Chronic cloacal prolapse is a common condition in psittacine birds, particularly in cockatoos and African grey parrots (Psittacus erithacus). Techniques to permanently reduce the prolapse have been developed and include cloacal sutures, percutaneous cloacopexy, and open circumcostal or rib cloacopexy. Several complications, some of which are life-threatening, have been reported with these tissue reduction techniques. Cloacoplasty surgeries have also been advocated, but most often as an adjunct therapy. Recurrence of cloacal prolapse may occur in traditional symmetrical cloacoplasty techniques since straining pressure remains. In this case series, 5 psittacine birds (2 male and 2 female umbrella cockatoos [Cacatua alba] and 1 male African grey parrot) with chronic recurrent cloacal prolapses were treated with a novel asymmetrical cloacoplasty technique. A semicircular excision at the mucocutaneous junction from the right side with a 2-layer closure reduced the cloacal opening by 50%–75%. A tension-relieving suture was applied to aid in healing of the incision. All 5 cases had successful outcomes with no recurrent prolapses (6 months to 3 years of follow-up), except for 1 case, due to incisional dehiscence. This animal underwent a second surgical procedure that incorporated the tension-relieving suture and has not had a recurrent prolapse in over a year. This asymmetrical cloacoplasty technique provides a simple but effective method of cloacal prolapse treatment and prevention in cases of recurrent and chronic cloacal prolapses, and creates a midline physical barrier not present in symmetrical cloacoplasties. Long-term complications may include cloacolith formation or dystocia in females, and therefore reproductive management of female birds is required.