You're the Dread Pirate Roberts (Westley), and you've crossed the Sea, climbed the Cliffs of Insanity, battled a Spaniard fencer and a Turkish wrestler, and tracked your Lady Love to near the Fire Swamp.
There you find Buttercup, blindfolded, with a knife at her throat. A Sicilian man holds the knife, and before them is set a picnic.

He greets you with an accusatory "You're trying to kidnap what I've rightfully stolen."

You think for a moment, then reply, "Perhaps an arrangement can be reached, or we are at an impasse."

"I'm afraid we are: I can't compete with you physically, and you're no match for my brains."

"Really? In that case, I challenge you to a battle of wits."

"For the princess? To the death? I Accept."

You reach into your cloak, and pull out a small pouch, handing it to the man. "Inhale, but do not touch. What you will not smell is called Iocaine powder. It is odorless, tasteless, dissolves instantly in liquid, and is among the more deadlier poisons known to man."

The man does as he's told, then uncorks the wine. He turns around, blocking his activities with his body, after a short time, he turns back, placing a full drinking vessel in front of himself, and one in front of you. In the centre of the table he places a slip of paper with cryptic writing on it.

"The battle of wits has begun. It ends when you decide and we both drink, and find out who is right, and who is dead. I dearly hope you don't suffer from triskaidekaphobia, or you may fall at the first hurdle."

IBygdDgCYMSwdts boQdBXwBNh caHnp2rQMnzaiWsY'S9bgjcIWsdtgtc1Gbkmw5 o
od 2bx2wVNzian2tcGs5MhjdnGitrgQIsjdACccsouTgHekCwBoshIsGcNSwBMhnImHttHl
BMmjIcHeN 6VIhDbIFednyyb0GIY2wNiytboGIRGw9MpvI HulHkdNsDYaGtZr6RayDLc2bthy com
hTa W 4m1Ba0DbkWtgyguIwmIImwFhgoDnHb5GwQMuaZuQiR25ZMgTItn'ptqlcvTcYH JdUyIzCbIGwdyw Z GbB2w9Mooaemtp2owMpzZuCvhox4bgjckW Bek ZgGdc2w4c2ndsXaR2w9Mgoc GalWy9MuDRuisRv55c1jZQGlBised02bkWwVdptI 2b9GxQMh Z HyNy2QMgDdbHaVo4BagTdIGeUtmuIoGccGwgau b.HaRmwhOgtItGAZX5VOlDa AhtrsMbhDIQXm0i6eagnYIGwMeKsI WbM2wdMg,R HyF3ggNvTb XtpojdagTYU2ihajuauHZImw4n3bZ mIlmwxMg IlnlcGh9OlzdtHeIogdeyDdkGhd!gnaviIQCwhirIRgHYBHwBMlsa'G lmLdMpDI CvZfhxcoTbQGbBepoelWYAiwxau YridFXwBOptarW BChQNmDbtGept0wYgDcUmlIdyhcgiakmwUegoaiWY4Gw9Mh du2s9mgUMuDDo3b9 0VDgTdAQfIlowYjQdkCwp geLo3Yo2wBMCwddCrlXwFMvDci2 BlyVMzDZQnttt1dczjIciwgsohZ?XZQGwBNg.IeCTYSwdOtDZAH BmuBMpDZUHlpd29IojdUSwVlroY3AZkmw4MoocsWL0SwVOgjIwmehCKBMuTTkH 9,jBT3jLgmwRmo bhGbYiwVM4eIb3IR3wAM2Db GyZGrVMNDZMHth mNIszCYXwdoxtdsHZEkwIMo dhiZVCwkOgTIr2eBXpBNnDZkGeh qZarzbU2wZg1wdlHbISw8MvicaHcNmwBMgDas3yZiw9NuTaAHtV,xBa3TbYWxles ZtGIQ3w4MordsCYxHwQMgjd mo4WjRMgDYISmg g4eojYIW

Note: Computer usage is recommended, but not required. And, as always, show your work.

  • $\begingroup$ Ah, The Princess Bride. I really enjoyed that movie. $\endgroup$
    – Ivanhoe
    Sep 7, 2016 at 12:58
  • $\begingroup$ What's the question? "Who wins", or "what should your strategy be", or just "what does the message say"? $\endgroup$ Sep 7, 2016 at 13:15
  • 1
    $\begingroup$ @randal'thor 'It ends when you decide and we both drink, and find out who is right, and who is dead.' The question: Which goblet do you drink from? Of course, being puzzling, showing your work is also required. $\endgroup$
    – Sconibulus
    Sep 7, 2016 at 13:17
  • 1
    $\begingroup$ If this had [Lateral-Thinking] I would say "pick whichever cup you like, you're the Dread Pirate Roberts, you've built an immunity to Iocaine powder over the years." $\endgroup$
    – dcfyj
    Sep 7, 2016 at 13:27
  • 2
    $\begingroup$ @dcfyj Not any more - check out MOehm's answer! $\endgroup$ Sep 7, 2016 at 13:36

2 Answers 2


Continuing M Oehm's work: if we continue until we have used the whole message, base64-decoding what comes after the text he posted yields:

Now, a clever man would put the poison into his own goblet, because he would know that only a great fool would reach for what he was given.
I'm not a great fool, and poisoned the goblet in front of me. Never go in against a Sicilian when Death is on the line!
Brx duh txlwh fohyhu lqghhg, wr kdyh frph vr idu.
Exw wkh nhb wr wkh zkroh hqwhusulvh lv wkh srlvrq.
Tfhdtdl uflkz zcfr Dfiajrkoh, ud vahcovfv jtvqd.
Rsg Lkzlizrpu tj jqeyywcx vliacjg hyaz tqotcyrqv.
Ldk uihsphlcx klll se ddjffjnyp hldrsovhdyns hyaz Kqaab.

The block of garbled letters does not appear to be English under a simple substitution cipher. (More precisely: I fed it to quipqiup and it didn't produce anything even slightly plausible-looking.) I haven't tried anything more complicated.

... Two people have noted in comments that the first two lines are Caesar-ciphered (I thought they had that look and was surprised quipqiup didn't do anything more helpful!) and yield

You are quite clever indeed, to have come so far. But the key to the whole enterprise is the poison.

suggesting that either the remainder, or the remainder after unCaesaring (my guess is the latter) wants Vigenere-decoding with "iocaine" or "poison" or something as key. It turns out that using "iocainepowder" as key for Vigenere-decoding what you get after uncaesaring yields

iocaine comes from australia, as everyone knows. and australia is entirely peopled with criminals. and criminals have an exclusive relationship with truth.

so it looks as if we are going to need to attack those digits to find anything actually useful. Unless

"criminals have an exclusive relationship with truth" just means "criminals always lie", in which case we need to take everything Vizzini says as a lie. (Literally everything? Hmm.) That would suggest e.g. "I am a great fool, and didn't poison the goblet in front of me" meaning we should take his goblet. But those digits may yet prove to be significant digits...

The digits seem to want to be in groups of three, yielding the numbers

24 29 26 31 72 54 23 29 29 6 48 82 12 27 29 117 82 52 84 10 49 19 7 85 98 6 85 16 2 72 60 22 7 19 16 39 4 2 84 15 39 4 85 0 4 45 29 3 19 0 122

but it's not yet clear to me what we should do with those. (Exclusive-or them with something?)

Well, XORing those with the ASCII codes of "TruthTruthTruth..." yields

"Look behind you! A bear!\nR'ev hdrgxsvw gsv tlyovgh."

so we seem to have a rather small residue of cryptic nonsense to deal with now.

The letter counts match

I've switched the goblets.

and indeed it turns out that A->Z, B->Y etc. turns the one into the other.

OK, so how do we put all this together? Well, whether or not we take the "exclusive relationship with Truth" to apply to Vizzini's statements, he has claimed

that he didn't poison his own goblet, and that he switched them

and if we assume the two bits of this are either both true or both false (and that he didn't poison them both) then

the goblet that is now not his should be safe.

  • 1
    $\begingroup$ If you ROT-23 the next bit it decrypts another 2 lines $\endgroup$
    – Wu33o
    Sep 7, 2016 at 13:47
  • $\begingroup$ The first two lines are Caesar: "You are quite clever indeed, to have come so far. But the key to the whole enterprise is the poison." Maybe we should decode he lines individually. $\endgroup$
    – M Oehm
    Sep 7, 2016 at 13:47
  • $\begingroup$ The next line has a capital word with 9 letters, which may be Buttercup. If so, it's not a simple substitution cipher, because the "tt" is rendered as "ia". I've tried Vigenere with the key "poison" as suggested in the previous line, but got nothing. $\endgroup$
    – M Oehm
    Sep 7, 2016 at 13:52
  • 2
    $\begingroup$ c2.com/cgi/wiki?BattleOfWits the script for this portion of the movie. Since the puzzle seems to so far follow it $\endgroup$
    – Areeb
    Sep 7, 2016 at 14:02
  • 1
    $\begingroup$ Secret answer: I drink away. I spent a lifetime building up a resistance to iocaine. $\endgroup$
    – Cloud
    Sep 8, 2016 at 2:06

Partial answer for the "first hurdle":

The man mentions triskaidekaphobia, the fear of the number 13. Taking every 13th letter from the note, we get a text that starts with "It is", which looks promising.

Remove the line breaks from the message and continue. When you reach the end of the message, start over, but begin at the second, then at the fourth letter. After that, the message is gibberish. The intelligible part reads:

It is inconceivable that you could beat me, in this battle of wits.Allow me to register my astonishment that you'd even sit at this table!I've redoubled the dose, by the way, so don't trust your immunity to save you.Are you long for this world?

The text is rendered like this, without space after the punctuation marks. The rest of the message may also be of importance, but I've left it out for the moment. And I won't be any help with anything regarding the Princess Bride, I'm afraid.


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