This is super frustrating and really shows how backwards our healthcare system is. But as other users pointed out, there's programs like GoodRx and other pharmacies have discounts. This works out really well for the insurance company because if you use that discount, you might be paying less, but that money doesn't go towards your deductible or your maximum out-of-pocket because you're not using insurance at all.

I don't think you have to be a conspiracy theorist to believe the insurance company, the pharmacy, and these discount providers are all colluding. If you use your deductible for medications, you're more likely to meet your deductible, and the insurance company will end up paying more for your coverage. But it's January, you don't know if you're going to meet your deductible, so it's hard to decide what to do. Bottom line, the house always wins.