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Do you have to serve two jail sentences? For example, you go to jail the first time and use your "Get out of jail free" card, and then go right back to jail for another sentence without rolling the dice.

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    Highly related/duplicate: boardgames.stackexchange.com/q/38845 – Jan Mar 28 at 13:48
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    Although this question has already been answered correctly, if you want to have some fun with this I suggest that it is in the scope of the rules to pretend like you didn't remember this is your third roll of doubles, start moving, then land on "go to jail" and exclaim, "OH NO! I LANDED ON GO TO JAIL!" as you move your token to the jail. This would work especially well if some of the other players catch you on it being your third roll of doubles and are trying to explain it to you while you ignore them and move your token anyway. – Michael Mar 28 at 17:04
  • @Jan I agree that these are about the same thing, but neither is a good duplicate candidate for the other. I've tried to create a canonical question to merge the two: boardgames.stackexchange.com/q/45706/9999 – Zags Mar 29 at 22:08
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You go to jail directly on rolling the third double, so there’s no opportunity to land on “go to jail”.

  • This answer, as well as the other answer given later on, addresses the game mechanics. It is explicitly stated in the rules that property cannot be purchased, and it sort of follows that rent cannot be collected, either. I don't think I have ever tried moving my piece according to the dice value before going to jail when rolling doubles a third time in a row. – Iktys Mar 27 at 13:10
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    @Iktys "and it sort of follows that rent cannot be collected" No it doesn't. That's one of the most often debunked myths. – Joseph Sible-Reinstate Monica Mar 27 at 23:37
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    @Joseph, I believe what Iktys meant is that if your third doubles would cause you to land on someone else’s property, the other player doesn’t get to collect that rent before you go to jail. – prl Mar 28 at 4:13
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    I mean, at the space you would have landed on with the third doubles, you don't pay rent. – Iktys Mar 28 at 6:19
  • There's no such thing as "the space you would have landed on with the third doubles." When you roll the third set of doubles, you go immediately to jail. There's no point in counting spaces to see where you "would have landed." – Kyralessa Apr 5 at 20:43
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You're thinking about this too much in terms of real-life prison sentences, and too little as game mechanics. "Jail" is simply a location on the board, associated with a few specific rules, but none of those rules suggest that there would be "Jail Time" stacking up. Instead, you are either in Jail, or not.

Furthermore, upon rolling doubles a third time, you are directly placed in Jail without executing your movement anyway:

When doubles are rolled, the player resolves the roll as normal (including purchase, renting or passing "GO"), but rolls the dice again for another turn (you have to keep going). The player moves forward as directed by the dice, and if this is also doubles, rolls again. If the third dice roll is doubles, the player cannot buy property, and is instead moved directly to jail. [source]

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    " "Jail" is simply a location on the board, associated with a few specific rules," Ooooooh... suddenly a lot of things regarding life and politics are more clear to me. – Michael Mar 28 at 17:06
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    Where is your quotation from? – EleventhDoctor Mar 29 at 16:22
  • @EleventhDoctor I hadn't realized I forgot the source link - added! – TheThirdMan Mar 29 at 20:41

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