Based on experiment and observation, I'm 99% certain that AutoMapper does not map data annotations, at least by default. Can't find anything pertaining to this in the documentation and my searches on Stack Overflow found limited results. The most popular answer is extensions to DataAnnotationsModelMetadataProvider and DataAnnotationsModelValidatorProvider, but when I implemented the provided code, it gives me errors about duplicate "required" annotations. This is a fairly old SO answer, too, which makes me hopeful it's been improved on within AutoMapper.
Before I dig farther into the complicated (at least to me) solution, I thought I'd ask if there's something similar I'm missing. This seems like an important issue that there should be an accepted approach for, but I can't seem to find it.