The Four Immeasurables Meditations (FIM) are a group of meditations rooted in Buddhism that cultivate pro-social attitudes. Previous studies have reported common difficulties during the practice of the FIM, yet there is no specific measure for those difficulties. The current study intended to develop the Difficulties during Meditation involving Immeasurable Attitudes Scale (DMIAS) to measure two aspects of common difficulties during the FIM practice: lack of concentration (LOC) and lack of pro-social attitudes (LOP). A total of 506 meditation novices were used in four studies. In study 1, exploratory factor analysis (EFA) with the data from a one-time practice of loving-kindness meditation was used to produce the 12-item DMIAS with two independent factors that were positively correlated (LOC and LOP). Studies 2, 3, and 4 validated the DMIAS in one-time practices of loving-kindness meditation, appreciative joy meditation, and compassion meditation, respectively. Across studies 2 to 4, confirmatory factor analyses supported the two-factor structure of the DMIAS, and both LOP and LOC had negative correlations with the other-focused positive emotions generated by the meditations. Although manipulations of the target to be blessed (study 3) and the length of practice (study 4) only had small impacts on the effects of meditation, the pattern of correlations between emotional outcomes and certain factors of the DMIAS was significantly different between the manipulated conditions. In summary, the DMIAS is a useful tool in understanding the difficulties during the FIM practice, and the current study also illustrated how technical details of the FIM influences the effects of the FIM practice.