Little is known in Australia as to whether the types of jobs that disadvantaged jobseekers are encouraged to enter do actually provide the basis for a ‘successful’ transition into the labour market. At the very least, this ‘successful’ transition would consist of being able to retain employment. Ideally, it would then lead to career advancement and wage progression. This study outlines the support provided by existing employment assistance programs to enable disadvantaged job seekers to make such a transition, then uses the Household Income and Labour Dynamics in Australia (HILDA) survey to examine the extent to which low-skilled jobseekers both retain employment and then advance. Aggregate figures highlight problems with jobseekers retaining employment with at least circumstantial evidence of a ‘low-pay no-pay’ cycle in the Australian labour market. We conclude that to improve employment retention and advancement of the low-skilled, current employment assistance programs should be expanded to include a range of retention and advancement strategies that have been developed in the US and the UK.