Prospect Theory proposed that the (dis)utility of losses is always more than gains due to a phenomena called ‘loss-aversion’, a result obtained in multiple later studies over the years. However, some researchers found reversed or no loss-aversion for affective judgments of small monetary amounts but, those findings have been argued to stem from the way gains versus losses were measured. Thus, it was not clear whether loss-aversion does not show with affective judgments for smaller magnitudes, or it is a measurement error. This paper addresses the debate concerning loss-aversion (in the prospect theoretic sense) and judgments about the intensity of gains and losses. We measured affective prospective judgments for monetary amounts using measurement scales that have been argued to be suitable for measuring loss-aversion and hence rule out any explanations regarding measurement. Both in a gambling scenario (Experiments 1 and 2) and in the context of fluctuating prices (Experiments 3a and 3b), potential losses never loomed larger than gains for low magnitudes, indicating that it is not simply a measurement error. Moreover, for the same participant, loss aversion was observable at high magnitudes. Further, we show that loss-aversion disappears even for higher monetary values, if contextually an even larger anchor is provided. The results imply that Prospect Theory’s value function is contextually dependent on magnitudes.