The squash halves had gone from rigid to slumped, and I could see pale yellow juices leaking into the chocolate mixture.

That water release mattered. It diluted the pudding around the squash, making pockets of thinner liquid that finally behaved a little more like a braise. Unfortunately, it also created a muddier flavor. Instead of rich chocolate, I now had watery cocoa vegetable gravy with salty miso notes. The squash were soft enough to pierce with a paring knife, but not collapsing yet.

6. What happened at 45 minutes exactly

At minute 45, I lifted out the squash halves one by one. They were fully cooked through, but in the least flattering way possible. The cut sides had turned a tan-brown color from the cocoa, while the skins looked dull and olive-yellow. The flesh near the seed cavity was mushy. The outer 1/4 inch held together, but the centers were close to spoon-soft.

The pudding mixture itself had transformed into something between sauce and paste. It was no longer the tidy, smooth pudding I started with. It looked broken and grainy, with tiny curds where the dairy proteins and starch had tightened and with swollen herb fragments throughout. The miso had darkened the mixture and amplified the savory smell, but it didn’t make the dish taste balanced. It made it taste louder.

7. The taste test: worse than the smell, which was already a problem

I tasted the squash first without sauce. On their own, they were bland but not offensive, just overcooked. Then I dragged a forkful through the braising medium. The first hit was sweet milk chocolate, immediately followed by a salty, fermented punch from the miso and then a dry, almost dusty herbal bitterness from the savory leaves.

The biggest problem was sequence. Good flavor combinations overlap and resolve. This one arrived in clashing stages. Sweet, salty, herbal, vegetal, and faintly beany all took turns instead of working together. The finish was especially awkward: cocoa powder and cooked squash water. I took three bites to be fair. None improved with repetition.

8. The texture was the real disaster

If flavor had been the only issue, I might have called it a strange but instructive failure. Texture made it much worse. Braised squash should be silky, tender, and easily cut with a spoon while still retaining shape. These halves were patchy. The outer edges were intact; the inner flesh had gone mealy. That often happens when summer squash sit too long in heat without enough structure-preserving support from quick cooking or dry roasting.

The sauce clung in a thick layer rather than coating smoothly. Because the pudding starch had thickened, loosened, and then concentrated again during heating, it left a pasty film on the tongue. Every so often, a whole dried savory leaf or stem fragment interrupted things with a scratchy bite. There are many kitchen mistakes I can forgive. Gritty pudding-sauce on mealy squash is not one of them.

9. Why the chemistry worked against me

Three things sabotaged the result. First, pudding is designed for cool, stable spooning, not prolonged stovetop cooking around vegetables that release water. Second, zephyr squash are delicate and low in starch, so they don’t absorb and transform the way potatoes, winter squash, or eggplant can. Third, miso is powerful but not magical; it adds savoriness, but it can’t unify chocolate and summer squash on its own.

The dried savory was also the wrong herb form for the job. Whole dried leaves need enough free liquid and time to hydrate and infuse. In thick pudding, they basically steeped poorly while retaining their rough texture. If I had used a tiny pinch of finely ground savory, the herb issue would have been less aggressive, though the dish still would not have been good.

10. Was there anything redeeming about it?

Yes, but only if I’m being generous and wearing my “food experiment” hat instead of my “what’s for supper” hat. The squash did remain recognizable after 45 minutes submerged in a thick, unconventional medium, which is mildly interesting. Also, the miso prevented the pudding from tasting purely dessert-sweet once heated. It shifted the whole thing toward something savory-adjacent, even if that direction was not pleasant.

I’ll also say this: the kitchen smelled memorable. Not good, exactly, but memorable. If you enjoy those moments where a recipe teaches you something through failure, this one did clarify the limits of ingredient substitution in a very efficient way.

11. What I would change if I wanted to salvage the idea

If the core curiosity is “Can chocolate be used with squash in a savory context?” the answer is yes, but not with cold pudding as the braising liquid. I would start with 1 1/2 pounds cubed roasted delicata or kabocha squash, not zephyr squash, because both have denser flesh and natural sweetness that can stand up to cocoa.

Then I’d build a sauce with 1 tablespoon unsweetened cocoa powder, 2 cups vegetable or chicken stock, 1 teaspoon miso, 1 small shallot, 1 clove garlic, and perhaps 1/4 teaspoon chile flakes. That gets you into the territory of mole-inspired flavors rather than pudding casserole chaos. Fresh savory or thyme could work in a very restrained amount, but I would strain the sauce or mince the herbs finely.

12. What I would do with zephyr squash instead

Zephyr squash are at their best with fast, high-heat cooking. My preferred method is to slice them into 1/2-inch half-moons, toss with 1 tablespoon olive oil and 3/4 teaspoon kosher salt per pound, and roast at 425°F for 16 to 20 minutes. They stay tender but not soggy, and the edges pick up a little color.

If I want something brothier, I’ll braise them briefly in 1 cup stock with 1 tablespoon butter, a smashed garlic clove, and a strip of lemon zest for 6 to 8 minutes, not 45. Finish with herbs off the heat. Summer squash reward restraint. They are not built for extended punishment in experimental pudding baths.

13. Cost of the experiment versus value of the lesson

This was not an especially expensive failure, which made it easier to laugh about. The two squash cost about $4 at the farm stand. The pudding, miso, and dried savory amounted to another $4 to $6 depending on brand and pantry math. So call it an $8 to $10 lesson, plus 45 minutes of active curiosity and another 10 minutes of washing a pot lined with chocolate-miso residue.

As lessons go, I’ve paid more for worse information. Now I know, with confidence, that “submerge and braise in pudding” belongs in the category of things that sound amusing in a headline but should rarely proceed to execution.

14. My final verdict

What happened after 45 minutes was not a miracle transformation, nor a secret chef trick, nor an unexpectedly brilliant fusion dish. The zephyr squash became over-soft and waterlogged, the chocolate pudding turned grainy and pasty, the miso made everything saltier and stranger, and the whole dried savory leaves contributed a rough herbal bitterness that never integrated.

If you’re here for the honest answer, here it is: it failed, and it failed in a very specific, educational way. I’m glad I tried it once so you don’t have to. Save the zephyr squash for roasting, save the miso for broths and glazes, save the savory for beans or poultry, and save the chocolate pudding for a bowl, a spoon, and absolutely no contact with summer squash.