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Buy now & saveI look at what you're trying to achieve, and this is not the experience that I want you to have, @aiannarelli.
You're correct about what you have bumped when setting up customers and overrides to a price rule. I also get disappointed when the feature I operate doesn't coincide with the expectation that I want to experience.
In the meantime, I suggest submitting feedback to our engineers to notify them about this. In that manner, they'll make sure to fix this in future updates and won't have to include the customers manually and use the Search field without the system removing other customers/jobs/items that you added recently.
Here's how:
I'm also sharing this article for more details: Use Advanced Pricing. This includes how to put an adjustable discount for items as your customers buy them to a specific quantity.
If you have other concerns to add or need help with using the Advanced Pricing in QuickBooks, feel free to let us know. I'm looking forward to helping you more. Stay safe and well!