In April 2006, the government of the Hong Kong Special Administration Region launched the New Dawn Project (ND). It is specifically designed as a workfare programme for single parents and child carers (mostly married women who take care of their children at home) on the Comprehensive Social Security Assistance (CSSA, a social security programme for low-income households) whose youngest children are aged 12 to 14. It aims to assist the participants to enhance their capacity for self-help, integrate into the community and move towards self-reliance through engagement in work. These CSSA recipients are required to join the ND Project to actively seek paid employment with working hours of not less than 32 per month; otherwise a penalty of HK$200 will be enforced from the CSSA payments except for those with special circumstances, such as having health problems, or additional caring responsibilities. By the end of August 2009, a total of 17,448 CSSA recipients had participated in the Project, and 5,203 of them (30%) had secured paid jobs. The Social Welfare Department had commissioned The University of Hong Kong to conduct an evaluation study in 2007, and an extension study was completed in 2009. The findings showed that the majority of the Project participants indicated that their participation in the Project had positive effect on their family income, quality of life and self-confidence. Most of them also thought that the requirement on working hours (32 hours per month) was reasonable and most parent-child relationships were not affected. Supplemented with the data collected from the study mentioned above, this paper will explore what considerations would the single parent CSSA recipients take in choosing to work or stay out of the job market beside the mandatory requirements imposed by the government. It will also situate the discussion within Hong Kong's special demography background, drastic economic restructuring, distortion of the labour market, and the limited protection of labour regulations and social security system.