The HP Tilt Pen MPP 2.0 is not specifically designed for the Dell Latitude 5290. It is compatible with devices that support the Microsoft Pen Protocol (MPP) 2.0, which is typically the case with HP devices. Since the Dell Latitude 5290 is not explicitly mentioned as a compatible device for this pen, it may not work fully. However, the pen works fine on your Microsoft Surface Pro, which indicates that the issue is more likely related to compatibility with the Dell Latitude 5290.