This volume presents the proceedings of the 14th International Workshop of Groupware (CRIWG 2008). The conference was held in Omaha, Nebraska, USA during September 14-18, 2008. Previous conferences were held in Argentina (Bariloche) in 2007, Spain (Medina del Campo) in 2006, Brazil (Porto de Galinhas) in 2005, Costa Rica (San Carlos) in 2004, France (Autrans) in 2003, Chile (La Serena) in 2002, Germany (Darmstadt) in 2001, Portugal (Madeira) in 2000, Mexico (Cancun) in 1999, Brazil (Buzios) in 1998, Spain (El Escorial) in 1997, Chile (Puerto Varas) in 1996, and Portugal (Lisbon) in 1995. The CRIWG workshops seek to advance theoretical, experimental, and applied te- nical knowledge of computer supported collaboration. In the CRIWG workshops, - searchers and professionals report findings, exchange experiences, and explore concepts for improving the success of people making a joint effort toward a group goal. Topics of discussion are wide ranging, encompassing all aspects of design development, depl- ment, and use of groupware. CRIWG embraces both mature works that are nearly ready for publication in peer-review journals, and new, cutting-edge works in progress. A total of 30 papers were accepted for presentation this year - 20 full papers and 10 works in progress. Papers were subjected to double-blind review by at least three members of the Program Committee.