Perceived job insecurity (JI) among employees is a common problem in our globalized economy that is characterized by competition and demands flexibility from both employees and employers. The existing literature presents a lot of evidence for the impact of JI on general physical health and psychological well-being outcomes, but asks for more longitudinal research on the impact of JI on specific outcomes, controlled for their baseline levels. The current study addresses this gap in existing research and investigates the associations between JI and diagnosed major depression, diagnosed acute stress, sleep quality, and the health-related behaviors of smoking and snussing in two Swedish samples from Stockholm and Norrland, over long time spans (up to 17 years for the Stockholm sub-sample). Data was obtained from the WOLF study. Results are mixed. For the Stockholm sub-sample, job insecurity correlates with most outcome measures except diagnosed stress, and predicts small shares of variance of sleep quality, the number of cigarettes participants smoke, and if participants use snus. The Norrland sub-sample replicates the impact of JI on general health and hints at a relationship between JI and sleep quality, but no other correlations with health-related behaviors or diagnoses were significant. Reasons for the differences among the sub-samples and limitations of the study are discussed.