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Model A1288 / 8, 16, or 32 GB capacity

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How do you replace the headphone jack?

I took out the screws but it still doesn't come out and I don't know what it is holding it back

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iFixit does not have a repair guide for this particular repair for this model, but I believe this teardown might be of some assistance to you:

iPod Touch 2nd Generation Teardown

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+ good, but markus was better

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the headphone jack is soldered to the logic board (5 soldering "points" - on the left side of the headphone jack)

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You must have a mean library of photos Markus. LOL +

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+ maj, you forgot the +, nice photo

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sure, gazillions of photos

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you have to take off the digitizer and unscrew the two screws by the headphone jack and replace it...im pretty sure at least

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madmarcusd will be eternally grateful.
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