Aircraft accidents and incidents associated with visual flight into instrument weather conditions continue to account for a significant proportion of fatalities involving general aviation aircraft. The aim of this study was to examine pilot recounts of flights involving inadvertent or deliberate flight into Instrument Meteorological Conditions (IMC). Of the 251 responses that were examined, 145 pilots indicated that they had entered IMC inadvertently during a visual flight, while 93 had done so deliberately. Amongst non-instrument-rated pilots, two cohorts were identified whereby pilots who deliberately entered instrument conditions tended to have experienced the conditions previously, possess a comparatively greater tolerance of risk, experienced less anxiety during the event recounted, and perceive the risks associated with the transition into instrument conditions as relatively lower than those pilots whose entry into instrument conditions was inadvertent. These results are interpreted as confirmation of the need to address the problem of visual flight into instrument conditions from a number of different perspectives, taking into account experience and individual differences in risk tolerance.