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Per NickD's comment this may well be a bug. In the meantime, it looks like this does what you're aiming for (or at least points you in the right direction): (defun dunne//add-deadline-warning (w) (save-excursion (org-back-to-heading t) (let* ((regexp org-deadline-time-regexp)) (if (not (re-search-forward regexp (line-end-position 2) t)) ...


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