Deducting prepayment of medical expenses

[FEDUKE404]

During 2025, a client has already paid significant medical (dental) expenses, and will be able to surpass the AGI floor for same AND to itemize deductions. (In normal years, standard deduction all the way.)

There remain significant charges that will be paid for work to be performed in 2026. but likely not enough to generate a Schedule A for that year.

Is it possible for the client to PREPAY (by 12/31/2025) those expenses, or a significant portion of same, so that a larger *2025* tax deduction can occur? The dentists have already provided a summary (best estimate) of what the remaining 2026 treatment costs will be.

My question is will this action fly with the IRS? I'm sure there is a lot of "fine print" out there. And does anyone have real-world experience with this specific concept?

The client is already planning to move some 2026 contributions into 2025, and is investigating an early ("installment plan") prepayment of real property taxes on their residence.

Thanks in advance for any clarification / suggestions you might have to make this plan feasible. Client is hoping that IRS et al will "pay" around one-third of the new expenses!

FE

[TaxGuyBill]

I haven't looked up details in authoritative sources, but Publication 502 says:


"Future Medical Care

Generally, you can't include in medical expenses current payments for medical care (including medical insurance) to be provided substantially beyond the end of the year. This rule doesn't apply in situations where the future care is purchased in connection with obtaining lifetime care ..."


But I'm not sure what exactly "substantially beyond" the end of the year means.

https://www.irs.gov/publications/p502#en_US_2022_publink1000179051

[FEDUKE404]

I haven't looked up details in authoritative sources, but Publication 502 says:


"Future Medical Care

Generally, you can't include in medical expenses current payments for medical care (including medical insurance) to be provided substantially beyond the end of the year. This rule doesn't apply in situations where the future care is purchased in connection with obtaining lifetime care ..."


But I'm not sure what exactly "substantially beyond" the end of the year means.

https://www.irs.gov/publications/p502#en_US_2022_publink1000179051

Thanks. Those "details" are the sticking point. In theory, most / all of the procedures could occur before 12/31/2025, but holidays / travel / reduced office hours create some obstacles. I will pursue but may defer until 2026 and thus lose any tax benefits.
I do think I'm on firm ground for prepaying / extra donations by end of 2025. I'm awaiting response from county tax office on 2026 property taxes. They do have something called "installment plan" where upcoming property tax bills can be paid early (they just use the 2025 numbers). So long as everything is paid (2026 amount) by the due date in late summer, they are happy.

Thanks for your insight. It is appreciated!

FE

[TaxGuyBill]

This doesn't directly apply, but an Accrual taxpayer gets the deduction when "economic performance" happens. But then looking at Regulation ?1.461(d)(6)(ii), at first glance it seems to give an extra 3.5 months for "economic performance" to actually apply. As I said that doesn't directly apply to your question, but that MIGHT give a HINT for the wiggle-room for your circumstance.


(ii) A taxpayer is permitted to treat services or property as provided to the taxpayer as the taxpayer makes payment to the person providing the services or property (as defined in paragraph (g)(1)(ii) of this section), if the taxpayer can reasonably expect the person to provide the services or property within 3 1/2 months after the date of payment.