Remember to cover the basics, that is, what you expected to happen and what in fact did happen. You don't know how to make a good report? See https://orgmode.org/manual/Feedback.html#Feedback Your bug report will be posted to the Org mailing list. ------------------------------------------------------------------------ I have noticed that some of my drill entries are skipped by org-drill, and only recently took the time to try to troubleshoot why – apparently org-drill-entry-empty-p returns t for my entries, because they look like the following: ----- * Entry question? :drill: SCHEDULED: <2019-04-05 Fri> :PROPERTIES: ... :END: ** The Answer Some text ---- Since org-drill-entry-empty-p only looks from the end of the metadata/properties and until outline-next-heading, it will consider this drill entry empty – even though this is not at all my intention. This would be fixed by replacing (outline-next-heading) with (outline-forward-same-level 1) in org-entry-empty-p. I'm not sure whether this has any other adverse effect, but I can't see how it would make things worse, at least. Emacs : GNU Emacs 26.2 (build 1, x86_64-apple-darwin18.6.0, Carbon Version 158 AppKit 1671.5) of 2019-06-15 Package: Org mode version 9.1.6 (9.1.6-48-gfe7619-elpaplus @ /Users/christoffer/.emacs.d/elpa/org-plus-contrib-20180212/)