>From "emacs -Q":

Save the attached file, make it ready-only, visit the file, move point
to the start of the line with the first checkbox, type C-C C-c.  I get a
message "Cannot update this checkbox".  That's fine, the file and buffer
are read-only.

-*-org-*-

- [ ] box1
- [ ] box2
- [ ] box3
- [ ] box4
- [ ] box5
Make the file read-write (e.g., in dired, or with a shell chmod
command).  Revert the buffer, notice that the read-only indication is
gone from the modeline.

Again type C-c C-c.  I still get "Cannot update this checkbox".  I
expect the checkbox to be updated.

Kill the buffer and visit the file again.  Notice that the modeline
indicates read-write access.  Type C-c C-c.  I *still* get "Cannot
update this checkbox".  I expect the checkbox to be updated.

FWIW, if point is in a different part of the line, e.g., inside the
checkbox, the message is "Cannot toggle this checkbox: unchecked
subitems".

I first saw this with a build based on Emacs git hash 7a7258984710.  But
I can also reproduce the problem with Emacs 30.1 (Org Mode 9.7.11).

regards,
mike

Emacs  : GNU Emacs 31.0.50 (build 3, x86_64-pc-linux-gnu, X toolkit, cairo 
version 1.16.0, Xaw scroll bars)
 of 2025-03-21
Package: Org mode version 9.7.11 (release_9.7.11 @ 
/usr/new/share/emacs/31.0.50/lisp/org/)

current state:
==============
(setq
 org-yank-image-file-name-function 'org-yank-image-autogen-filename
 org-persist-before-write-hook '(org-element--cache-persist-before-write)
 org-speed-command-hook '(org-speed-command-activate
                          org-babel-speed-command-activate)
 org-persist-after-read-hook '(org-element--cache-persist-after-read)
 org-confirm-elisp-link-function 'yes-or-no-p
 org-mode-hook '(#[0 "\300\301\302\303\304$\207"
                   [add-hook change-major-mode-hook org-fold-show-all append
                    local]
                   5]
                 #[0 "\300\301\302\303\304$\207"
                   [add-hook change-major-mode-hook org-babel-show-result-all
                    append local]
                   5]
                 org-babel-result-hide-spec org-babel-hide-all-hashes)
 org-confirm-shell-link-function 'yes-or-no-p
 org-archive-hook '(org-attach-archive-delete-maybe)
 org-metaup-hook '(org-babel-load-in-session-maybe)
 org-occur-hook '(org-first-headline-recenter)
 org-bibtex-headline-format-function 'org-bibtex-headline-format-default
 org-link-parameters '(("attachment" :follow org-attach-follow :complete
                        org-attach-complete-link)
                       ("id" :follow org-id-open :store
                        org-id-store-link-maybe)
                       ("eww" :follow org-eww-open :store org-eww-store-link)
                       ("rmail" :follow org-rmail-open :store
                        org-rmail-store-link)
                       ("mhe" :follow org-mhe-open :store org-mhe-store-link)
                       ("irc" :follow org-irc-visit :store org-irc-store-link
                        :export org-irc-export)
                       ("info" :follow org-info-open :export org-info-export
                        :store org-info-store-link :insert-description
                        org-info-description-as-command)
                       ("gnus" :follow org-gnus-open :store
                        org-gnus-store-link)
                       ("docview" :follow org-docview-open :export
                        org-docview-export :store org-docview-store-link)
                       ("bibtex" :follow org-bibtex-open :store
                        org-bibtex-store-link)
                       ("bbdb" :follow org-bbdb-open :export org-bbdb-export
                        :complete org-bbdb-complete-link :store
                        org-bbdb-store-link)
                       ("w3m" :store org-w3m-store-link)
                       ("doi" :follow org-link-doi-open :export
                        org-link-doi-export)
                       ("file+sys") ("file+emacs")
                       ("shell" :follow org-link--open-shell)
                       ("news" :follow
                        #[514 "\301\300\302Q\"\207"
                          ["news" browse-url ":"] 6
                          ("/usr/new/share/emacs/31.0.50/lisp/org/ol.elc" .
                           51119)
                          ]
                        )
                       ("mailto" :follow
                        #[514 "\301\300\302Q\"\207"
                          ["mailto" browse-url ":"] 6
                          ("/usr/new/share/emacs/31.0.50/lisp/org/ol.elc" .
                           51119)
                          ]
                        )
                       ("https" :follow
                        #[514 "\301\300\302Q\"\207"
                          ["https" browse-url ":"] 6
                          ("/usr/new/share/emacs/31.0.50/lisp/org/ol.elc" .
                           51119)
                          ]
                        )
                       ("http" :follow
                        #[514 "\301\300\302Q\"\207"
                          ["http" browse-url ":"] 6
                          ("/usr/new/share/emacs/31.0.50/lisp/org/ol.elc" .
                           51119)
                          ]
                        )
                       ("ftp" :follow
                        #[514 "\301\300\302Q\"\207" ["ftp" browse-url ":"]
                          6
                          ("/usr/new/share/emacs/31.0.50/lisp/org/ol.elc" .
                           51119)
                          ]
                        )
                       ("help" :follow org-link--open-help :store
                        org-link--store-help)
                       ("file" :complete org-link-complete-file)
                       ("elisp" :follow org-link--open-elisp))
 org-persist-directory "/tmp/org-persist-vs44GD"
 org-cycle-tab-first-hook '(org-babel-hide-result-toggle-maybe
                            org-babel-header-arg-expand)
 org-agenda-before-write-hook '(org-agenda-add-entry-text)
 org-metadown-hook '(org-babel-pop-to-session-maybe)
 org-tab-first-hook '(org-babel-hide-result-toggle-maybe
                      org-babel-header-arg-expand)
 org-sort-function 'string-collate-lessp
 org--warnings nil
 org-babel-pre-tangle-hook '(save-buffer)
 org-export-before-parsing-hook '(org-attach-expand-links)
 org-link-shell-confirm-function 'yes-or-no-p
 org-fold-core-isearch-open-function 'org-fold--isearch-reveal
 outline-isearch-open-invisible-function 'outline-isearch-open-invisible
 org-src-mode-hook '(org-src-babel-configure-edit-buffer
                     org-src-mode-configure-edit-buffer)
 org-agenda-loop-over-headlines-in-active-region nil
 org-link-elisp-confirm-function 'yes-or-no-p
 org-cycle-hook '(org-cycle-hide-archived-subtrees org-cycle-show-empty-lines
                  org-cycle-optimize-window-after-visibility-change
                  org-cycle-display-inline-images)
 org-persist-before-read-hook '(org-element--cache-persist-before-read)
 )

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