Job strain (high demands and low control) is a widely used measure of work stress. The authors introduce a new way of looking at work stress by combining job strain with job insecurity, a combination increasingly prevalent in contemporary economies, using data from a cross-sectional survey (N = 1,188) of mid-aged Australian managers and professionals. Those reporting both strain and insecurity showed markedly higher odds for mental and physical health problems (depression: odds ratio [OR] 13.88, 95% confidence interval [CI] 5.67-34.01; anxiety: OR 12.88, CI 5.12-32.39; physical health problems: OR 3.97, CI 1.72-9.16; and poor self-rated health: OR 7.12, CI 2.81-18.01). Job strain and insecurity showed synergistic associations with health, and employees experiencing both could be at heightened health risk.