These sugar plum cookies are soft and chewy cookies, dipped in a colored syrup and rolled in sugar. They're filled with a homemade, fragrant sweet plum jam. The cookie dough is made with olive oil to keep them soft and chewy, as well as adds a subtle earthy flavor (if you don't like olive oil you can use a more neutral flavored oil). Spices infused into the plum jam give a subtle warm spiced flavor that doesn't taste spicy. They're perfect to make and so festive for Christmas and the holidays since the syrup and jam keep them soft and delicious for days! I made these cookies for my Nutcracker Christmas cookie boxes.
These cookies are inspired by Italian wedding peach cookies. I made two other versions of cookies inspired by Italian wedding peach cookies: my Italian lemon cookies and my peach Italian cookies.

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🧚♂️ Why you'll LOVE this recipe
- Sugared plums: These cookies look like plums covered in sugar! So cute and festive for the holidays.
- Plum jam center: The filling is a delicious, fragrant vanilla plum jam, infused with cinnamon and cardamom for a subtle spice.
- Olive oil cookies: Fragrant, slightly earthy olive oil cookies that are soft and cake-like. They're almost like individual filled pastries.

📝 Key ingredients
Read through for all the tips you will need for success!
Full steps and ingredients in recipe card below.


- Extra virgin olive oil: I like how these lemon cookies have a subtle olive oil flavor, so I opted for an extra virgin olive oil with a more robust flavor. If you don't like the flavor of olive oil, you can choose a light olive oil or even a vegetable oil.
- Eggs: This recipe requires two eggs for the perfect texture that's a cross between a pastry and a cookie.
- All purpose flour: Weigh the flour to get the most accurate results. If you don’t have a scale, measure properly by stirring the bag and spooning gently into a measuring cup. Scrape the excess off the top with the flat edge off a knife without packing it into the cup.
- Milk: Since this cookie recipe is more of a pastry as opposed to a classic butter cookie, the cookie dough requires a few tablespoons of milk to help it come together.
- Rosemary: I infused the syrup with a sprig of rosemary for some extra depth of flavor. Rosemary and olive oil are such a lovely combination! Some sugared rosemary stems as the plum leaves are the perfect festive touch.
- Granulated sugar: You'll need some granulated sugar for the cookie dough, syrup, and for coating the sugar plum cookies.
- Blue and purple food coloring: Gel food coloring gives the best results because you need a very pigmented food coloring to make sure that the color shows up.
- Plums: Fresh or frozen purple plums will work great for this recipe. Any time of plum will work well, but Italian plums work the best since they have a more vibrant "plum" flavor.
- Lemon juice: Brightens the plum flavor and also helps the plum jam set.
- Cinnamon stick and cardamom pods: I add this to the plum jam to infuse it with a subtle spiced flavor. It gives it a beautiful subtle fragrant flavor without overwhelming the plum flavor.
👩🍳 How to make sugar plum cookies
Spiced plum jam step by step

Step 1: Combine all of the plum jam ingredients in a medium saucepan. Heat on medium-low heat, stirring frequently, until it comes to a simmer.

Step 2: Cook until the jam thickens. Remove the jam from the heat and carefully remove the spices with a spoon and discard them.

Step 3: Transfer the jam to a heat safe non-metal container like a glass container and let it cool. You can make the jam a few days ahead of time and refrigerate until you're ready to fill the cookies.
Olive oil cookies step by step

Step 1: In a large bowl or stand mixer, combine sugar, salt, and eggs. Whisk until thick, creamy, and lightened in color, for about 5 minutes.

Step 2: Add oil, milk, vanilla extract and mix to combine.

Step 3: Sift the flour and baking soda into the bowl. Fold the cookie dough with a spatula until it forms a soft cookie dough.

Step 4: Cover and refrigerate the cookie dough for 1-2 hours to give the flour time to hydrate.
When you're ready to start baking, preheat the oven to 355°F (180°C) and line a cookie sheet with parchment paper.

Step 5: Use a 1 to 1 ½ tablespoon scoop to portion the cookie dough.

Step 6: Wet your hands to prevent sticking. Roll the portioned cookie dough into smooth balls. Make them slightly elongated like plums.

Step 7: Place the cookie dough balls onto a parchment lined baking sheet, leaving about 2 inches of space in between each cookie because they will rise and puff out. Bake for 11-12 minutes. The cookies are ready when the bottoms are golden brown. Don't under bake the cookies or else they will disintegrate during assembly.

Step 8: When the baked cookies are cool enough to touch, use a small sharp knife to cut the centers out of the cookies from the bottom.

Step 9: Fill each hollowed out center with a teaspoon of jam, match up the cookie halves and connect them together to form a whole plum shape.
Syrup step by step
Step 1: Combine 1 cup of granulated sugar, water, and vanilla extract in a medium saucepan.
Step 2: Heat to dissolve the sugar. Remove it from the heat and let it cool so that it's cool enough to handle.
Tip: use gloves to prevent coloring your fingers.
Step 1: Divide the syrup in half between two bowls. Color one bowl with syrup a vibrant purple color and the other bowl a vibrant blue color. You will need a lot more food coloring than you think in order for the color to translate to the cookies when you dip them in. Test a piece of cookie to see if it takes the color and this will let you know if you need more food coloring.

Step 2: Very quickly, dip half of each filled plum cookie in the purple syrup. Turn the cookie and quickly dip the undipped half into the blue syrup.

Step 3: Roll the dipped cookies into granulated sugar and set aside on a plate while you dip and roll the rest of the cookies. Repeat with the rest of the cookies.

Step 4: Add sugared rosemary sprigs to the sugared plums.
✔️ Expert cookie tips
- Let the cookie dough chill: Chilling the cookie dough for at least an hour helps hydrate the flour and makes the dough easier to work with.
- Bake the cookies just enough: Make sure you set a timer while you bake the cookies and keep a close eye on them! They need to be firm enough to hold their shape as they're dipped in syrup, and soft enough to be able to carve out the bottoms.
- Don't over-soak the cookies with syrup: A brief dunk into the syrup; in and out, is all the cookies need. If you dunk them in the syrup longer, you risk the cookies getting soggy and falling apart.
🥄 Make ahead and storage
These Italian lemon cookies are great to make ahead! Here's a break down of how you can make ahead each component:
- Olive oil cookie dough: This can be made the day before. Cover the bowl of cookie dough tightly so that the top doesn't dry out and store in the fridge for up to 24 hours
- Baked lemon olive oil cookies: If you want to bake the cookies ahead of time and fill them later, they store well in an airtight container or bag at room temperature for up to 2 days.
- Cookie syrup: The syrup can be made a few days ahead of time. Store the syrup in an airtight jar or container in the fridge. Then when you're ready, you can divide the syrup between two bowls, add food coloring, and dip the cookies.
The fully assembled, filled and dipped sugar plum cookies store really well! Keep them in a single layer so that they don't stick together. Store in an airtight container or cover the tray tightly with wrap to prevent them from drying out. The cookies will stay soft and moist, refrigerated, for up to 5 days.
If making these for an event, it's best to fill and dip the cookies the day before and store them in the fridge until you're ready to serve them. They taste especially delicious after they have the chance to soak through overnight. These sugar plum cookies do well at room temperature for a long time, so they're great for cookie boxes where the cookies can sit out for more than a few hours.

❔ What else can I fill sugar plum cookies with?
You can fill these cookies with any kind of jam that you like! Apricot, blueberry, raspberry... Alternatively, fill the centers of the cookies with dulce de leche like my walnut cookies or even a chocolate hazelnut spread.
You can also fill them with blueberry curd or even raspberry curd! Or try my Italian lemon cookies which is the lemon version of these sugar plums.

📖 Recipe FAQs
I haven't tried it, but replacing the flour with 1:1 gluten free flour should work well. If you try it out, let us know how it went in the comments!
Yes you can fill them with a thick custard, your favorite jam, dulce de leche, or caramel. Anything that's thick and sticky to hold the cookies together will work well.
Extra virgin olive oil gives these cookies a delicious subtle earthy flavor that pairs beautifully with the plum jam. If you don't like the flavor of olive oil, you can use a light olive oil or a different, more neutral flavored oil like vegetable oil, canola oil, or grapeseed oil.
🎄 More related recipes
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📖 Recipe
Sugar Plum Cookies
Equipment
Ingredients
Spiced Plum Jam
- 2 cups plums pitted and cut into cubes
- 1 cup granulated sugar
- 1 teaspoon pure vanilla extract
- 2 tablespoon lemon juice
- 2 inch piece cinnamon stick
- 3 cardamom pods
Cookie dough
- 1 cup granulated sugar
- ¼ teaspoon sea salt
- 2 large eggs room temperature
- ½ cup extra virgin olive oil or neutral oil
- 3 tablespoons milk whole milk or your preferred milk
- 1 tablespoon pure vanilla extract
- 3 cups all purpose flour 360g
- 2 teaspoons baking powder
Syrup
- 1 cup granulated sugar
- 2 cups water
- 1 teaspoon pure vanilla extract
- 2 inch rosemary sprig
- blue food coloring as needed
- purple food coloring as needed
- ½ cup granulated sugar for coating
- Sugared rosemary sprigs for decorating
Instructions
Spiced plum jam
- Combine all of the plum jam ingredients in a medium saucepan. Heat on medium-low heat, stirring frequently, until it comes to a simmer.2 cups plums, 1 cup granulated sugar, 1 teaspoon pure vanilla extract, 2 tablespoon lemon juice, 2 inch piece cinnamon stick, 3 cardamom pods
- Cook until the jam thickens. Remove the jam from the heat and carefully remove the spices with a spoon and discard them.
- Transfer the jam to a heat safe non-metal container like a glass container and let it cool. You can make the jam a few days ahead of time and refrigerate until you're ready to fill the cookies.
Cookie dough
- In a large bowl or stand mixer, combine sugar, salt, and eggs. Mix until thick, creamy, and lightened in color, for about 5 minutes.1 cup granulated sugar, ¼ teaspoon sea salt, 2 large eggs
- Add oil, milk, vanilla extract and mix to combine.½ cup extra virgin olive oil, 3 tablespoons milk, 1 tablespoon pure vanilla extract
- Sift the flour and baking powder into the bowl. Fold the cookie dough with a spatula until it forms a soft cookie dough.3 cups all purpose flour, 2 teaspoons baking powder
- Cover and refrigerate the cookie dough for 1-2 hours to give the flour time to hydrate.
- When you're ready to start baking, preheat the oven to 355°F (180°C) and line a cookie sheet with parchment paper.
- Use a 1 or 1 ½ tablespoon scoop to portion the cookie dough into cookies.
- Wet your hands to prevent sticking. Roll the portioned cookie dough into smooth balls. Try to make them slightly elongated like plums.
- Place the cookie dough balls onto a parchment lined baking sheet, leaving about 2 inches of space in between each cookie because they will rise and puff out. Bake for 11-12 minutes. The cookies are ready when the bottoms are golden brown. Don't under bake the cookies or else they will disintegrate during assembly.
- When the baked cookies are cool enough to touch, use a small sharp knife to cut the centers out of the cookies from the bottom.
- Fill each hollowed out center with a teaspoon of jam, match up the cookie halves and connect them together to form a whole plum shape.
Syrup
- Combine 1 cup of granulated sugar, water, vanilla extract, and one rosemary sprig in a medium saucepan.1 cup granulated sugar, 2 cups water, 1 teaspoon pure vanilla extract, 2 inch rosemary sprig
- Heat to dissolve the sugar. Remove it from the heat and let it cool so that it's cool enough to handle.
- Divide the syrup in half between two bowls. Color one bowl with syrup a vibrant purple color and the other bowl a vibrant blue color. You will need a lot more food coloring than you think in order for the color to translate to the cookies when you dip them in. Test a piece of cookie to see if it takes the color and this will let you know if you need more food coloring.blue food coloring, purple food coloring
- Tip: use gloves to prevent coloring your fingers. Very quickly, dip half of each filled plum cookie in the purple syrup. Turn the cookie and quickly dip the undipped half into the blue syrup. Roll the dipped cookies into granulated sugar and set aside on a plate while you dip and roll the rest of the cookies.½ cup granulated sugar
- Add sugared rosemary sprigs for the leaves and stems.Sugared rosemary sprigs




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