The benefits portal is open on your phone between pages, the enrollment deadline is close, and the screen wants three answers: which medical tier, whether to fund an HSA, and whether to add anything beyond the program’s group disability plan. It is easy to click through in four minutes and keep last year’s choices. On a resident stipend, those clicks are some of the biggest money decisions you make all year, which is why benefits sit next to pay in our guide to surviving residency. This post takes the three choices in the order you will meet them. It is general education, not tax, insurance or financial advice.
Step 1: Price the family tier against the outside options
A PGY-1 who is the only earner for a family of four described this exact problem on Reddit recently: the program’s family plan costs several hundred dollars a month, and they wanted to know what cheaper options exist. Before you accept that number, collect three figures: your monthly premium for each tier, the deductible, and the out-of-pocket maximum. Then check the alternatives that are open right now.
Open enrollment for 2027 Marketplace coverage started November 1 in most states, and the subsidy rules have changed. According to KFF’s 2027 open enrollment preview, the enhanced premium tax credits expired in 2026, and households above 400% of the federal poverty level no longer qualify for any premium tax credit. A large single-income household on a resident salary may still fall under that line, so enter your real household size and income on your state’s marketplace site instead of assuming you’re priced out.
Then ask the benefits office two questions in writing: “Does the program’s plan count as affordable coverage for my spouse and children under ACA rules?” and “Is there a lower-premium tier or a high-deductible option for dependents only?” If your children might qualify for your state’s CHIP program, ask the state Medicaid office directly. The answers decide whether you’re comparing one plan or three.
Step 2: Fund the HSA without tripping the testing period
If you pick a high-deductible plan, the IRS limits are already set. The 2026 and 2027 figures are $4,400 self-only and $8,750 family for 2026, rising to $4,500 and $9,000 for 2027. To qualify, the plan’s deductible must be at least $1,700 self-only or $3,400 family in 2026, and $1,750 or $3,500 in 2027.
The trap is for anyone whose next program sits somewhere else. The IRS last-month rule treats you as eligible for the whole year if you’re HSA-eligible on December 1. That lets you contribute the full annual amount even if your high-deductible coverage started in July. The catch is the testing period: you have to stay eligible from that December through the end of the following year. If you don’t, the extra contributions become taxable income, plus a 10% additional tax, as this explainer of the rule lays out.
Run it with a transitional-year resident whose high-deductible coverage began July 1, 2026, and whose categorical program next July may not offer an HSA. Prorated, the 2026 self-only limit is six months of $4,400, or $2,200. The last-month rule would allow $4,400, but leaving high-deductible coverage in July 2027 fails the testing period, and the extra $2,200 is taxed with the penalty on top. If you’re moving programs in the next 13 months and don’t know the new plan, contribute the prorated amount. For 2027, your limit is the months you’re actually covered, so six months covered means $2,250 self-only.
Ask your incoming program now: “Does the house staff plan include an HSA-eligible option, and when does coverage start?” If you already went over, a tax preparer can tell you how to withdraw the excess before you file.
Step 3: Decide on disability coverage while it is still cheap to qualify
A PGY-3 looking at attending contracts asked whether disability coverage really gets more expensive after graduation. The bigger issue is qualifying, not just price. Many programs have guaranteed standard issue (GSI) arrangements with individual disability carriers. As this Medical Economics piece describes them, GSI policies need no medical exam and no health history, they’re own-occupation and non-cancellable, and the window closes permanently when training ends. That article puts resident discounts at 10% to 30%. Another broker’s summary says 20% to 40%. Both sources sell policies, so treat the ranges as rough and get quotes.
Two details are easy to miss. A future increase rider bought during training can let you raise the monthly benefit later without new medical underwriting; the Medical Economics piece cites up to $15,000 a month. And applying for a fully underwritten policy first can cost you GSI access, so find out about GSI before you fill out any carrier’s health questionnaire.
Ask the GME office: “Do we have a GSI disability program, with which carrier, what is the benefit cap, and does it require own-occupation coverage in my specialty?” Then have an independent broker quote at least two carriers, and read the definition of disability yourself. Group coverage belongs to the employer that sponsors it. An individual policy you own goes with you to the first contract and every job after it.
What to have done before the deadline
By the time you hit submit, you should know three numbers: your annual premium cost per tier, your prorated HSA limit, and the monthly benefit you would get on an individual disability policy. If you can’t name all three, the four-minute click-through is still making the decision for you. Book an hour with a tax advisor if you’ve already put too much into an HSA, and talk to an independent disability broker before you sign an attending contract that would close your GSI window.