It appears this is a known issue in Confluence Server:
Could you let me know what version of Confluence you're on, so I can update the bug with your information?
A workaround would be to manually edit the HTML and include the desired checkbox: <input type = "checkbox">
Let me know if you have any questions.
We are using 6.5.0.
This issue has been opened since 2014, so I doubt there will be any fix for this issue.
And the workaround is not easy to do or practical, as most of my documents have checkboxes.
I regret that I am forced to use this application, because it lacks quite a number of commonly needed functions, or it requires a user to buy a number of plugins.
Amazing. Checkboxes are a common everyday item on documents. And this has been a design flaw open for over 3 years, no solution, and it is not even under consideration.
I cannot imagine that Confluence users have not found a solution, not even a simple 'checkbox' add-on. I guess this community is not big enough for someone to provide simple solutions.
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