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This multi-wave study uses the Transactional Model of Stress and Coping (TMSC) to investigate whether employees may view task changes as an organizational event that stimulates skill development or engenders job risks (i.e., qualitative job insecurity) and thereby affect employee job satisfaction. Additionally, drawing on Regulatory Focus Theory (RFT), the indirect effect of task changes on job satisfaction through these two mediators was theorized to depend on individual's regulatory focus (i.e., prevention or promotion). Mediation effects from task changes to job satisfaction via skill development and qualitative job insecurity were tested at the within-person level, while the moderating role by regulatory focus at the between-person level was tested using cross-level interactions. Results supported most of our hypotheses and also offered some unexpected insights. Task changes increased perceptions of qualitative job insecurity, which subsequently decreased job satisfaction. Although task changes did not show a significant direct link with skill development, skill development did positively predict job satisfaction six months later. We found no moderated mediation effects, however our moderator directly influenced job insecurity and skill development. Overall, the current study contributes to science and practice by providing valuable insights into the stressful processes that can evolve from task changes.