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I am going to split this into players A and B to simplify my question;(placement rules applied)

Player A has a road which is 7 in length and has the Longest Road tile,

Player B has a road which is 5 in length (second longest road),

Player B builds a settlement mid-way along Player A's road resulting in Player A now having two roads - a length of 4 and a length of 3.

Does Player A surrender the Longest Road card as his previous longest road no longer exists? (and as a result Player B obtains this honour)

Also, if (in the above example) Players B and C had a road less than 5, would the Longest Road card return to the bank?

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marked as duplicate by user1873, Colin D, unor, Paul Marshall, Gregor Aug 6 '13 at 18:23

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up vote 4 down vote accepted

Yes and Yes. In the rules it states that if the longest road is split, then you re-evaluate who has the longest road. If no-one qualifies (or it is now a tie) it is returned to the bank.

Building a settlement to split someone's longest road is a key tactic in Settlers, which can be prevented by the player building extra roads and/or settlements to protect the vulnerable spots, but that obviously slows down their road building.

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If this action results in a tie -and- the current holder is one of those tied, I'd expect it to remain with the current holder. This being equivalent to a second player adding a road section to match the length of your existing 'longest road'. You need to own an unambiguous Longest Road to gain the card. –  Cheeseminer Aug 7 '13 at 14:19
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