For individual sized challah-tashen, divide your dough into 3 ounce portions (I like to do this before my dough rises for the first time). For large challah-tashen, divide dough into 24 ounce (1 ½ pound) portions. A 5 pound batch of dough should give you about 6 large portions or 48 individual portions.
Form each piece of dough into a ball and place on parchment-lined baking sheets. Spray tops and sides with cooking spray and cover tray with plastic wrap. Place a clean kitchen towel over the top (this keeps the heat in and helps the dough to rise) and allow dough to rise for about 2 hours (less if your kitchen is warm, more if it’s on the colder side) or until doubled in size. (Note that egg-free recipes tend to rise much faster, and are often stickier than egg doughs. Adjust your rising time or flour as necessary to make sure your dough is easy to work with. If it’s too sticky it may be harder to fill and shape. I also do not like to flour my work surface, as the dough will not pinch together well, and you may end up losing your fillings. I prefer to gently oil my hands as necessary if the dough is a little too sticky.)
Preheat oven to 350°F. Line additional baking sheets with parchment paper. Place one piece of dough onto a clean work surface, and using the palm of your hand, gently flatten dough into a about a 6-inch circle (for the larger dough, I use a rolling pin, and roll into about a 15-inch circle). Your flattened dough should be about a ½ inch thick. For small sized dough, place roughly 2-3 tablespoons of your desired filling into the center of your flattened dough circle, leaving about a 1-inch border. (Use your judgement when it comes to the amount of filling. You want a nice dough to filling ratio, but if you overfill your dough, it will split and seep out.)
Fold the dough up on 2 sides and pinch to form one corner. Fold up the third side and pinch additional 2 corners to form a triangle (just like you would a traditional hamantash). Continue pinching all 3 corners all the way up to the center to seal filling in completely. Once tightly sealed, carefully flip your dough over so the sealed side is face down. Feel free to manipulate dough as needed to form a neat triangle.
Repeat with remaining dough and place on prepared baking sheets. Be sure to leave enough space for dough to rise (I can usually fit about 10 small or 2 large doughs per baking sheet). Cover challahs once more with a kitchen towel and allow to rise an additional 45 minutes to an hour (depending on the heat of your kitchen – again, they should double in size).
Brush each challah with egg wash and sprinkle with suggested toppings (ideas below). Bake small challah-tashen for 22-30 minutes and large for 35-45 minutes (this may vary depending on which filling/topping you are using – crumb toppings may take slightly longer to bake), or until browned on top and edges. Rotate your pans ⅔ of the way through baking. Transfer to baking racks to cool. Enjoy as an appetizer, accompaniment or even as dessert!
Recipe by Between Carpools at https://betweencarpools.com/new-must-make-purim-challah-taschen/