The synthesis of a bis(伪-spirocyclopropyl)silylene is reported and its reactivity revealed. Liberation of the silylene was accomplished by UV-light-mediated photolysis of a trisilane precursor. Insertion and addition reactions prove the existence and versatility of this new family of bis(伪-spirocyclopropyl)-substituted silylenes. Substitution on the flanking cyclopropyls for improved steric shielding of the reactive center remains challenging.