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Andy left a series of clues for Red to discover. But why couldn't he just tell him all that directly?

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Two words: "Plausible Deniability" –  KeyBrd Basher Aug 19 '13 at 6:22
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Andy doesn't explicitly tell Red about his plans because Red is his best friend and everybody knows this. The first person the warden wants interrogated after Andy's escape is his "thick as thieves" friend, Red. Andy did not want Red to voluntarily or involuntarily give away information or to even have a chance to compromise his escape. Hence the use of the cryptic clues. So the answer to your question is, security.

In many ways, Andy doesn't specifically tell Red that those were clues to finding him or reaching him. Red is narrating the story and he wouldn't necessarily have put two and two together to understand where Andy was escaping to. What is more likely is that Red recalls the conversation about Zihuatanejo only when he receives the postcard from Fort Hancock, Texas.

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But Red is not somebody who could be easily broken. Red is a clever person. He knows how to remain zipped up. So, if Andy doesn't tell his plans to Red for safety reasons then I think it's a plot hole or purposely added for dramatic effects (decoding a puzzle is an interesting thing to watch). My point is if you are concealing something as big as escape from your best friend then you have no right to call him even a friend. –  Ramit Aug 18 '13 at 12:12
    
Because anyways we never see Red being grilled exhaustively. Moreover, there wasn't even time because just the next day warden's corruption was exposed. –  Ramit Aug 18 '13 at 12:15
    
@Ramit Andy's last conversation with Red is something of a goodbye. He tells Red where to find him and even gives him the money to get there. What more do you want from him? The best escape plan is one that you keep to yourself. –  coleopterist Aug 18 '13 at 20:00
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that is it! He kept the plan to himself to make it foolproof. Telling Red to find money and all that, appeared like a gratitude to me, not friendship. He still is not allowing anyone to be close to him, the same reason why he believes his wife left him. So redemption are we talking about? –  Ramit Aug 19 '13 at 5:29
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He says if he's ever freed or escapes, he'd like to go to Zihuatanejo, a beach town on the Pacific coast of Mexico. He also tells Red how he got engaged. He and his future wife went up to a farm in Buxton, Maine, to a large oak tree at the end of a stone wall. The two made love under the tree, after which he proposed to her. He tells Red that, if he should ever be paroled, he should look for that field, and that oak tree. There, under a large black volcanic rock that would look out of place, Andy has buried a box that he wants Red to have. Andy refuses to reveal what might be in that box. The Shawshank Redemption - IMDb synopsis

So we know that Andy did tell Red where he was going, even though it was in the passing. Though Red might not have known it at that time. He never even told Red he was escaping. All he ever said to Red was - "find that Box".

I believe that this was a test of friendship for Red. If he would indeed find the box, he could join Andy. If not, Red probably would have no clue where Andy might have gone. So if Red went searching for the box, then he was a true friend. Because he had carried out his word given to Andy. And Andy in turn helped his friend reach him by providing money and instructions to reach Mexico.

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After nearly 20 years of togetherness, you still need to test your friend? It's not done. –  Ramit Aug 18 '13 at 16:16
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it's done when you leave the prison... you're out in a strange world. And it depends on the person whether they want to pursue the friendship or not. –  kicker86 Aug 18 '13 at 16:27
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maybe you take the term test in a different light. It simply means to go through some motions... –  kicker86 Aug 18 '13 at 16:28
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