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
http://orgmode.org/manual/Feedback.html#Feedback Your bug report will be posted to the Org-mode mailing list. ------------------------------------------------------------------------ emacs -nw -q testfile, M-x org-mode M-x org-indent-mode Enter following plain list: - item1 - item1.1 - item2 Move to first line ("item1") and C-c * to org-toggle-heading. "item1" becomes a heading (ok), "item1.1" gets line/wrap prefix for indentation (ok), but "item2" is not affected at all. I believe the last list item should get the prefixes as well, as it belongs to the same subtree. The same thing happens in a large tree structure (ie, it does not depend on the first or the only heading being inserted). Debugging the after-change function was sketchy (sometimes it was applied in a narrowed buffer of zero length etc), but it seems that org-indent-refresh-maybe does *not* realize it has affected a headline and should work with the whole subtree. Emacs : GNU Emacs 25.1.50.1 (x86_64-pc-linux-gnu, GTK+ Version 3.18.5) of 2015-12-11 Package: Org-mode version 8.3.2 (8.3.2-51-g713fe8-elpaplus @ /home/il/.emacs.d/elpa/org-plus-contrib-20151221/)