I fell in love with these pineapple cookies the first time I tasted a warm one—thin, buttery pastry melting against a dense, tangy pineapple center. They’re small, jewel-like, and more reliable than any fancy pastry when I need crowd-pleasing cookies for the holidays or a quiet afternoon with tea.

This recipe is hands-on but not fussy. You’ll make a long-simmered pineapple filling, cream a simple butter dough, and sandwich them together into perfectly sealed rounds. The technique is straightforward; the rhythm of making them is almost meditative.

If you want consistent results, measure, follow the steps in order, and keep the filling chilled before assembly. Below I’ll list exactly what I use, how I do each step, common missteps and simple fixes, plus tips that save time without compromising texture or flavor.

What You’ll Gather

Below are the exact ingredients called for in the recipe. Each line includes a quick note about its role or a tip I use when I bake these.

Ingredients

3sticks (350 g)butter,or unsalted butter, at room temperature — Provides the tender, rich base of the dough; room temperature ensures smooth creaming.
3 1/2oz (100g)sweetened condensed milk — Adds sweetness and a silky texture to the dough during creaming.
2egg yolks — Help bind the dough and add richness (this is the first set of egg yolks in the dough).
18oz. (510g)all-purpose flour,or plain flour — Structure for the cookie; mix just until a soft dough forms.
16lbs (7 kg)whole pineapples,2 whole / 3 1/2 kg or 5 lbs. (2 1/2 kg pineapple flesh) — The raw fruit called for to make the filling; you’ll puree and reduce it down.
1/2tablespooncloves,optional — Optional warming spice for the filling; remove and discard before chilling.
1 – 1 1/2cupssugar,or to taste — Sweetens and helps the puree reduce to a thick jam; adjust to pineapple sweetness.
1tablespoonlemon juice — Brightens the filling and balances sweetness.
2egg yolks — The second set used to make the egg wash for glazing the cookies.
1/4teaspooncondensed milk — Added to the egg wash for sheen and slight sweetness.
1/2teaspoonoil — Added to the egg wash to help it spread thinly and evenly.

Pineapple Cookies (Pineapple Tarts): How It’s Done

Prepare the pineapple: cut off the stalks, peel the pineapple(s) called for in the Ingredients, remove all “eyes” (divots) and the core, then chop the flesh into pieces. Place the pineapple pieces in a blender and puree until smooth.
Make the pineapple filling: combine the pineapple puree and the optional 1/2 tablespoon cloves in a non-stick pot over medium heat. Stir constantly to prevent sticking and burning. When the puree has reduced and is almost dry, add 1–1 1/2 cups sugar (or to taste) and 1 tablespoon lemon juice. Lower the heat to a gentle simmer and continue stirring until the mixture turns golden and becomes very sticky and thick. Remove and discard the cloves. Transfer the filling to a bowl and chill in the refrigerator for 30 minutes to firm.
Make the dough: in a mixing bowl, cream 3 sticks (350 g) butter and 3 1/2 oz (100 g) sweetened condensed milk together until light and fluffy. Add the first set of 2 egg yolks, one at a time, beating until each is incorporated. Gradually add 18 oz (510 g) all-purpose flour and mix just until a soft dough forms and it no longer sticks to your hands.
Prepare the egg wash: in a small bowl whisk together the second set of 2 egg yolks, 1/4 teaspoon condensed milk, and 1/2 teaspoon oil until smooth.
Portion the filling and dough: divide the chilled pineapple filling into 100 equal portions and roll each portion into a small ball. Divide the dough into 100 equal portions and roll each into a ball.
Assemble each cookie: flatten a dough ball with your palm into a small disc. Place one pineapple filling ball in the center, bring the dough edges up to fully enclose the filling, pinch to seal, and gently roll the sealed piece into a smooth round. Place each finished cookie seam-side down on a baking sheet lined with parchment paper. Leave space between cookies.
Score and glaze: lightly press a criss-cross pattern into the top of each cookie using the back of a paring knife. Brush the tops with a thin coat of the prepared egg wash, then brush a second thin coat.
Bake: preheat the oven to 330°F (165°C). Bake the cookies for 20–22 minutes, or until they turn golden brown on top.
Cool and store: remove the baking sheet from the oven, transfer the cookies to a wire rack to cool completely, then store in an airtight container.

Why It’s My Go-To

These cookies hit a reliable sweet-sour note thanks to the reduced pineapple filling. The butter-forward dough provides a clean, tender contrast that keeps the filling from dominating. They’re small, so one or two feel like a treat rather than a commitment—perfect for hosting and gifting.

They also scale well: the recipe’s assembly-focused steps make it easy to turn a long simmering session into dozens of finished cookies. I keep the filling chilled so the assembly is fast and tidy—no sticky mess, just steady production.

Smart Substitutions

Substitutions can help when you don’t have something on hand, but keep texture and moisture in mind.

Butter — The recipe calls for butter. If you must, use unsalted butter as noted so you can control salt. Avoid margarine; it changes texture.
Condensed milk (in dough and egg wash) — The amounts are small; you can omit the 1/4 teaspoon in the egg wash in a pinch but keep the 100 g in the dough for sweetness and body.
Pineapple — Fresh pineapple is specified. Canned crushed pineapple will alter moisture and may require longer reduction—use fresh for best texture.
Cloves — Optional. If you prefer a different warm note, a small pinch of cinnamon or ground ginger can work, but use sparingly.

Recommended Tools

These tools make the process smoother and more consistent.

Sharp chef’s knife and sturdy cutting board — for peeling and coring the pineapples neatly.
High-speed blender or food processor — to puree pineapples smooth before reduction.
Non-stick heavy-bottomed pot — ensures even reduction with less chance of burning.
Mixing bowl and hand or stand mixer — to cream butter and condensed milk until light.
Baking sheets lined with parchment — prevents sticking and promotes even browning.
Digital scale — the recipe uses many exact weights; a scale keeps portions consistent.
Wire rack — for cooling cookies completely before storage.

Missteps & Fixes

Small problems come up often with filled cookies; here’s how I recover.

Filling too wet after reduction — Continue simmering until very thick and sticky as instructed. If it still feels loose after cooling, return to the pot on low heat and reduce gently until it reaches a firmer jam-like stage.
Filling oozes during baking — That usually means the filling was too warm at assembly or the dough seals weren’t tight. Chill the filling until firm and pinch dough seams thoroughly; roll the sealed piece to smooth any gaps.
Dough cracks when sealing — Dough that’s too cold or too dry will crack. Keep dough at room temperature if it’s stiff; if it’s crumbly, press gently with fingertips to bring it together without adding extra flour.
Cookies brown unevenly — Rotate sheets midway through bake and ensure even spacing. Use the middle rack when possible.

Fresh Takes Through the Year

Small seasonal tweaks keep these cookies interesting.

Winter — Add the optional cloves or a tiny pinch of ground cinnamon to the filling for warmth.
Summer — Use very ripe pineapples for more pronounced tropical sweetness; reduce sugar slightly if fruit is exceptionally sweet.
Gift styling — Dust cooled cookies lightly with powdered sugar and stack in parchment-lined tins for a polished presentation.

Pro Tips & Notes

Timing and temperature

Chilling the filling for 30 minutes as instructed is a small step that pays off huge dividends during assembly—it prevents tears and leaks. Dough should be soft but not sticky; if it clings to your hands, a brief rest in the fridge can help, but avoid making it cold and hard.

Portioning

Portioning into 100 pieces produces small, elegant cookies. Use a scale and weight each portion for speed and consistency. If you prefer larger tarts, scale portions proportionally and extend baking time a few minutes, watching for golden tops.

Make-Ahead & Storage

The pineapple filling can be made ahead and kept chilled for up to 3 days in the refrigerator; for longer storage, freeze it in portions. Dough can be made, shaped into a log, wrapped tightly, and refrigerated for up to 48 hours or frozen for longer. Assemble from chilled components for best results.

Once baked and cooled, store cookies in an airtight container at room temperature. They keep well for several days—short-lived because they’re delicious, not because they go bad quickly.

Quick Questions

Can I use canned pineapple? — Fresh is specified for texture and moisture control. Canned will work only if you further reduce the puree to remove extra liquid; expect a longer cook-down.
Why two separate sets of egg yolks? — The first two go into the dough for richness and binding; the second two are for the egg wash to glaze the tops.
Do I have to use cloves? — No. They’re optional. If you use them, remove the whole cloves before chilling the filling.

Bring It to the Table

Serve these cookies at room temperature. They pair beautifully with black tea or a mild coffee. For a gift, arrange them in a single layer inside a tin with parchment paper to prevent sticking. If you’re bringing them to a party, a shallow platter with a few sprigs of fresh mint or citrus peel adds a bright contrast to the buttery golden tops.

Make a batch, practice the sealing a few times, and you’ll find a rhythm. The payoff is simple: small cookies that taste elaborate and feel like homemade comfort each time.

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Best-Ever Pineapple Cookies (Pineapple Tarts)

Buttery cookie dough filled with a thick, caramelized pineapple filling—classic pineapple tarts made into small cookies.

Prep Time2

Cook Time20

Total Time2 20

Course: Dessert

Servings: 12 cookies

Ingredients

3 sticks 350 gbutter, or unsalted butter, at room temperature
3 1/2 oz 100 gsweetened condensed milk
2 egg yolks
18 oz. 510 gall-purpose flour, or plain flour
16 lbs 7 kgwhole pineapples, 2 whole / 3 1/2 kg or 5 lbs. (2 1/2 kg pineapple flesh)
1/2 tablespooncloves optional
1 – 1 1/2 cupssugar or to taste
1 tablespoonlemon juice
2 egg yolks
1/4 teaspooncondensed milk
1/2 teaspoonoil

Instructions

Prepare the pineapple: cut off the stalks, peel the pineapple(s) called for in the Ingredients, remove all "eyes" (divots) and the core, then chop the flesh into pieces. Place the pineapple pieces in a blender and puree until smooth.
Make the pineapple filling: combine the pineapple puree and the optional 1/2 tablespoon cloves in a non-stick pot over medium heat. Stir constantly to prevent sticking and burning. When the puree has reduced and is almost dry, add 1–1 1/2 cups sugar (or to taste) and 1 tablespoon lemon juice. Lower the heat to a gentle simmer and continue stirring until the mixture turns golden and becomes very sticky and thick. Remove and discard the cloves. Transfer the filling to a bowl and chill in the refrigerator for 30 minutes to firm.
Make the dough: in a mixing bowl, cream 3 sticks (350 g) butter and 3 1/2 oz (100 g) sweetened condensed milk together until light and fluffy. Add the first set of 2 egg yolks, one at a time, beating until each is incorporated. Gradually add 18 oz (510 g) all-purpose flour and mix just until a soft dough forms and it no longer sticks to your hands.
Prepare the egg wash: in a small bowl whisk together the second set of 2 egg yolks, 1/4 teaspoon condensed milk, and 1/2 teaspoon oil until smooth.
Portion the filling and dough: divide the chilled pineapple filling into 100 equal portions and roll each portion into a small ball. Divide the dough into 100 equal portions and roll each into a ball.
Assemble each cookie: flatten a dough ball with your palm into a small disc. Place one pineapple filling ball in the center, bring the dough edges up to fully enclose the filling, pinch to seal, and gently roll the sealed piece into a smooth round. Place each finished cookie seam-side down on a baking sheet lined with parchment paper. Leave space between cookies.
Score and glaze: lightly press a criss-cross pattern into the top of each cookie using the back of a paring knife. Brush the tops with a thin coat of the prepared egg wash, then brush a second thin coat.
Bake: preheat the oven to 330°F (165°C). Bake the cookies for 20–22 minutes, or until they turn golden brown on top.
Cool and store: remove the baking sheet from the oven, transfer the cookies to a wire rack to cool completely, then store in an airtight container.