I have tried a dozen different ideas to add a checkbox to a richtext field.
The text is rendered as a static "[" "]". I have tried many combinations of syntax.
I can edit the work item and use the Wysiwyg editor by typing [] or using the tool bar.
BUT
I have a use case that can use automation to speed up a very manual task,
based on values in other fields, I want to add check boxes to a specific field.
That feature is not supported with the built-in markdown rules can use...the same as many of the rich text macros.
I recall there is an open suggestion to add the feature, and a workaround may be possible using the REST API with the Atlassian Document Format (ADF) syntax to add a task list item.
Kind regards,
Bill
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