At the moment, there are some problems with regard to bundler + did_you_mean because of did_you_mean being a bundled gem. Since the vendored version of thor inside bundler and ruby itself explicitly requires did_you_mean, it can become difficult to load it when using Bundler.setup. See this issue: https://github.com/yuki24/did_you_mean/issues/117#issuecomment-482733159 for more details.