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Currently, it's not possible to set a comment as required when flagging or unflagging an issue. We have a feature request suggesting the implementation of this ability:
Please, click on vote and watch in order to hear about updates on the development cycle.
I recognise the intention behind this but it won’t stop people from putting a blank space and clicking submit, because technically it’s a comment.
There is an education piece to be had with the people who are adding the flags and getting them to understand the importance of context along side the content.
Content is is the flag, context is the comment.
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