On October 27, 2008, Hawaiian announced that prior to the arrival of its new A330s, it would lease two additional Airbus A330-200 aircraft, beginning in 2011, at the same time extending the leases of two Boeing 767-300ER aircraft to 2011 (to be withdrawn from service coincident with the delivery of the A330s). Two weeks later, the airline announced the lease of an additional A330-200 for delivery in the second quarter of 2010, along with negotiating for delivery of one aircraft from the earlier lease agreement to be moved up to the same quarter. In December 2010, Hawaiian ordered an additional six A330-200 aircraft, bringing the fleet total to 15. Further lease agreements were signed with Air Lease Corporation (one aircraft), and three aircraft each from Hong Kong Aviation Capital, and Jackson Square Aviation, bringing the A330-200 fleet to 22. In July 2015, Hawaiian announced the lease of an A330-200 from Air Lease Corporation. The purchase of another A330-200 was announced in December 2016.
Hawaiian began acquiring Boeing 717 aircraft for operation on the Neighbor Island network in February 2001. On June 4, 2008, the airline announced that it had agreed to lease an additional four 717 airplanes to meet demand due to the shutdown of Aloha Airlines' passenger operations and the closing of ATA Airlines, with deliveries between September and the end of 2008.
In March 2003, Hawaiian Airlines filed for Chapter 11 bankruptcy protection for the second time in its history. The airline continued its normal operations, and at the time was overdue for $4.5 million worth of payments to the pilots' pension plan. Within the company, it was suggested that the plan be terminated. As of May 2005, Hawaiian Airlines had received court approval of its reorganization plan. The company emerged from bankruptcy protection on June 2, 2005, with reduced operating costs through renegotiated contracts with its union work groups; restructured aircraft leases; and investment from RC Aviation, a unit of San Diego-based Ranch Capital, which bought a majority share in parent company Hawaiian Holdings Inc in 2004.