We’re sorta sheepish that we so rarely turn to challah for our grilled cheese. The rich, buttery bread just sorta adds a little more panache to the everyday go-to lunch. But that’s not the biggest surprise in store with this recipe. The inclusion of a sweetly smoky homemade pastrami jam makes you feel like you’re stealthily indulging in dessert rather than lunch. And—yes, there’s more—we suspect you’ll marvel, as did we, at the trick of using mayo rather than butter to ensure a golden brown yet never burnt crust. Mic drop.–David Leite

A challah grilled cheese sandwich with pastrami jam torn in half, still connected by melted cheese.

Challah Grilled Cheese

5 / 2 votes
This challah grilled cheese is made with plenty of melty Cheddar and Gruyère cheeses and a schmear of savory pastrami jam, all nestled between slices of toasted challah.
David Leite
Servings1 servings
Calories736 kcal
Prep Time25 minutes
Cook Time1 hour 5 minutes
Total Time1 hour 30 minutes


For the pastrami jam

  • 1 tablespoon vegetable oil
  • 2 medium (12 oz) yellow onions, diced
  • 8 ounces pastrami, chopped (do NOT trim the fat!)
  • 1/2 cup packed golden brown sugar
  • 1/2 cup apple cider vinegar
  • 1/4 cup maple syrup

For the challah grilled cheese

  • Two (1/2-inch) thick slices store-bought or homemade challah
  • 2 slices Cheddar, American, or other desired cheese
  • 1 slice aged Gruyère cheese
  • 2 teaspoons mayonnaise


Make the pastrami jam

  • In a heavy-bottomed skillet over medium-high heat, warm the oil until nearly smoking, about 5 minutes.
  • Add the onions and cook, stirring often and reducing the heat to if necessary, until translucent, 5 to 6 minutes.
  • Add the pastrami, stir, and cook for 3 to 4 minutes.
  • Add the sugar, vinegar, and maple syrup and stir to combine. Bring to a simmer and cook until the liquid begins to thicken, stirring occasionally, 8 to 10 minutes.
  • Reduce the heat to medium-low and cook until the mixture is thick and dark in color, stirring every 15 minutes or so to prevent sticking and burning, 35 to 55 minutes more. Remove from the heat.
  • Using a food processor or an immersion blender, process the mixture to a jammy consistency. Transfer to an airtight container and let it cool. (You can cover and refrigerate the pastrami jam for up to 1 week or freeze it for up to 3 months. To return it to a spreadable consistency, thaw and then microwave at 50% power for 2 about minutes to warm it through.)

    ☞ TESTER TIP: You’ll have a heck of a lot more pastrami jam than you’ll need for a single grilled cheese. This is not a bad thing. Spoon what’s left on any sandwich or burger.

Make the challah grilled cheese

  • Heat a seasoned cast-iron skillet (a nonstick pan will do in a pinch) over medium heat until hot, 4 to 5 minutes.
  • Place the bread on a cutting board. Spread 1 1/2 tablespoons jam on a slice of challah. Top it with a slice of American cheese. Add the Gruyère and the second slice of the American cheese. Place the second slice of challah on top of the American cheese and spread the top with half the mayonnaise, smearing it from edge to edge.
  • Reduce the heat to medium-low. Carefully pick up the sandwich place it, mayonnaise-slathered side face down, in the center of the skillet. Cook the sandwich, undisturbed, until the cheese begins to melt, 4 to 6 minutes.

    ☞ TESTER TIP: You may need to reduce the heat to low if the bread starts turning dark too quickly.

  • While the first side cooks, carefully spread the remaining mayonnaise on the top slice of bread. Use a spatula to carefully flip the sandwich. Press down on the sandwich with the spatula and cook until the bottom is golden brown and the cheese has melted, 4 to 5 minutes more.
  • Remove the grilled cheese from the skillet and transfer to a cutting board. Cut as desired and serve ASAP.
Eat Something Cookbook

Adapted From

Eat Something

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Serving: 1 sandwichCalories: 736 kcalCarbohydrates: 73 gProtein: 32 gFat: 34 gSaturated Fat: 15 gMonounsaturated Fat: 10 gTrans Fat: 1 gCholesterol: 135 mgSodium: 1165 mgFiber: 3 gSugar: 21 g

Nutrition information is automatically calculated, so should only be used as an approximation.

Tried this recipe?Mention @leitesculinaria or tag #leitesculinaria!
Recipe © 2020 Evan Bloom | Rachel Levin. Photo © 2020 Maren Caruso. All rights reserved.

Recipe Testers’ Reviews

Three words: dessert for breakfast! I have to say that it was the pastrami jam that reeled me in at first but this grilled cheese was a perfect Saturday morning breakfast with black tea and fruit. I made the jam the night before and couldn’t wait to try this grilled cheese the following morning.

Two challah grilled cheese halves stacked on top of each other with a sprig of watercress to garnish.

In 20 minutes and with triple the ingredients, our family of  three sat silently at the table with occasional sighs and finger-licking bliss. My daughter, who deconstructs all her sandwiches, ate hers whole, crunching away at the crust and stretching the stringy filling in a trance.

My challah slices were smallish and 1 tablespoon of the jam probably would have sufficed. Although sweet, the tangy and creamy accoutrements balanced this breakfast treat! I didn’t have American cheese so I used applewood-smoked mozzarella. I think it would have taken almost the same time to make just 1 sandwich.

Being a grilled cheese lover, I would enjoy one with just about any kind of cheese. To me, the crisp and gooey contrast is the true make-or-break of a fabulous grilled cheese, and this recipe nails it. Soft and airy challah and mayonnaise make a weightless and crisp gateway to melty cheese and sticky pastrami jam inside.

A challah grilled cheese sandwich sliced in half on a grey plate.

It took a few tries though to achieve that ideal contrast. The biggest challenge was getting the aged Gruyère in the middle to completely melt without burning the challah. Two easy adjustments led to a great success: lowering the heat to low once the sandwich hit the skillet and keeping it covered the entire cooking time, which actually doesn’t make the bread soggy. The last grilled cheese was beautiful toasty brown and, when pressed, the cheeses and jam oozed out just a bit but the sandwich could still be picked up by hand and wolfed down without a mess.

My pastrami was fairly lean, and it only took 35 minutes to turn thick and jammy. Overnight refrigeration stiffened the jam, but all I had to do was warm it in the microwave (2 min at 50%) to make it spreadable again.

I used the traditional braided challah. The city I live in has one of the largest Jewish communities in the country, and Jewish food items are for the most part solidly old-school. The only other kind of challah I could find were challah rolls—no challah in a sandwich loaf form.

Um…HELLO PASTRAMI JAM! Where have you been all of my life?! I couldn’t believe how easy it was to make and how it elevated the grilled cheese to new levels.

I made this sandwich for my boyfriend as I’m trying to not eat so much cheese but it was so darn good my self discipline flew out the window and I made another. He thought that it was the right amount of jam but I wanted a bit more on my sandwich.

I ended up with 1 1/2 cups of the pastrami jam. I toasted a bagel and then spread it with some hot mustard and the jam and topped it with Swiss cheese. I put it under the broiler to melt the cheese and it was really yummy.

About David Leite

I count myself lucky to have received three James Beard Awards for my writing as well as for Leite’s Culinaria. My work has also appeared in The New York Times, Martha Stewart Living, Saveur, Bon Appétit, Gourmet, Food & Wine, Yankee, Los Angeles Times, Chicago Tribune, The Washington Post, and more.

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