Nowadays, people are faced with choices between or among alternative systems (joint evaluation, or JE mode), as opposed to evaluating only one system in isolation (separate evaluation, or SE mode). This research investigates how users make technology adoption decisions in these two contexts. Based on the context-specific theorization framework proposed by Hong et al. (2014) and integrating general evaluability theory and construal level theory, we theorize how evaluation mode (JE versus SE), as a usage context variable, interacts with other aspects of IS contexts to influence technology adoption. The IS contexts considered in this work include a user characteristic variable (construal level) and technology-related factors (perceived ease of use, PEoU, and perceived usefulness, PU). In two studies (N = 272 and N = 112), participants were presented with two new e-learning systems either in JE or SE mode. Because study (1) was conducted in two natural settings and study (2) had participants randomly assigned to manipulated evaluation modes, these two studies complement each other to offer internal and external validities. We found that in JE a higher construal level strengthened the effect of PEoU but weakened that of PU on technology adoption. These effects were reversed in SE. The findings suggest that users’ technology choices and preferences can be reversed by simply presenting the target system in different ways.