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When I flag some question, answer or comment, I would expect the flag button to turn into some "undo" button or just disappear, but it seems to stay the same. And when a flag is declined, the button is still there even when somebody decided that flagging the post was not justified.

How does the flag system work with regard to flagging multiple times or taking back flags?

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When I flag some question, answer or comment, I would expect the flag button to turn into some "undo" button

Well, it sort of does; if the flag hasn't been processed yet, you'll be able to 'Retract' the flag. (This only works for post flags.)
For comments you have flagged, the flag link isn't clickable anymore in that case, just like you indicate to expect.

But, when a flag has been processed (declined, marked helpful, disputed) or retracted or aged away you can cast another flag on the same post or comment; just not one of the same 'severity' (except for when it has aged away).

Example: after your spam flag has been declined, you can still cast a Very Low Quality or Not An Answer flag. If you retract that flag yourself, you can still cast a custom moderator flag. Generally speaking, you can have at most one active flag on a single post or comment at a time.

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  • Does this mean, when for example some guideline changed that a declined flag could be issued again without somebody declining it as "you already flagged the post and the flag was declined"? I am a bit curious, as ther sites seem to set a permanent "you flagged it" bit disregarding how the flag was processed. – allo Jul 10 '18 at 12:20
  • Yes, that part "You have retracted this type of flag" / "This is the flag you currently have raised" / "You have already raised this type of flag" is permanently shown. I don't think we'll see a change in this behaviour; "when for example some guideline changed that a declined flag could be issued again without somebody declining it" that's not likely to happen. – Glorfindel Jul 10 '18 at 12:27

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