Hi! I wrote a blog article on how I am using Org with recurring events or tasks: http://karl-voit.at/2017/01/15/org-clone-subtree-with-time-shift/
As Michael Maurer stated in a comment below, org-clone-subtree-with-time-shift does not ask for time-shift depending on the location of the cursor. I too had issues with not being asked for a time-shift but I was not able to determine that this is related to cursor location when org-clone-subtree-with-time-shift is invoked. Here are my test cases: *** [2017-02-28 Mi] no time-shift with cursor after [ *** <2017-02-28 Mi> no time-shift with cursor after < *** <2017-02-28 Wed> no time-shift with cursor after < *** <2017-02-28 Wed 09:00-10:00> no time-shift with cursor after < *** no time-shift with cursor after [ SCHEDULED: <2017-01-16 Mon> :PROPERTIES: :CREATED: [2017-01-16 Mon 12:32] :END: *** no time-shift with cursor after < SCHEDULED: <2017-01-16 Mon> "no time-shift with cursor after X" means that when the cursor is placed before the character X, no time-shift is being asked. If the cursor is on X or after X, the user gets asked to enter a time-shift as desired. Following test case works independent of the cursor position: *** <2017-01-16 Mon> time-shift works :PROPERTIES: :CREATED: [2017-01-16 Mon 12:29] :END: I do thing that this is a bug and not a hidden feature. Org mode version 9.0.1 (release_9.0.1-55-g51efd7) -- get mail|git|SVN|photos|postings|SMS|phonecalls|RSS|CSV|XML into Org-mode: > get Memacs from https://github.com/novoid/Memacs < Personal Information Management > http://Karl-Voit.at/tags/pim/ Emacs-related > http://Karl-Voit.at/tags/emacs/