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I'm wanting to set up a promotion that is 25% off one item only from specific categories.

How would I do this so that the cart applies the discount to only one item, preferably the highest priced item in the cart?

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Unfortunately you can't achieve this with default Magento rules.

You have 2 way to do this discount. First way - write discount code by yourself.

How we perform this action at our Special Promotions extension -

1) Put observer to <salesrule_validator_process> event

2) Sort all items from address

3) Give discount to the expensive one item

Second way - purchase one of hundred extension which provide this functionality.

Feel free to ask any questions.

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