I found this out from a related issue on jekyll's repo: This does break listening on shared folders though but the old behavior can be forced using the -force_polling option along with -watch when using build or serve: jekyll serve -watch -force_polling Jekyll up to version 1.2.1 would poll directories for changes by default, but it has since changed the way it listens for modifications, apparently to use inotify events, which works better. VirtualBox will not send inotify events for shared folders to the guest. There is no need to install an older version of jekyll - you need to use -force_polling.
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