Heat olive oil in a large cast-iron skillet over medium-high heat. Season chicken pieces generously with salt and pepper, then sear them for 4-5 minutes per side until golden brown. Remove chicken to a plate and set aside temporarily while you build your sauce base.
In the same skillet, melt butter and sauté diced onion for 2-3 minutes until softened and fragrant. Add minced garlic and cook just 1 minute more, stirring constantly to prevent burning while releasing those precious aromatic oils.
Stir in pumpkin puree, chicken broth, dried sage, thyme, and paprika, mixing thoroughly to combine. This cozy fall skillet chicken pumpkin recipe begins truly taking shape as the sauce develops its signature creamy texture and warming spice profile.
Return seared chicken to the skillet, nestling pieces into the sauce. Reduce heat to medium and simmer uncovered for 15 minutes, allowing flavors to meld while chicken cooks completely through to an internal temperature of 165°F.
Stir in fresh spinach and heavy cream, cooking just 2-3 minutes more until greens wilt completely. Taste the dish and adjust seasonings with additional salt, pepper, or sage as needed for your preference.