indent-region indents the region according to the current mode.
In a Lisp mode (e.g. emacs-lisp-mode), selecting that as the region and using TAB indents it as you say you expect, not as you show.
Why would expect it to behave similarly in Org mode?
(The section of the tutorial that you cite doesn't say anything about indentation, BTW.)
C-h f indent-...
I am currently discussing a potential patch for as an answer to this question.
The code that answers my original question looks like this:
(= (point) calculate-lisp-indent-last-sexp)
(eq (char-after (1+ containing-sexp)) ?:)
(eq (char-before containing-sexp) ?')
(let ((quoted-p nil)