org-agenda not showing missed deadlines

Question

today I have to ask the community for some help. I used my org-agenda for a few years now. But since a few month my missed deadlines wont be shown in weekly agenda. Maybe I miss-configured something during continues cleanup but I dont find a bad configuration.

I already tried a clean only org-mode installed config but it also does not work, no warnings of missed deadlines :-(

Documentation for deadlines writes "In addition, the agenda for today will carry a warning about the approaching or missed deadline, starting org-deadline-warning-days before the due date, and continuing until the entry is marked DONE." So actually no magic.

My Emacs-Version: GNU Emacs 26.3

My Org-Version: 9.3.1

My org-mode config:

(use-package
  org

  :mode
  ("\\.org\\'" . org-mode)

  :commands
  (org-agenda
   org-capture-todo
   org-capture-todo-context
   org-capture-journal
   org-capture-calendar)

  :config
  (setq
   org-gtd-directory "~/.gtd/"
   ;; org-gtd-todos-file (expand-file-name "todos.org" org-gtd-directory)
   ;; org-gtd-journal-file (expand-file-name "journal.org" org-gtd-directory)
   org-gtd-todos-file (expand-file-name "gtd.org" org-gtd-directory)
   org-gtd-journal-file (expand-file-name "gtd.org" org-gtd-directory))

  (setq
   org-startup-indented t
   org-M-RET-may-split-line t
   org-default-notes-file org-gtd-todos-file
   org-outline-path-complete-in-steps nil
   org-refile-use-outline-path t
   org-blank-before-new-entry '((heading . nil) (plain-list-item . nil))
   org-agenda-files (list org-gtd-todos-file)
   org-todo-keywords '((sequence "TODO(t)" "STARTED(s)" "BLOCKED(b)" "|" "DONE(d)" "DELEGATED(g)" "CANCELED(c)"))
   org-tag-alist '(;; For exclusiv groups
                   ;; (:startgroup . nil)
                   ;; ("@work" . ?w) ("@home" . ?h)
                   ;; ("@tennisclub" . ?t)
                   ;; (:endgroup . nil)
                   ("GENERAL" . ?g) ("EMACS" . ?e))
   org-refile-targets '((org-agenda-files :maxlevel . 5)))

  (setq
   org-capture-templates
   '(("t" "Todo (without context)" entry (file+headline org-gtd-todos-file "Inbox")
      "* TODO %? %i %^g\n:PROPERTIES:\n:ADDED: %U\n:CONTEXT:\n:DEADLINE: %^t\n:END:")
     ("T" "Todo (with context)" entry (file+headline org-gtd-todos-file "Inbox")
      "* TODO %? %i %^g\n:PROPERTIES:\n:ADDED: %U\n:CONTEXT: %a\n:DEADLINE: %^t\n:END:")
     ("j" "Journal" entry (file+headline org-gtd-journal-file "Journal")
      "* %? %i %^g\n:PROPERTIES:\n:ADDED: %U\n:CONTEXT: %a\n:END:")
     ("c" "Calendar" entry (file+headline org-gtd-todos-file "Calendar")
      "* TODO %? %i %^g\n:PROPERTIES:\n:ADDED: %U\n:CONTEXT: %a\n:SCHEDULED: %^T\n:DEADLINE: %^t\n:END:")))

  (defun org-capture-todo ()
    (interactive)
    (org-capture nil "t"))

  (defun org-capture-todo-context ()
    (interactive)
    (org-capture nil "T"))

  (defun org-capture-journal ()
    (interactive)
    (org-capture nil "j"))

  (defun org-capture-calendar ()
    (interactive)
    (org-capture nil "c"))

  :bind*
  (("C-M-- <RET>" . org-capture)
   ("C-M-- t" . org-capture-todo)
   ("C-M-- T" . org-capture-todo-context)
   ("C-M-- j" . org-capture-journal)
   ("C-M-- c" . org-capture-calendar)
   ("C-M-- a" . org-agenda)))

My example org-file:

* TODO TEST A                                                       :GENERAL:
:PROPERTIES:
:ADDED: [2020-01-05 Sun 16:47]
:DEADLINE: <2020-01-08 Wed>
:END:
* TODO TEST B                                                       :GENERAL:
:PROPERTIES:
:ADDED: [2020-01-05 Sun 16:47]
:DEADLINE: <2020-01-16 Thu>
:END:

My agenda output:

Week-agenda (W03):
Monday     13 January 2020 W03
Tuesday    14 January 2020
Wednesday  15 January 2020
Thursday   16 January 2020
  gtd:        TODO TEST B                                                               :GENERAL:
Friday     17 January 2020
Saturday   18 January 2020
Sunday     19 January 2020

Expectation: TEST A schould be shown as missed deadlined task.

Any ideas what I missed, hopefully someone can help me, thx.

Answer 1

You are setting your deadline incorrectly. The normal way of setting a deadline is as follows:

* MY-TEST :GENERAL:
DEADLINE: <2020-01-13 Mon>

Your entry should thus look like this:

* TODO TEST :GENERAL:
DEADLINE: <2020-01-13 Fri>
:PROPERTIES:
:ADDED: [2020-01-14 Tue 16:47]
:END:

DEADLINE is not an ordinary org property.