I fly often and have never had an issue going through TSA. I casually inform the agent that I have an medication Travel Cooler pack case and ask if I should remove it from my backpack. 100% of the time they respond by saying “they will be able to see it and there’s an issue they’ll let me know”. So far, never an issue. I’ve flown with vials, pens, syringes (both disposable and pen needles) all at once. I don’t think they care about my meds. Just my experience with TSA.