Almost everyone has experienced this from one side or the other. Someone flags a post with a custom reason. A moderator looks at it and realizes that the flag didn't need a custom reason. The moderator declines the flag with "flags should only be used to make moderators aware of content that requires their intervention."

The problem here is that the users don't understand why their flags are rejected in this scenario. The current messaging can be dispiriting. Examples:

At the same time, it makes sense that moderators would want to get users to stop using flags when they aren't absolutely needed. So give them a tool to do that. The current tool acts more to discourage flagging at all than to encourage correct flagging. Remember the rule of ten. If one user posts on meta to ask, there are likely nine other users that felt the same way but didn't post. Maybe some will read the meta post and adjust, but many will just decide that flagging is too confusing and do something else.

Potential Solution: add a new rejection reason. Something like "This post did not need a custom flag." It could then allow the moderator to select the correct flag that could have been used.

The user would then get a message that says something like "This post could have been flagged reason instead of getting a custom flag" where reason would be replaced with something like "Too Broad" or "Not an Answer". This would educate the user and hopefully lead to fewer custom flags in the future while keeping the user enthusiastic about normal flagging.

I'm somewhat neutral on the question of whether this should be at the level of "helpful" and "declined" or just one decline reason. I also don't care if this counts as a declined flag, although I kind of think that it shouldn't. The most important part is to get the feedback right. I do think that this should appear on the custom reason form if the last custom flag received this. That way people are more likely to see it than if it is merely under the list of flags.

Note that doing this should not clear the flags on a post. In fact, it should probably add a new one for the appropriate reason. On a post that is just short of a deletion for spam, this could push it over into deletion.

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    It's not just new users - some of the highest-rep users on my site also use custom flags when a canned reason would apply perfectly well. – David Z Dec 12 '14 at 8:37
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    I often pondered over whether a separate limit on the custom flags would be useful, such as 2 a day. But no idea if the issue is abuse >2 per day by few users, or just once by many users. – James Dec 12 '14 at 13:30
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    Custom flags mean the user has got something important to say to the mod. Putting a cap on that is counterproductive and not really democratic. Would be better to find abusers and mod ping them. – Deer Hunter Dec 12 '14 at 15:01

Frankly, a declined flag is that gentle prod. We've always had to provide a reason for declining a flag, because the primary purpose of declining a flag is to educate the flagger.

For a long time, this didn't work well at all, because people were not notified about their declined flags and few people knew to look in their flag history to see them. This led to piles of unnecessary flags coming in, and was demoralizing to moderators who saw people keep flagging poorly without learning anything about it.

The first attempt to address these poor flags was to silently ban anyone who had a bad enough history of flagging (you had to be pretty terrible at it to ever hit this), but again that did nothing to educate people.

Back in February, SE introduced the flag warning system as a better attempt to get flaggers to pay attention to why their flags might be declined. It worked, because overnight we saw people responding to these declined flags and finally reading the reasons we were providing. That's why you've seen an increase in questions about these declined flags on various Meta sites.

As a counterpoint to your assertion that

If one user posts on meta to ask, there are likely nine other users that felt the same way but didn't post."

I'd argue that the cases we see on Meta are in fact rare cases. I've personally observed many, many flaggers receive a few declined flags, read those, and immediately improve their flagging patterns. For those people, I believe the declined flags served their purpose well in changing behavior.

Take the second example you link above. The moderator who declined those took the time to write a custom response of

Please use standard close votes or close flags for this instead of flagging for moderator attention.

which I believe to be polite and to the point about what that user should do in the future. I think that very clearly answered the user's question of "I suppose that I did something wrong, but I don't know what.", but if they didn't understand the above statement a special flag response type wouldn't help them understand this any better than what was provided to them.

To be honest, most of the Meta complaints aren't about lack of understanding in a flag response, they're due to disagreements with the moderator decisions. No type of flag response is going to change that, and Meta is the only place where long-form discussions about this can occur.

All that said, I think there are things that could be done to educate certain types of flaggers before they even start flagging. For example, there is a misconception among a certain class of users that flags are to be used to demand moderators answer your question. We get these every day on Stack Overflow:

this is urgent for project due tomorrow plz answer now

and I've been working on a heuristic to identify them for quicker handling. If such a heuristic worked well, we might be able to apply it at the point of flagging to let people know what flags really should be for (like the SQL tag warning SE is tinkering with). I could see extending that for people trying to use "other" flags for standard close reasons, as well. I think that might catch a few people before they cast these flags.

  • You realize my suggestion is basically making, "Please use standard close votes or close flags for this instead of flagging for moderator attention" a standard response rather than a custom one? Yes, a good moderator can write that out. More common though is to either let it go and hope that they eventually figure it out or to flag with "flags should only be used to make moderators aware of content that requires their intervention." Neither of those solutions provide guidance. And note that in that case, the bad responses hid the good one. – Brythan Dec 12 '14 at 17:49

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