Many effective and innovative survival mechanisms used by natural organisms rely on the capacity for phenotypic plasticity; that is, the ability of a genotype to alter how it is expressed based on the current environmental conditions. Understanding the evolution of phenotypic plasticity is an important step towards understanding the origins of many types of biological complexity, as well as to meeting challenges in evolutionary computation where dynamic solutions are required. Here, we leverage the Avida Digital Evolution Platform to experimentally explore the selective pressures and evolutionary pathways that lead to phenotypic plasticity. We present evolved lineages wherein unconditional traits tend to evolve first; next, imprecise forms of phenotypic plasticity often appear before optimal forms finally evolve. We visualize the phenotypic states traversed by evolved lineages across environments with differing rates of mutations and environmental change. We see that under all conditions, populations can fail to evolve phenotypic plasticity, instead relying on mutation-based solutions.