Robotic approaches have facilitated the minimally invasive completion of increasingly complex surgical procedures. In the management of the difficult gallbladder, we have found that the wristed instruments, three-dimensional camera, the ability to use indocyanine green (ICG) with integrated fluorescent imaging, and ease of intracorporeal suturing to be useful in tackling the challenges associated with complex benign gallbladder disease. We describe the rationale and technical lessons learned during four cases of complex cholecystectomies that highlight the management principles and technical advantages afforded by the use of the robotic-assisted laparoscopic (RAL) approach. The cases include a subtotal fundus-first reconstituting cholecystectomy, subtotal fenestrating cholecystectomy, a cholecystocolonic fistula managed by a RAL subtotal fenestrating cholecystectomy, and an iatrogenic cholecystoduodenal fistula managed by RAL cholecystectomy. In each case, the operation was performed safely without intraoperative injury or conversion to open, and three of the four patients were discharged from the recovery room. In our view, these favorable outcomes were greatly facilitated by the robotic platform. It is our intent to share adaptations and innovations that we found helpful to encourage other surgeons with sufficient robotic experience to tackle complex gallbladder cases minimally invasively.