How do you deal with users that don't break the rules, but are always walking the line?

Question

We had several users that tried very hard to walk just above the line of breaking the rules and not actually break them.

How should they be handled?

Answer 1

If they aren't breaking rules and they are just being annoying then the appropriate course of action is to watch them while publicly ignoring them. They are testing their boundaries. Let them. When they cross the line, tell them so and follow your communities procedures in dealing with it.

Ignoring them publicly (not saying "yes this is ok", "no this is not ok") also reduces their entertainment value. It sounds like they are baby trolls. Like any small child, the easiest way to get a kid to stop doing something you don't like is to completely ignore it. It works with trolls too. If you react, either positively or negatively, you've given them the attention they are seeking. Eventually, they will either find the limits of their boundaries, grow bored of testing you, or cross the line.

Answer 2

Personally I'd treat them as trolls. Most communities I've been in will have a clause in the rules that you need to follow both the letter and spirit of the rules, which stops people getting around this.

For larger sites this can be harder as spirit of the rules is subjective and whilst fine for smaller communities ends up with endless discussions in larger ones with lots of moderators interpreting the spirit of the rules. For larger communities a large list of rules on trolling should be present and then users who persistently push their luck should be cited under the trolling rules.