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I am using factory default Emacs and Org-mode settings.
I am using the following org todo item:
#+BEGIN_SRC org
* TODO EXAMPLE
SCHEDULED: <2020-08-09 Sun>
DEADLINE: <2020-08-09 Sun>
#+END_SRC
It is expected that on the date 2020-08-09 I will see 2 lines in my Org
agenda: one with "Scheduled:" leader text, while the other with
"Deadline:" leader text.
What happens instead is that one of the lines show "Scheduled:" leader
text, and the other line shows no leader text at all.
Also, consider changing the order of the SCHEDULED and DEADLINE properties:
#+BEGIN_SRC org
* TODO EXAMPLE
DEADLINE: <2020-08-09 Sun>
SCHEDULED: <2020-08-09 Sun>
#+END_SRC
In this case it will be only the "Deadline:" leader text shown on one of
the lines, while the other line shows no leader text at all.
Therefore my assumption, is that somehow only the first of the
properties is taken into account, while the property which comes second
is ignored.
As stated earlier, the expected behaviour is that both leader/warning
texts are displayed on their appropriate line entry.
Emacs : GNU Emacs 26.1 (build 2, x86_64-pc-linux-gnu, GTK+ Version 3.24.5)
of 2019-09-23, modified by Debian
Package: Org mode version 9.1.9 (release_9.1.9-65-g5e4542 @ /usr/share/emacs/26.1/lisp/org/)