Activate the yeast. Place the warm water in a very large bowl or stand-mixer bowl. Add the yeast and about 1 tablespoon of the measured sugar. Stir and let stand 5–10 minutes, until foamy.

Add the wet ingredients. Add the remaining sugar, eggs, orange juice, and oil. Mix until combined.

Add flour and salt. Add about 9 cups of the flour plus the salt. Begin mixing on low with a dough hook or sturdy spoon.

Finish the dough. Add the remaining flour gradually only as needed. Do not force in all 10 cups if the dough already feels right.

Knead. Knead for about 8–10 minutes, until the dough is smooth, soft, elastic, and only slightly tacky.

First rise. Place the dough in a lightly oiled bowl, cover, and let rise in a warm place for 60–90 minutes, until noticeably doubled.

Mix the margarine, oil, sugar, cocoa, dry pudding mix, and egg until smooth.

The filling should be a thick, spreadable chocolate paste rather than a pourable sauce.

If it seems too loose, let it stand or chill briefly before spreading.

Divide. Punch down the risen dough and divide it into 8 equal pieces. Keep unused pieces covered.

Roll thin. Roll one piece into about a 12-inch circle, roughly 1/8 inch / 3 mm thick.

Add filling. Spread a thin, even layer of chocolate filling over the circle. Avoid piling it on too heavily.

Cut. Using a pizza cutter or sharp knife, divide the circle into 12 wedges, like a pizza.

Roll. Starting at the wide edge, roll each wedge toward the pointed tip.

Arrange. Place each rugelach point-side down on a parchment-lined baking sheet.

Repeat. Repeat with the remaining dough and filling. For slightly larger rugelach, cut each circle into 10 wedges instead of 12.

Second rise. Cover the shaped rugelach loosely and let rise for about 25–30 minutes. They should look slightly puffier but do not need to double.

Egg wash. If using, whisk the egg with 1 tablespoon water and brush the rugelach gently just before baking.

Preheat. Heat the oven to 350°F / 175°C.

Bake. Bake for about 15–18 minutes per tray, beginning to check at 15 minutes.

Check for doneness. The tops and bottoms should be lightly golden, the dough should no longer look pale or raw, and a little chocolate may bubble at the edges.

Cool. Transfer to a rack after a few minutes and cool before storing.