Tweak checkbox support in Org DWIM command

config.org

@@ -3484,7 +3484,7 @@ Annoyingly, the only good way to fix these issues is to completely override the
 
 #+begin_src emacs-lisp
 (defadvice! ~/org-dwim (old-fn &optional arg)
-  "Only toggle overlays in headlines if there is nothing else to do."
+  "Various tweaks to the function of the DWIM command."
   :override #'+org/dwim-at-point
   (if (button-at (point))
       (call-interactively #'push-button)
@@ -3580,7 +3580,11 @@ Annoyingly, the only good way to fix these issues is to completely override the
                 (org-element-property :end lineage))
              (org-open-at-point arg))))
         ((guard (org-element-property :checkbox (org-element-lineage context '(item) t)))
-         (org-toggle-checkbox))
+         (org-toggle-checkbox)
+         (unless arg
+           (org-next-item)
+           (beginning-of-line)
+           (re-search-forward "\\[.\\] ")))
         (`paragraph
          (+org--toggle-inline-images-in-subtree))
         (_