September 2026

The Apple Upgrade program is more complicated than it looks. I’ve seen many attempts to explain it away and I don’t think they captured the nuances.

The best way for me to understand what’s going on is to build a tool to help myself. This gives me a clear understanding of the dynamics at play in a system. As we approach the iPhone Duo purchasing frenzy, I hope it helps you decide what works for you.

Apple Upgrade Broken Down - My interactive exploration of the new Apple lease program.

After many iterations, I’m happy enough to release it into the wild. I’ll warn you though, the Apple Upgrade program is not easy to understand, and so while I did my best to make sense of it, it’s still a lot of data that will take a moment to absorb. If you want the short answer, the difference between plans is small and the levers for saving money are the obvious ones.

Simplest answer: pick the longest plan you’re willing to live with: the 24 month lease is the best if you want optionality, the 36 month carrier deal is the best if you want the absolute cheapest no matter the downsides.

We all know all the obvious stuff already, and we usually pick the worse deal anyway:

1. Cheaper phones usually beat any other optimization.
2. The longer you keep your phone, the more money you save.
3. Better trade-in values are the next best saver.
4. After the above, the best plan is the one that lets you hold on to more of your money longer.
5. Private party sale is the highest trade in per phone, but you might get burned like I have.
6. Carrier financing in the slowest cycle, but the best deal for trading in old phones that aren’t worth much.

In short, using crappier products for longer obviously saves money but at the cost of some tax on your day every day. For this reason, this tool is not about picking the cheapest phone or the cheapest upgrade cycle. This tool is here to help you understand which button to press on the iPhone Duo order page so you can stop thinking wondering if you took a bad deal.

If you’re interested in this stuff, like me, then here’s the tidbits this tool helped me figure out:

1. Both Apple Upgrade leases are maybe the best deal for people with liquid wealth that want to upgrade frequently.
2. If you can’t afford a sudden $400 charge, then you may get caught in a lease cycle trap that will be difficult to exit. That last charge to own the phone seems intentionally designed to make you want to avoid it by handing over the phone for a new lease.
3. The lease will never cost more than the cash price of the phone (but that’s not what makes it risky). The risk is overextending yourself because the payment is artificially low at first, especially when you have equity in you phone that discounts the initial payments to nearly zero. You’re using up your equity to lower the price temporarily.
4. AppleCare is really expensive. If you break your screen less than once per year, especially if you and your partner or family can distribute the cost of an occasional broken screen, then you’re much better off without AppleCare. Even a full price fix every other year is a better deal, but 2 fixes, not a good deal. This may change with the iPhone Duo, which seems hard to protect and unpleasant to put a case on.
5. If you upgrade every year, as many people do, surprisingly the best deal seems to be the 2 year lease, paid in full every year. If you pay the 2 year lease in full after 1 year, and then trade in right away you might get a reliably better deal than the lease hand-off. This is marginally better in the long run.
6. Apple’s lease trade-in, where you give your device back for free, is a luxury you pay a lot of money for. Right now a 1 year old iPhone 17 Pro Max will fetch 74% of its purchase price on trade-in. If this were an Apple Upgrade lease, I’d hand it back for 50% of the original purchase price, a $335 loss.

There’s no getting away from this: This tool is complicated. Despite my efforts, there’s some irreducible complexity here. I chose to model each month to give you a sense of your payment per month on each plan, and the months where a big charge hits, but it clutters the overall picture. Send me an issue on GitHub if you want to nerd-snipe me into fixing it some other way.

Apple Upgrade Broken Down is built to compare financing options across the same approach, but doesn’t make it super easy to compare different devices or different refresh periods. I figure it’s pretty obvious when something costs more, and buying a more expensive phone more often costs more. Anyone with the liquid wealth to pay for a full price phone repair should consider dropping AppleCare unless they know they use it. Unless you raw dog your phone every day (in which case your willingness to break your phone is a signifier of your wealth) then a good case is a better investment than AppleCare.