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I'm planning on going through the archives of a chat room, and flagging a large number of past chat messages. (The flagging will be of messages from multiple users, not just one particular user, and the chat messages from "You Are Here", not from other chat rooms)

Should I flag them all at once, or just do a small number at a time?

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    ... why? This sounds like a profound waste of your time and everyone else's. – Adam Lear Jun 9 '14 at 1:26
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    If you're annoyed that you're banned from chat, this isn't going to help in any sense whatsoever. If anything, it'll just make it worse. – fbueckert Jun 9 '14 at 1:53
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    Have you considered that doing so will probably make you a worse offender, than any of those chat users, for wasting time of everyone who is notified of those chat flags? – user1306322 Jun 9 '14 at 8:03
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    @AnnaLear there's been a lot of discriminatory content in that chat room. I've flagged some of it in the past, but not all of it. – Andrew Grimm Jun 9 '14 at 8:44
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Don't.

If a post is really really really really bad, then you can annoy the mods. If you can find a huge number of them that have slipped past people in the room, you don't understand what a flag is.

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As has been noted already, I agree this would be a very bad idea. It would create a lot of flag noise. I don't have much to add on that front...

If you really think there is a long-term pattern from some individuals that is far beyond the pale of being questionable, a better method would be a single flag to moderators, or perhaps even a staff contact. From there, you could link to some representative samples and express why you think the pattern of posts is bad.

But do keep in mind that chat is a quite different thing than the main sites themselves. Standards are much more loose for behavior, and they are relative to the regular users in the individual chatrooms. That is; if the regular users of a chatroom find some particular behavior to be acceptable, it's more likely to be OK.

That doesn't mean "anything goes". There are still some over-arching rules that apply. I know nothing at all of any specifics you might be referring to, but if you are truly convinced there is a big problem, I'd suggest my advice above - and then please leave it up to those you contact to deal with it appropriately.

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You shouldn't flag any of them. Flags are broken by design and will only draw attention to the content while not causing anything to be done about it. Essentially what you will do is spam the 10k users who are currently in chat with content from a long time ago.

If the content is from a significant amount of time ago, then it is set in stone in a sense. As the room clearly moved on since then, the content is not negatively detracting from the chat room.

I believe that people have a very unfortunate misunderstanding when it comes to flags in the chat rooms. This probably stems from the flagging system in the exchange. Chat room flags do not have the same feature coverage that the main sites do. Moderators will not eventually review a flag, only the 10k users will.

Do not spam flags in chat, it only annoys people. If there is a concern about a particular user, flag any one of their posts "for moderator" one time and explain the issue. That is essentially the only option for moderation chat has.

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