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Someone's currently going through old questions (typically ones at least a year old) and flagging the ones requesting tools for closure. Is this an appropriate thing to do?

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Guilty, so here are my thoughts.

Let's keep this in mind: so far, every single flag I've raised has been labeled as "helpful" which means that these questions were indeed off-topic.

Why not just leave these questions alone?

We have a review queue about this and it's called "Late Answers". For example, so far today there were 3 late answers which means that eventually, someone will post in one of them (them being the off-topic questions) when the question itself should be closed in the first place.

Neal suggested to edit these questions and to be fair, most of them seem irrecuperable because they are blatantly requesting for X product doing Y. Also, like I said in the comments, it would also bring them up in the feed, which is what we probably want to avoid.

Is there a written rule against this?

As far as I know, nope (feel free to correct me if I'm wrong).

Also, what also makes me believe that this is not wrong is that we can a maximum of up to 100 flags per day! Therefore, I do not see why one should be refrained from flagging many questions in a somewhat short length of time.

Now about flagging old questions, if this is inappropriate, why are we able to do so then? Simply because it does not mean that it's a good and/or appropriate question because it never got flagged.

There has to be something negative this could cause, right Mr. Simon?

Sure, it fills up the queue with questions that don't need immediate care. Therefore, if you flag a bunch of questions, a newer question might not be reviewed because the reviewers maxed out their review cap (I feel like I should stop typing "review"). That, indeed, can cause trouble.

What should be the proper behavior?

Well, as suggested by the almighty @AviD in the chat, flagging a few questions at a time to avoid filling up the queue is probably the best way to act. Personally, I'm still unsure if we should edit these questions at all considering that most of them seem to be a lost cause.

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  • Thanks for posting more info. Can you add a list of the questions you flagged, or a random sample, so we don't have to talk in generalities? I don't see a way to query for them otherwise. – nealmcb Sep 8 '14 at 23:23
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    @ Whoever downvoted, how about you leave a comment with an explanation instead of not showing yourself? – Simon Sep 9 '14 at 0:55
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    I haven't reviewed all the questions you flagged, but so far they don't seem to be in need of closing. There is a close reason “: Questions seeking product recommendations are off-topic as they become obsolete quickly. Instead, describe your situation and the specific problem you're trying to solve.” But the questions you flag do describe the situation and the specific problem to solve. – Gilles 'SO- stop being evil' Sep 9 '14 at 10:24
  • Furthermore, if the questions did need closing, then they should indeed be closed. But a large-scale effort like this should be discussed on meta first. – Gilles 'SO- stop being evil' Sep 9 '14 at 10:25
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    Fair enough, thanks for your input @Gilles. – Simon Sep 9 '14 at 15:01
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    I think of the ones you flagged that I then reviewed, I did close 1 or 2. Where I saw there were answers with quite a few upvotes I figured I'd just leave them. They are old questions, they helped someone, and while they may have been posts from our early days they still appear useful. I'm okay with them being flagged though - it doesn't take long to quickly review them. – Rory Alsop Sep 11 '14 at 9:47
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The presence of a reasonably successful site like https://softwarerecs.stackexchange.com/ demonstrates that software recommendations can be handled effectively in the stackexchange format. But for a field as specialized and often counter-intuitive as security, I think keeping the questions here is typically a benefit.

It is often harmful to close, and not delete, old questions which already have helpful answers. We would typically be left with questions which over time will have bad answers, because new and improved tools will come along. Deleting them is often even more unhelpful, as a waste of admin energy, a source of needless debate, and a loss of useful information.

The appropriate action is to improve the question with edits which demonstrate best practice, by making sure it is clear just what the requirements are for the tool, so that there is a good answer. When there is a good accepted answer, such edits should typically make it so that the question matches the answer.

It is also bad form to suddenly flag lots of questions, before discussing goals and strategies with the community.

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  • Editing these questions would bring them up in the feed, which would most-likely not be the best solution. – Simon Sep 8 '14 at 22:40
  • Just to be clear, which "feed" are you talking about - Recently Active Questions? Assuming it is a good edit, seems like no big problem to see it in that feed. – nealmcb Sep 8 '14 at 23:03
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    I am a moderator of Software Recommendations SE and I fully approve this answer. SR.SE's biggest default is that questions get few answers because they aren't reaching the right audience. If you want recommendations of security tools, ask security professionals — here. We haven't had a moderation problem with recommendation requests like Stack Overflow and Super User have, so we don't need to make them off-topic. And this absolutely should have been discussed on meta beforehand. – Gilles 'SO- stop being evil' Sep 9 '14 at 10:18

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