The ability to transport pollen from flowers back to the nest represents a key innovation in the evolution of bees from predatory wasp ancestors. Currently, the origin and evolution of pollen transport remains unsettled. Older hypotheses proposed that crop transport was the original mode of pollen transport, but more recent molecular phylogenies have cast doubt on that view. Instead, more recent hypotheses contend that external transport of dry pollen is ancestral in bees. Here, I propose a new hypothesis to explain the origin and subsequent evolution of pollen transport in bees. I propose that pollen transport arose from adult pollen-feeding behavior and that internal transport of pollen is ancestral in bees. This then led to the evolution of external moist transport, which first required a transition step whereby pollen is temporarily accumulated on the venter on a patch of specialized hairs. Finally, external glazed and dry transport evolved from external moist pollen transport, and the evolution of dry transport led to changes in the location of scopae from the original location on the hind tibia and basitarsus. I illustrate many of these hypothetical evolutionary steps using modern-day bee behavior as an example, with a particular focus on the bee Perdita tortifoliae. Examination of the evolution of pollen transport of pollen wasps (subfamily Masarinae) reveals that they have undergone a parallel evolutionary change. Overall, I lay out a broad hypothetical framework to explain the origin and subsequent evolution of pollen transport in bees. This marks a return to the earlier hypothesis that crop transport is ancestral, and it also represents the first in-depth hypothesis to explain how external transport of moistened pollen could have evolved. The evolutionary history of bees has many implications for the biology of bees in the present day, and I lay out a number of predictions that could help confirm or refute my hypotheses.