Begin by sterilizing your canning jars to ensure they’re ready for hot syrup. Keep the jars warm by either running them through the dishwasher or placing them in the canner with hot water. This prevents cracking when the hot syrup hits the glass.

Cut a piece of cheesecloth large enough to hold the cinnamon sticks, allspice, and cloves. Tie the cloth into a pouch, securing the spices inside. This will let the flavors infuse the syrup while keeping the spices contained. (Alternately, you can leave the cinnamon sticks whole and leave them out of the spice bags, just adding them to the pot whole if you plan on including them inside each jar, as I've done in the pictures here.)

In a large saucepan, combine the brown sugar, red wine vinegar, and pineapple juice. Add the spice bag and bring the mixture to a boil over medium-high heat, stirring occasionally to dissolve the sugar. Once boiling, reduce the heat and let it simmer uncovered for 20 minutes to allow the spices to infuse the syrup.

After 20 minutes, stir in the pineapple chunks and simmer for another 5-10 minutes, just enough for the fruit to warm through and absorb some of the syrup.

Use a slotted spoon to pack the jars with pineapple, leaving about ½ inch of space from the top. If you're cinnamon sticks to the jars, gently slip one in with the pineapple.

Ladle the hot syrup over the pineapple chunks in the jars, ensuring the fruit is fully submerged. Leave ½ inch of headspace at the top of each jar. Use a non-metallic utensil to remove any air bubbles, then adjust the syrup level if needed. Wipe the rims of the jars with a clean cloth to remove any residue that might prevent sealing. Secure the lids and tighten the bands until they are just fingertip-tight.

Carefully lower the jars into your canner, making sure they are fully covered with water. Bring the water to a boil and process the jars for 10 minutes, adjusting for altitude (see notes).

After processing, remove the canner lid and let the jars sit for 5 minutes before carefully lifting them out using jar tongs. Allow the jars to cool completely on a towel on the counter.

Once cool, check the seals by pressing on the center of the lids — they should not pop back. If the lids are sealed properly, store the jars in a cool, dark place. Your pickled pineapple will keep for up to one year. After opening, refrigerate and consume within a few weeks.