I discovered that when trying to insert a new item with a checkbox using
M-S Return (org-insert-todo-heading), the keybinding is "translated" to
M-Return (org-meta-return). As a result, all I get is simple list item
without a checkbox.

M-x describe-key [Ret] M-S Ret

...shows the following...

--8<---------------cut here---------------start------------->8---
M-RET (translated from <M-S-return>) runs the command org-meta-return
(found in org-mode-map), which is an interactive compiled Lisp
function in ‘org.el’.

It is bound to M-RET, C-c C-x RET.
 
(org-meta-return &optional ARG)
--8<---------------cut here---------------end--------------->8---

A git bisect traced the source of this problem to the following commit:

--8<---------------cut here---------------start------------->8---
6965098a5357b09575a1119074545eb708cf5944 is the first bad commit
commit 6965098a5357b09575a1119074545eb708cf5944
Author: Nicolas Goaziou <m...@nicolasgoaziou.fr>
Date:   Mon Jan 15 16:13:37 2018 +0100

    Use a single keybinding representation

    * lisp/org.el (org-replace-disputed-keys): Fix docstring.

    Use `kbd' macro everywhere.  Also add missing "ESC" equivalents for
    "M-" bindings.
--8<---------------cut here---------------end--------------->8---

Thanks,
Matt

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