If one executes the following in a graphical frame, the line will break: (insert (propertize "\n" 'display `(space :align-to (- right)) 'face '(:underline t)) "\n") (toggle-word-wrap 1) If one makes the line one pixel shorter, it will work fine. (insert (propertize "\n" 'display `(space :align-to (- right (1))) 'face '(:underline t)) "\n") (toggle-word-wrap 1) Evgeni