Color smudge operations from digital painting software enable users to create natural shading effects in high-fidelity paintings by interactively mixing colors. To precisely control results in traditional painting software, users tend to organize flat-filled color regions in multiple layers and smudge them to generate different color gradients. However, the requirement to carefully deal with regions makes the smudging process time-consuming and laborious, especially for non-professional users. This motivates us to investigate how to infer user-desired smudging effects when users smudge over regions in a single layer. To investigate improving color smudge performance, we first conduct a formative study. Following the findings of this study, we design SmartSmudge, a novel smudge tool that offers users dynamical smudge brushes and real-time region selection for easily generating natural and efficient shading effects. We demonstrate the efficiency and effectiveness of the proposed tool via a user study and quantitative analysis.