It has recently been argued that high-confidence eyewitness identifications are highly likely to be accurate regardless of the quality of viewing conditions experienced by the witness. However, new evidence suggests that evaluators of eyewitness identification evidence (e.g., jurors) do not trust highly confident eyewitnesses who experienced poor witnessing conditions. In fact, contextual information about poor witnessing conditions decreases evaluators’ belief of eyewitnesses to a greater extent for highly confident witnesses than for moderately confident witnesses. Why is the effect of witnessing-condition information greater for evaluations of high-confidence witnesses than for less confident witnesses? The current research tested the possibility that information about witnessing conditions influences evaluators’ perceptions of how well-calibrated a witness’s identification confidence is with the eyewitness’s accuracy. Using a paradigm adapted from the confidence calibration literature, I conducted an experiment to test this calibration account of the finding that witnessing condition information has a stronger effect on perceptions of highly confident witnesses than moderately confident witnesses. Although the results replicated the differential effects of witnessing condition context on perceptions of highly and moderately confident eyewitnesses, they failed to yield support for the confidence calibration hypothesis, potentially because the confidence calibration manipulation was ineffective. Directions for future research are discussed.