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I'd like an account that isn't associated to my real name, but I really don't want to bother using different connections for the accounts. Of course I wouldn't let those two accounts communicate, e.g. through voting. It would still be obvious that I owned both accounts to a moderator who investigated them.

Can I have such a setup without fearing merging from an overzealous moderator?

If someone decided to wrongfully merge those accounts, would there be a way to dissociate the merged questions from my original account?

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If you keep your two accounts completely separate, and never upvote/comment/answer in the same question, you shouldn't have to worry. Of course, if you screw up and get merged, TS. – Won't Jun 24 '11 at 13:30
@Won't: Or if someone else screws up and I get merged. – user157130 Jun 24 '11 at 13:53
@Tim: Nope. Since having multiple accounts isn't generally allowed and there is no guarantee you won't be merged, you can't claim that your accounts got merged because someone else "screwed up." You have no reasonable expectation, to steal a legal term, that your accounts won't get merged. – Won't Jun 24 '11 at 13:58
@Won't: Since you answer my question, maybe that should be an answer? (I was under the impression that it was allowed, though.) – user157130 Jun 24 '11 at 14:00
@Tim: I think Chris covers this fine. Think of the ability to have multiple accounts not as a bug but as a feature. It isn't supported directly, can be considered a failure in the system, but is left in a gray area. There is no official support for allowing individuals to run multiple accounts. You can do this, yes, but more because it is nearly impossible to enforce one person = one account. – Won't Jun 24 '11 at 16:53
possible duplicate of Explicit support for multiple accounts – Lance Roberts Jun 24 '11 at 17:55

To answer the last part of your question:

A merge (of anything, not just a user) is a one way operation. Once it's done it can't be undone.

Given that most second accounts are either created by accident by unregistered users or deliberately by people wanting to game the system the natural reaction of moderators on finding them is to want to merge.

Therefore, as there's always the possibility that if you did create a second account it would be merged with your main account, you would need to think long and hard before posting.

You could post as an unregistered users using incognito mode/private browsing. You'd have to keep separate bookmarks of your questions and be careful with your cookies. However, this account may still be merged.

So to answer your main question:

While you can have two independent accounts there will always be the risk that an "overzealous" moderator could merge them. To quote Jeff

what legitimate reason would you need for multiple accounts?

and this would never be a "wrongful" merge.

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So basically, I'd have to game the system (proxies, tunnels) to avoid getting merged for gaming the system? =/ – user157130 Jun 24 '11 at 11:36
Isn't there a precedent of people having multiple accounts peacefully co-existing so long as there was no interaction between the accounts? In other words, so long as account_A did not vote on, answer, or comment on anything by account_B, and vice versa, that it would be okay? – Al E. Jun 24 '11 at 12:20
This answer from Jeff is germane to this. – Al E. Jun 24 '11 at 12:21
@Al Everett - yes, but I was addressing the point about merging being non-recoverable and that there will always be a risk of merging. – ChrisF Jun 24 '11 at 12:22

You can, provided the two accounts have nothing in common.

The IP address match is not really an issue, it's the emails or openids matching that will trip you up -- and intentionally, as ChrisF points out because 99% of the time when this happens it's users who accidentally do it.

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