Thanks! I'd looked at that menu, seeing if I could add flags to R CMD check that would cause it to generate docs. Somehow I completely skipped the "generate documentation with Roxygen" section
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With this option set, when Cmd + Shift + E on my IDE, it runs devtools::check() which has a default to document = TRUE .
Yep, when I Cmd + Shift + E without "generate documentation..." checked, it runs devtools::check(document = FALSE), which I believe is RStudio's default.
I'm still curious why RStudio's default differs from devtools::check's default. Is it just to provide consistency with the base R CMD check by default?