Low adhesion of liquids on solid surfaces can be achieved with protrusions that minimize the contact area between the liquid and the solid. The wetting state where an air cushion forms under the drop is known as the Cassie-Baxter state. Surfaces where liquids form macroscopic contact angles above 150° are called superhydrophobic and superhygrophobic, if we refer to water or any liquid, respectively. The Cassie state is desirable for applications, but it is usually unstable compared to the Wenzel state, where the drop is in direct contact with the rough surface. The Cassie-to-Wenzel transition can be triggered by an increase in pressure and vibrations, but the inverse Wenzel-to-Cassie is much more difficult to observe. Here, we examine under what conditions the Wenzel-to-Cassie transition is triggered when the microscopic contact angle changes abruptly. For this, we applied a lubricant of low surface tension around drops that were in the Wenzel state on microstructured surfaces. The increase of the microscopic contact angle lifted the drop from the rough surface, when the pillar height and spacing are large and small, respectively. Numerical calculations for the drop-lubricant interface showed that the surface geometry requirements for the Wenzel-to-Cassie transition are stricter than the ones for the stability of the Cassie state. A surface geometry where the Cassie state is more stable than the Wenzel for a given Laplace pressure of the drop may not always allow the Wenzel-to-Cassie transition to take place. Therefore, the stability of the Cassie state is a necessary but insufficient condition for the inverse transition.