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Expert secondary Arts teachers are highly trained specialists well versed in face-to-face individual and group teaching pedagogies. Given the highly personalised nature of Arts teaching practice, the shift to online teaching resulting from COVID-19 lockdowns presented many with challenges for which they had little or no formal training. Many teachers felt stressed, isolated and unsure about where to turn for help. As there are demonstrated links between stress and attrition, it is important to reflect upon the experiences of these teachers with the aim of developing future mitigation strategies. The research reported here synthesises the online teaching experiences of 15 expert Arts specialists in Western Australia and revealed that being a digital native was not in itself sufficient to ameliorate online teaching challenges. Rather, the study found that teachers with deep pedagogical practice knowledge and a reflexive/flexible approach fared better than those with high levels of technology familiarity. The importance of collegiality and mentoring in an online setting, along with a reappraisal of teaching priorities emerged as key findings and serve as a timely reminder of the importance of collaboration, especially in testing times.