Introducing double bonds into chemical compounds - through vinylation, allylation, or olefination - is a fundamental strategy in organic synthesis, providing reactive handles for further functionalization such as epoxidation, dihydroxylation, metathesis, or radical reactions. Although these transformations are well-established in conventional solution-based chemistry, the introduction of C(sp²)=C(sp²) bonds remains underdeveloped under solvent-free conditions… …at least until our double bond agent took on the mission. We demonstrate how these key transformations can be performed under mechanochemical conditions, focusing on three reactions: the Tsuji-Trost allylation, the Wittig olefination, and the Heck coupling under direct mechanocatalysis. Beyond eliminating solvents, these protocols offer notable advantages: reaction times as short as 30 seconds (Wittig olefination), drastically reduced catalyst loadings (0.5 mol% Pd for the Tsuji-Trost allylation), and efficient catalyst recovery - using a palladium milling ball as the active catalyst in the Heck reaction. Along the way, we tackled what should be close to impossible: the olefination of sugars under neat conditions. Given their low open-chain content, sugars are typically poor substrates for olefination without solvent. The fact that this reaction proceeds cleanly under ball milling conditions challenges conventional expectations in dry-state synthesis. Finally, we highlight the applicability of these methods to pharmaceutically relevant compounds, demonstrating their practical value beyond proof-of-concept.