Bring a large pot of water to boil. Using a paring knife, carefully score a shallow X shape on the bottom of each tomato. Prepare a large bowl of ice water.

Once the water is boiling, work in batches to poach the tomatoes for 60-90 seconds, or until the skin splits up the sides. Transfer to the bowl of ice water to stop the cooking. Repeat with the remaining tomatoes.

When cooled, use your hands or a paring knife to peel the tomatoes  and discard the skins and core. Slice the tomatoes in half and squeeze the juice and seeds into a bowl and discard. Roughly chop the tomatoes and set aside.

Roast the bell peppers over a flame until they are entirely charred. Transfer them to a bowl, and cover tightly with plastic wrap for 10-15 minutes.

Once the peppers are cool enough to handle, use your hands or a paring knife to peel off the charred skin and remove the seeds. Dice the peppers.

Add the tomatoes, peppers, garlic cloves, and oil to a large pot. Bring the mixture to a boil, then reduce the heat to low. Simmer for 30 minutes, stirring occasionally. 

After the mixture softens into a sauce-like consistency, add the paprika(s) and 1 ½ teaspoon of kosher salt. Continue to slowly simmer the matbucha until it reduces to about half the volume, and it becomes a jammy texture, about 1 hour and 15 to 1 hour and 30 minutes.

Cool slightly, then taste and adjust salt if needed. Serve with fresh challah.