Through the application of mechanochemistry, we developed a new approach for the synthesis of indolone-based photoswitches (hemiindigos, hemithioindigos, and oxindoles) via Knoevenagel condensation reactions. The use of a liquid base (piperidine) ensures LAG conditions for a better homogenization of the reagents. Furthermore, the simplicity of the method enables its applicability for a wide scope of reagents, offering a highly stereoselective synthesis of small molecules and large macrocyclic structures. By these means, new unreported photoswitches could be obtained in moderate to high yields. For the new derivatives, the detailed studi es of the photoswitching processes and their structure-properties relationships, as well as their further applications, are in progress.