This chapter explores the issues and challenges faced in establishing trust among individuals and teams participating in offshore outsourcing of software development projects. While technical and project management aspects have been recognized as important for the success of offshore software outsourcing, the issue of establishing trust among the participants has not received specific recognition. The chapter discusses the special characteristics of offshore software outsourcing relationships which make the establishment of trust a challenge. The discussion emphasizes that a specific and planned approach of utilizing communication and coordination technology in software offshoring relationships will contribute towards trust formation. Use of communication and coordination technology in offshoring environments is recommended to be designed to increase the culture of communication, to establish a culture of transparency in communication, and to systemically maintain a trail and evidence of the communication.