It is a Phd dissertation, which all the 5 chapters are attempted, however, my supervisor still have comments on my work, so i need to rectify according to the comments. This project examines the critical success factors contributing to success of telework as a work practice_when it is applied in the business-to-consumer electronic business context_ Research into telework critical success factors in the e-business environment is justified by the absence of models or theories that examine telework in that environment, and by the lack of investigation into the success factor. The project aims to identify what factors are at play in the successful deployment of telework in the e-business environment especially in the business to consumer type. Qualitative research methods was used to collect data through in-depth interviews from multiple cases allowing triangulation to occur. Four pilot interviews were conducted along with some in- depth interview for primary data collection , with teleworkers conducting e-business operations in Singapore. Two types organisations were chosen one is Singaporean owned insurance companies located in Singapore and the the other an American–owned insurance companies located in Singapore.