After careful consideration, I believe it is most prudent to only introduce a defcustom variable. This will allow for modification while simultaneously preserving the current behavior. Currently we can change the value of "org-columns-checkbox" with the following keybindings: (1) C-c C-c (org-columns-toggle-or-columns-quit) Same behavior to toggle checkbox as 'C-c C-c (org-toggle-checkbox)' on "org-checkbox". It's a great idea that keybinding works in the same way as in the case of a regular checkbox. This provides a consistent interface for the "org-checkbox" and "org-columns-checkbox". So every user who starts using "org-columns" will try to use the same keybinding they used for "org-checkbox". That's how I used it too. But I would not implement other keybindings from "org-checkbox": C-u C-c C-c (org-toggle-checkbox) - add or remove checkboxes. C-u C-u C-c C-c (org-toggle-checkbox) - set the checkbox to "[-]". Because there are too complicated and uncomfortable. And this functionality can be easily replaced by adding defcustom variable and using keybinding describe in point (3) of this mail. (2) n or S-RIGHT (org-columns-next-allowed-value) p or S-LEFT (org-columns-previous-allowed-value) Later on, I started using S-RIGHT & S-LEFT. It's simply more convenient than 'C-c C-c' because in "org-columns" we navigate with arrow keys. So, the right hand is always on the arrow keys, making it easier now to press just one SHIFT key with the left hand to change the value. When we have the default two states "[X]" and "[ ]", behavior is same as 'C-c C-c' - toggle within these two states. But if we add the third state "[-]", it might not be well-received by users who use these keybindings, because now they would have to additionally cycle between those three states, not just two. And unfortunately, they wouldn't be able to change it. That's why I believe it's worth introducing a defcustom variable. (3) 1..9,0 "Directly select the Nth allowed value, 0 selects the 10th value." Now that's how I change the values in the "org-columns-checkbox". Because it's by far the fastest, simplest, and most convenient way. Only one key and I immediately have the state I want. Right now I'm using 4 states for "org-columns-checkbox": (setq org-columns-checkbox-states '("[X]" "[-]" "[ ]" "" )) So empty state "" at digit '4' I have option to remove checkbox. Digit '2' is "[-]". Super easy and convenient in comparison to: C-u C-c C-c (org-toggle-checkbox) - add or remove checkboxes. C-u C-u C-c C-c (org-toggle-checkbox) - set the checkbox to "[-]". What do you think? Patch in attachment.