Is it possible to add a watcher to an issue if custom field checkbox is checked when moving from one status to another? If the checkbox is not checked then do not add the person to the watcher list? This is for a cloud instance.
Unfortunately out of the box this is not possible. You could achieve this with Automation for Jira (AFJ). AFJ is a powerful add on that expands on the default automation of JSD and allows it to be used in regular Jira projects.
They have a free version that has no features lost except you do have a 300 automation run cap per month.
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