A novel palladium(II)-catalyzed intramolecular [2 + 2 + 2] annulation of indolyl 1,3-diynes is described in this contribution. A variety of azepino-fused carbazoles are obtained in moderate to excellent yields. The key to the success of this transformation is the use of a carboxylic acid as an additive. This protocol features broad functional group tolerances, easy handling in air, and 100% atom economy. Furthermore, scale-up reactions, late-stage derivatizations, and photophysical property investigations highlight the potential synthetic utility of this methodology.