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Consider the following scenario:
A user asks an anonymous question on StackExchange (on any website that allows it).

Now, the user, using they main account, puts a bounty on that question.

Can that compromise it's anonymity?

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    Well, there would be an association between the two accounts, in that they both contributed to the same question. Whether this is any more, to standard users, than an unrelated account placing a bounty on a question asked by another, is difficult to say. In theory, SE could see they both came from the same IP address (if they keep logs to that detail), but it's hard to say what they store.
    – Matthew
    Commented Jun 14, 2016 at 14:08
  • @Matthew I highly believe they store all that information. In fact, I think they use IP addresses to detect vote fraude. For example, 3-4 accounts with the same IP, upvoting answers from a specific user. Commented Jun 14, 2016 at 14:15
  • Agreed, but that would only mean that it was possible for Stack Exchange to make an inference that the two users are the same. Standard users wouldn't be able to, and it's not a certain link - consider multiple developers in the same company, whose interests are likely to be similar, and who may appear from the same external IP address.
    – Matthew
    Commented Jun 14, 2016 at 14:17

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If you mean the anonymity from the point of view that someone else can say that it was actually the user the one who asked with an anonymous user, then that's completely irrelevant. I can put a bounty in a question if I find it interesting enough and it's not receiving answers (or good answers).

If you mean anonymity in the sense that someone else can say that the user is interested in such topic, then there is really no difference whether the question was created by himself with an anonymous user or by another user.

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    That is actually a very nice point. Do you think that there's any way to pin-point said user? I really doubt that there is. Commented Jun 14, 2016 at 14:16
  • @IsmaelMiguel from the point of view of SE's admins, they could check the IP used by both users and determine if the source of the message was the same.
    – user15194
    Commented Jun 14, 2016 at 14:52

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