The main objectives of this dissertation are: to research the theatrical term “artistic director”; and to investigate how an artistic director of a theatre troupe performs as an “auteur in contexts”. Through the case study of Dr. Joanna Chan (Chan), the second-ever artistic director of the Hong Kong Repertory Theatre (“the Rep / HKRep” / the Theatre), this dissertation examines the execution of her artistic directorship while she worked for a theatre company established and operated by the British colonial government. Auteur theories, Andrew Sarris’ in particular, are applied to investigate Chan’s creative works. “Artistic director” is a relatively new term in drama history. No serious or special studies have been conducted on the position, despite the fact that the job-holder is the creative force of a theatre company – by no means a meagre role. This dissertation closely studies the artistic directorship of Chan as an “auteur in contexts” when she took up the position at HKRep during Hong Kong’s final decade under British rule, particularly after the Sino-British Joint Declaration had been signed. Taking advantage of special political and social contexts, and as a Catholic nun with a broadly exposed, overseas educational background and an established career in theatre, Chan created local discourses in Hong Kong as an “auteur in contexts” by writing original plays and setting up the Rep’s first-ever theme for its drama season – Facing Deadlines. The bold and unique offerings of the drama season she designed, along with her other artistic works, all explored individuals’ dilemmas, social anxieties, and the Hong Kong people’s conflicting identity, induced by “the 1997 deadline”. Her emphasis on writing and promoting original plays had greatly contributed to the shift in the Rep’s programming from purely artistic offerings to productions tinted with social agendas. Through first-hand information obtained by interviewing Chan, other industry insiders and drama critics; through close study of Chan’s plays for textual analyses; and through research carried out particularly in the Rep’s news clippings library, this case study investigates how Chan as an artistic director managed to carve out a space for herself, to display her own style as an “auteur in contexts” of the text of HKRep, and to influence the local drama scene while working under a system replete with governmental constraints as well as facing larger political, social and cultural changes in society