Chronic wounds significantly burden healthcare systems worldwide, requiring novel strategies to ease their impact. Many physiological processes underlying wound healing are well studied but the role of mast cells is controversial. Mast cells are innate immune cells and play an essential role in barrier function by inducing inflammation to defend the host against chemical irritants, infections, etc. Many mast cell-derived mediators have proposed roles in wound healing; however, in vivo evidence using mouse models has produced conflicting results. Recently, studies involving more complex wound models such as infected wounds, diabetic wounds and wounds healing under psychological stress, suggest that mast cells play critical roles in these processes. This review briefly summarizes the existing literature regarding mast cells in normal wounds and potential reasons for the contradictory results. A focus will be placed on examining more recent work emerging in the last 5 years exploring mast cells in more complex systems of wound healing including infection, psychological stress and diabetes with a discussion of how these discoveries may inspire future work in the field.