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The dynamic nature of factors influencing teacher’s technology-related change can be overwhelming and have made it difficult to determine how real teacher change is most effectively encouraged. This paper seeks to demonstrate interaction between two, typically separated, factors: teaching beliefs and confidence using technology. The paper proposes that a general positive affect towards risk-taking in teaching affords support as teachers develop confidence and negotiate integration of technology into practice. In fact, an ‘openness to risk’ may be a precursor to sustained technology integration. This is explored through teacher case study data, from a three-year state-wide 1-to-1 laptop program, in Australia. Findings have implications for teacher and school engagement in technology-related change, as well as training and sustained support.