BACKGROUND: Older adults may have difficulties in using everyday technologies, ET, e.g. micros, computers, particularly those with cognitive impairment. To guide supportive interventions, more knowledge of how to best assess ET use is needed. OBJECTIVE: To provide new knowledge of perceived and observed levels of difficulty of ETs in older adults with and without cognitive impairment. METHODS: Two samples of older adults (n = 118 and 116) with and without cognitive impairment were assessed. One was interviewed with the Everyday Technology Use Questionnaire (ETUQ) about perceived difficulties in ET use. The other sample's observed ability to manage ET was assessed with the Management of Everyday Technology (META). Data was analyzed using a Rasch measurement model and rank-ordered hierarchies of perceived and observed levels of ET difficulty were identified, correlated and examined. RESULTS: Findings demonstrated a correlation of 0.63 (p < 0.001). The upper range of both hierarchies contained more complex ETs like cell phones and computers while the lower comprised more home maintenance ETs. CONCLUSIONS: Perceived and observed levels of ET difficulty appear as similar, yet not identical constructs. In self-reports, though, ETUQ to a great extent seems to capture levels of ET difficulty. However, in clinical practice observations of actions may guide interventions, as they can identify why an ET is difficult.