This would help you offer all the products from a specific category at a discount when the customer purchases at least any 1 from the same category.

That is 1 quantity of 1 product from the category will be charged at full price. The subsequent quantities of the same product or other products would be offered at 50% discount.

NOTE: This discount rule is only available in the WooCommerce Discount Rules PRO version

Start creating the rule buy going to WooCommerce -> Woo Discount Rules -> Price Rules -> Add a rule.

General Tab

Make sure you choose the "Quantity based discount / BOGO deals method"

Conditions Tab

Set the Apply To as "Specific Categories" and choose the category.
Make sure to check the box to count items cumulatively as seen in the screenshot

Discount Tab 

You need to add multiple ranges. Because when customer purchases 2 quantities, he is eligible for a 50% discount for only 1 quantity.

I have added ranges up to 4. But you can add up to 10 or 20 depending on your customer's purchase behaviour.

Adjustment type should be: Product discount
Apply To should be: More than one cheapest from selected category (This will ensure that the highest priced product is charged at full price. Discount applies only on the cheapest priced ones)

Here is how it would look at the cart.

As you can see, the highest priced item would be charged in full price.

If you have any further questions, feel free to reach out to us via the Live Chat.

Frequently Asked Questions

1. How to add more categories
Example: Buy any 1 product from Category A and B, and get discount on other items from these two categories.

Just choose both the categories in the Conditions tab and also in the discount tab.

2. How to provide "Buy any 1 item from Category A and get any cheapest from Category B

Checkout this detailed guide
Here is the guide detailing the changes in naming conventions since 1.7.0 version.

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