To my brothers on T I know this is gonna be harder for you so please listen up:
First, if your doctor is open to it, ask for the 2000mg/10ml vial, you'll need to be careful to keep it clean and free of contamination from the stopper, but the expiration dates will typically be a year plus. Please specify the 10ml vial and not a three month supply, the difference is minimal but important.
Next, have it sent to a busy, understaffed CVS (most of them are busy and understaffed). If your insurance doesn't cover CVS use GoodRx, at time of writing it should be about $50. Our system by default makes us mark the 10ml vial as a 28 day supply regardless of the dosage because we cannot guarantee a beyond use date beyond that (as I said, non-zero chance of contamination, use a 90 degree angle and a alcohol pad every time and you'll be fine). Only the most stickler of pharmacists or technicians are going to bother changing it - if they even know the system workaround to bypass it.
Then, come to refill it the next month. If they marked the first fill as 28 day supply (you can see on your label in the lower right near the price) it will process without any red flags in the system and will again will likely slip by all but the most stickler of pharmacists and techs. If they marked it as something longer just explain that your doctor told you to discard the vial after 28 days per USP guidelines and so you were a good boy and already threw it out, this should work against all but the biggest douchebag of a pharmacist. If that fails and your doctor is cooperative, have them call the pharmacy and authorize an early fill - if that doesn't work try another pharmacy.
If all goes well you'll probably be able to fill two to three vials in a row before anyone starts to question things.
I cannot speak for other pharmacies, but in general retail pharmacy is kind of a shit show right now so a busy store in another chain is also probably going to just go by USP even if their instincts or morals tell them to be jerks about it.
If anyone has any questions or if you need advice on a situation I didn't cover please DM me anytime, or hell send me an anon ask if you're shy. If anyone's insurance requires a non-CVS pharmacy and you can't afford the $50 let me know and I can find a tech at another pharmacy to see if they have any advice that would be relevant to their chain.
To my transfemme sisters, you've got it a little easier. Have your doc send your meds with a 12 month supply to a pharmacy you don't typically use, use GoodRx if you have to, none of the usual drugs in a transfemmes HRT regiment should be extremely expensive. Tell them you're going out of the country in a week or two and would like to purchase the entire year's supply at once. A year's supply of 2mg estradiol tabs taken four times daily (the max dose I've ever seen) is $75 on GoodRx at CVS right now. They'll probably need to order more tabs in but again only the biggest stickers are gonna question it. (You can also send to your usual pharmacy if you don't take any other meds, but I recommend not returning for at least a year just to be on the safe side. It's not illegal, but again you could run into some stickler pharmacist who calls your bluff and refuses further fills or tattles to your doctor or something.)
Again, please please please don't hesitate to send me DMs or asks if you have any questions or need specific advice.