Prepare your chicken by sprinkling salt and pepper on each cutlet. Wrap each cutlet with one slice of prosciutto.
Select the saute function on the Instant Pot. After 2-3 minutes and once the pan is hot, coat the pan with 1 tbsp oil. Place each cutlet in the pot, and cook for 2-3 minutes per side or until each cutlet is slightly crispy. Set aside.
Add the remaining tbsp of oil, the saute the garlic and shallot for 1-2 minutes. Select cancel on the Instant Pot.
Pour in the wine and deglaze the bottom of the pot by scraping the browned bits with a spatula (this helps to prevent burning later). Stir in dijon mustard, and place the dates in the pot. Nestle the chicken on top of the dates. Secure the lid on the IP.
Select manual or high pressure, and cook on high pressure for 5 minutes. Use a quick release when cook time is complete. Release all steam before opening the lid.
Remove the chicken to a plate. Select cancel, then saute. Stir the arrowroot with 1 tbsp of water, and transfer to the wine sauce. Cook for another 2-3 minutes, or until the sauce thickens.
Serve hot by pouring sauce over each cutlet and topping with fresh herb of choice. Salt and pepper to taste.
*Use a dry white wine like chardonnay or sauvignon blanc. For a Whole30 variation, use 1 cup chicken broth and 3 tbsp of white wine vinegar.