We present a field study conducted in the homes of twelve older adults aged 55+, using a technology probe which was a cognitive assessment prototype, to investigate interruptions that occurred and the strategies they used for resuming the interrupted computerized home health assessment. We identified different types of interruptions relevant to older adults’ technology use at home: internally-generated interruptions, household interruptions, and exterior interruptions. We also shed light on participants’ current practices when dealing with interruptions and proposed strategies that can be used to prevent interruptions, detect them when they occur, mitigate their disruptive effects, and facilitate efficient task resumption following an interruption. Our findings have a number of implications for the design of home health assessments, as well as other home healthcare technologies used by older adults. The findings also has the potential of alleviating the strain on the increasing healthcare costs in clinical settings and allowing older adults to age in the comfort of their own home.