As we know questions with bounties on them can't be closed unless they are flagged for mod attention. The rationale seems to be that

  1. bounties can only be offered for questions at least two days old (and thus, presumably, close-worthy posts never get to have a bounty offered for them),
  2. existing close votes can be wrong so these shouldn't prevent bounties to be offered, and
  3. automatically refunding the bounty amount to the funder in case of allowed close-votes would open the way to foul play.

The problem is that in tags with less traffic it can easily happen that questions that should be closed go under the radar for 2 days. When a bounty is posted, these off-topic or unanswerable questions shine like beacons, drawing in all sorts of low-quality and high-quality answers.1 When custom moderator flags are raised on these questions, these take time to be handled. I've had flags raised on fairly fresh (1 day old) bounty offers, only to be handled well after the bounty was over.2 My impression is that mods are constantly somewhat overwhelmed, and they of course select their workload among the pool of waiting flags. I imagine that bounty flags are on the high-effort side of the cognitive power scale needed to handle flags, so these tend to stick around in the moderator queue.

My suggestion is to partly prioritize flags on bounty questions by distinguishing them from the pool of generic moderator flags. I could imagine that attempted close votes on bounty questions could raise this flag (in order not to have a special kind of flag introduced into the flag dialog). The 7-day time limit of bounties implies that any action taken on these posts should be done sooner than later. Due to the additional visibility of bountied off-topic (too broad, unclear, etc.) posts, they proportionally cause more harm to the site if left open. And while these flags might still be neglected due to the moderators being overwhelmed, at least they wouldn't be lost in a proverbial haystack of generic flags.

1I don't want to start a discussion about whether otherwise good answers on blatantly ill-fit questions benefit or harm the site in the long run.
2One specific example I found in my flag history: flagged bounty 25 hours after its start, flag marked as helpful 20 hours after the bounty had ended (4 days after my flag), with the reason "With the bounty now gone, you are free to vote to close."

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    Mods are extremely reluctant to close bountied questions. Prioritizing won't encourage them to change that stance at all. I personally couldn't get them to close a bountied April 1st joke, got a "learn how to use flags" reject. Pah, resistance is futile. Something to bring up for the next mod election. – Hans Passant Nov 25 '17 at 17:52
  • It could use some meta effect btw, feel free. – Hans Passant Nov 25 '17 at 17:53
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    @Hans I've yet to see explicit feedback that suggests anything along the lines of "leave these posts alone"/"we don't care about these posts". The linked questions I found on meta all suggest that these posts should be closed and should be flagged, so I'm trying to be optimistic and think that the reason is partly due to technical limitations ;) – Andras Deak Nov 25 '17 at 18:08
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    @Andras I'll write up my thoughts of this later tonight or tomorrow - we've kicked it about the mod room occasionally but it's just not a big thing in the grand scheme of things... Never hurts it have a proper response though on how to do things and what things will be followed. (It won't be a mod-team/site response though, just my thoughts so maybe we can thrash it out once and for all) – Jon Clements Nov 25 '17 at 18:29
  • Awesome, @Jon, thanks and looking forward to it :) It's also fine if you post it on one of the linked [discussion] posts in case that makes more sense. – Andras Deak Nov 25 '17 at 18:35
  • @HansPassant As the person who offered up that particular bounty, I'm sorry. It did seem like a funny idea at the time. (Also, I expected it to be immediately closed, and wasn't aware/forgot that bounties acted as magic close vote shield) – Brant Bobby Nov 28 '17 at 15:51

We don't really need more generic moderator flags. We have plenty, thank you! (Just kidding, everyone...)

Seriously, though: just flag the post with a custom flag, like,

This should be closed because [reason goes here], but there's a bounty.

This is one of those rare instances where a somewhat-detailed custom flag is helpful. If you just say, "Too broad," we're likely to decline it because it doesn't require moderator attention. We aren't likely to go look at the question to see if there's an open bounty, and we can't see that in the normal moderator tools.

If we need to, we can remove/refund the bounty. If it has already been awarded, we can escalate it for the SO staff to do it. Generally, though, bounty points are lost once offered. It's on the user offering the bounty to make sure the post is a reasonable one, not one that would otherwise get closed.

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    My feeling is that this advice mostly refers to declined flags. My problem is flags not getting handled at all (until it's too late). All my custom mod flags are detailed (probably to a fault). The problem is that a lot of off-topic questions eventually get answers with a lot of effort put into them, at which point nobody will say "OK, this question should've been closed, so let's undo the bounty". So we'll end up with a bulletin demonstrating that such questions (and having them answered) are welcome on the site. – Andras Deak Nov 25 '17 at 20:03
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    To be clear, I understood your issue was with speed. I'm saying the best way to handle it is still a custom flag. Automatic flags here would be worse. Flag-handling speed is always an issue. We get lots of flags, and some of them (especially the custom ones) are really tough calls. But we will still handle them all eventually. If somebody puts a lot of effort into writing a really detailed answer to a question that's obviously going to be closed, that's their problem, not ours. We'll still put the question on hold if we need to, and in really bad instances we will still revert the bounty. – elixenide Nov 25 '17 at 20:07
  • Thanks, I'll keep that in mind and take you at your word when needed ;) – Andras Deak Nov 25 '17 at 20:09
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    "We aren't likely to go look at the question to see if there's an open bounty, and we can't see that in the normal moderator tools." Exactly. The real problem is that moderator flag tools need... retooling. Just like every review queue should expose the up/down vote options, the moderator flag queue should show more context. IMO it should show full context for any custom flags. – TylerH Nov 27 '17 at 14:44
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    @tylerh No question, more context would be helpful when there is such context. The mod tools need improvement, but the biggest and hardest-to-solve issue is still that we have ~20 people at any given time trying to handle 2,000+ flags in a day. Ultimately, that’s always going to require prioritizing speed in most situations. – elixenide Nov 27 '17 at 15:19
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    Why do you assert that "somewhat-detailed custom flag[s]" are typically unhelpful? – jpmc26 Nov 28 '17 at 15:52
  • @jpmc26 Most of them either (1) should have been one of the standard flags or (2) are full of unnecessary information. We handle flags by type, so, for example, we can handle lots of "not an answer" (NAA) flags at once. A custom flag that says, "This is not an answer because Python 2.7 blah blah blah" doesn't go into that list and thus takes more time to handle. Too many custom flags boil down to, "There's no rule that X is inappropriate, and none of the standard flags fit it, so here's a manifesto on why X is bad." In short, useful detail = good, whiny detail = bad. – elixenide Nov 28 '17 at 17:57
  • @EdCottrell I disagree those are whiny, even if they're not how flags are supposed to be used. Anyway, it sounds like what you're describing goes back to the age old debates around how "Not an Answer" is supposed to be used and what should be flagged and what shouldn't. – jpmc26 Nov 28 '17 at 19:09
  • @jpmc26 I hope you understand that I can't quote actual custom flags here. Trust me when I say many of them are whiny, such as the "this downvote was unfair" or "my question shouldn't be put on hold just because it's off-topic" varieties. And no, my point isn't about what is and isn't appropriate for the NAA flag. All I said was, "This is one of those rare instances where a somewhat-detailed custom flag is helpful." Most, not all, custom flags we receive either should be (1) a standard flag or (2) less detailed. This is all just a side point to my answer to the actual question. – elixenide Nov 28 '17 at 19:41
  • @EdCottrell I am only trying to understand. I agree the latter examples you gave are whiny. Your first response, though, focused strongly on flags that remind me of the NAA debates, where the context of the question might help sometimes. Hopefully having a better understanding now, I don't think your answer really gets that particular point across. The usual problem doesn't really seem to be the level of detail; it seems to be the misuse of custom flags in general. Many are simply invalid flags, and the rest don't need to clarify extenuating circumstances. The NAA type may be a gray area. – jpmc26 Nov 28 '17 at 23:11
  • @jpmc26 To be clear, my answer isn’t about flagging generally or even about custom flags. My answer is, “Raise a custom flag.” The rest of the answer just unpacks that. It’s not intended to discuss the full scope of appropriate and inappropriate flags. These comments are now pretty far off-topic. If you would like to ask a question about flagging, please ask a new question instead of commenting on an answer that is only about one very specific use case for custom flags. – elixenide Nov 29 '17 at 0:18
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    @EdCottrell My comments are not off-topic; they are seeking clarification and improvement of the post to which they are attached, the primary purpose for comments. You chose to mention this broader issue in passing in your answer. That's fine; there's no rule against bringing up related issues. However, if a user does so, I expect them to be clear about what they are saying. This is especially true when a moderator answers on Meta, since their words carry significantly more weight. I hope you will either edit to clarify or remove the mention if you do not wish to bother. – jpmc26 Nov 29 '17 at 10:42
  • @jpmc26 I think my statement was clear. And these comments have gotten pretty far afield from the post. There’s really no value to continuing this discussion in this context. Again, if you want to ask a new question about flags, feel free to do so, or read one of the many questions people have already posted on these topics. – elixenide Nov 29 '17 at 11:25
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    So...anecdotal evidence: my last bounty close flag I raised on Nov 23 (two days before posting this question, right when the bounty was fresh on the question) finally got handled. On Dec 18. That's 25 days or so. I know you said "But we will still handle them all eventually", but this is completely useless for bounty flags. – Andras Deak Dec 22 '17 at 22:34
  • @AndrasDeak again, when necessary we can elevate things to the developers’ attention to get the bounty reversed. The important thing is that my advice above is still the correct way to handle the situation. We had a big flag backlog due to the schedules of the various moderators. While we have the backlog back under control now, raising an incorrect or unclear flag would only have slowed it down further (or resulted in us declining it because critical information was missing). Moderator bandwidth is always a challenge, but that doesn’t change what you should do when you see issues on the site. – elixenide Dec 22 '17 at 22:43

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