For four decades, theories of job demand-control have proposed that higher occupational status groups have lower health risks due to the stress accompanying jobs featuring high demands but high control. This research examines whether Flexible Work Arrangements (FWAs) can improve the health prospects of a range of workers by giving greater control over work time arrangements. Our setting is Australia, where FWAs were introduced in 2009. In line with these early studies alongside studies of work-life balance, we expected to observe that workers with access to control over daily work times could better control the activities outside of work that influence chronic disease. Using a practice sociology approach, we compared the accounts of twenty-eight workers in blue and white collar industries with differing degrees of work time flexibility. The findings do not contradict early theories describing occupational differences of job demand-control dynamics and their relationship to health risks. However, this study suggests that a) time demands and strains have increased for a broad sweep of workers since the 1980s, b) the greater control of higher occupational status groups has been eroded by the high performance movement, which has attracted less scrutiny than FWAs, and c) more workers are forced to adapt their daily lives, including their approach to health, to accommodate their job demands. Job insecurity further impedes preventative health practices adoption. What might appear to be worker-controlled flexibility can-under the pressures of job insecurity and performance expectations without time limits-transform into health-eroding unpredictability. The answer however is not greater flexibility in the absence of limits on the well-documented precursors of work stress: long hours, job insecurity and intensity-related exhaustion. While there have been welcome developments in job demand-control-health conceptualizations, they typically ignore the out-of-work temporal demands that workers face and which compound on-the-job demands. Redesign of the temporalities of working life within worksites need to be accompanied by society-level policies which address caring responsibilities, gender equality as well as broad labour market conditions.