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Is it possible to retrieve a signed-in user's flagging history, preferably with the status of the flag?

I looked at the /me/timeline docs, and noticed it doesn't return flags. Is this type of information available via the API?

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Nope.
Neither the user_timeline object, nor the user object return any flagging information, at all. (as of API version 2.2).

The question, answer, and comment objects can return a can_flag boolean, but this does not necessarily indicate that the user has already flagged, and it returns false for a variety of reasons.

Flagging history is especially problematic as deleted items (The result of many successful flags) tend not to show in the API.

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