The phase behavior of the binary system consisting of the commercial nucleating and clarifying agent 1,3:2,4-bis(3,4-dimethyldibenzylidene)sorbitol (DMDBS, Millad 3988) and isotactic polypropylene (i-PP) was investigated over the entire concentration range by means of differential scanning calorimetry (DSC), rheology, and optical microscopy. Experimental phase diagrams were constructed from data obtained in melting and crystallization studies, and a simple binary monotectic is advanced. Distinct regimes in the phase diagram, which apparently dictate nucleation and clarification of i-PP by DMDBS, are discussed. A maximum increase in the crystallization temperature of i-PP due to the nucleating action of DMDBS was observed in compositions containing between 0.2 and 1 wt % of the latter. Liquid-liquid phase separation was observed at elevated temperatures for i-PP/DMDBS mixtures comprising more than 2 wt % of DMDBS. A study of the optical properties of the i-PP/DMDBS system revealed that values for haze and clarity of injection-molded plaques progressively decreased and increased, respectively, in the concentration range between 0.2 and 1 wt % DMDBS in i-PP; at DMDBS concentrations exceeding 1 wt % the presence of the additive had an adverse effect on the optical properties of i-PP. Finally, a surprisingly strong influence of cooling kinetics on the phase behavior and, consequently, on the optical properties of the i-PP/DMDBS system was detected, which is of obvious relevance for industrial applications.