How to handle user who re-asks same unanswered question many times, many different ways

Question

Over the last few days, user "ArchiT3K" has been asking questions about getting his Wi-Fi Captive Portal working with iOS. No one around here seems to know how to help him, so his questions never seem to get any traction. And yet he keeps posting new questions about the same basic issue, asked a little differently each time. It's possible that he's making slight progress on figuring out his own issue, but at some point it just seems like he's just cluttering up the site by asking many, many related questions about the same topic that no one around here seems to be able to help him with.

At the time of this writing, there are 5-6 questions from him about this topic that are still on the system, and I'm sure if a mod or admin could look at what questions of his have been closed, put on-hold, or deleted over the last few days, they'll find a handful more.

What's the appropriate way to respond to this behavior? Just let it stand? Politely ask him to give it a rest? Or does this behavior cross the line into something where the admins should step in to put an end to this?

Answer 1

In my opinion, at least a few of his questions could be closed as off-topic if they aren't specifically asking something along the lines of "How can I change the configuration of my Captive Portal so that it can connect to iOS?".

If his question is about doing stuff on iOS to make iOS devices work with a given WiFi captive portal, that sounds like it would better be asked on Ask Different or some other SE site. We've tended not to encourage iOS questions in the past (as discussed here in 2011-2012), but it sounds like it may not be technically off-topic enough to put the question on hold.

This is really a gray area in my opinion. We have:

• Lots of questions: some of which can probably be closed as duplicates of one another, but not all of them (for instance, some ask about documentation, etc.). Others can be closed because the site does not allow soliciting learning material, etc. But I'm sure there are at least 3 or 4 questions that are neither off-topic nor dupes.
• A user who seems to behave in a fairly snarky way to the community (see here).
• Clear evidence that no one in the active Super User community really seems to be able to provide the answer this guy is looking for. That's not to say there isn't an answer or that his question is bad (both of these things may or may not be true), but we don't seem to have the answer here.

I think the first step is to start whittling down the questions to a smaller, more manageable number:

1. Put "On Hold" any questions that can justifiably be put on hold, as dupes or off-topic.
2. Look into closing some more questions for other reasons, though those would be harder to justify (IMO).
3. For the remaining questions, either leave them be, or drop a downvote if they just seem not to be a very good question.

I should mention that a sufficient combination of question closes and downvotes might question-ban this user, which would essentially solve "the problem" (the continued proliferation of questions) all by itself.