Before you touch the enrollment portal

Find your actual enrollment deadlineMissing it can mean defaulting into a plan you didn't choose, or losing coverage entirely, with no fix until next year.
Pull last year's medical, dental, and prescription billsYour actual usage matters more than the plan's marketing.
List every prescription, ongoing treatment, and planned procedure for the coming yearSurgery, pregnancy, orthodontia — plan for what's actually coming.
Check whether your doctors and hospitals are in-network for each plan optionNetworks can change yearly even under the same insurer, not just under a new plan name.
Note any life changes since last yearMarriage, new baby, dependent turning 26, spouse's new job all affect what coverage makes sense.
Compare both companies' plans side by side before assuming yours is better if spouse has employer coverage

Choosing your health plan

Compare total cost, not just the premiumAdd premium × 12 to your expected deductible and copays/coinsurance for a realistic yearly cost.
Confirm whether a plan is HSA-eligible (a high-deductible health plan) before committing money to an HSAContributing to an HSA while enrolled in a non-qualifying plan can create a tax problem.
Check the out-of-pocket maximum for each planThis is your worst-case cost in a bad year, and it's often more revealing than the deductible.
Look up whether your specific medications are on the plan's drug formulary and what tier they're in
Weight cost predictability (lower deductible) over a cheap premium if planning pregnancy or major procedure
Consider a high-deductible plan paired with an HSA if generally healthyOften the cheaper long-run choice if you're generally healthy and rarely see doctors.

Decide between an HSA and a Health FSAYou generally can't have both at the same time (a "limited purpose" FSA for dental/vision is the usual exception), so this locks in your plan choice too.
Check this year's IRS contribution limit for HSA or FSA before setting your amountThese caps change annually and contributing over the limit triggers a tax penalty.
Set your FSA amount conservativelyMost FSAs are still "use it or lose it," with at most a small carryover or short grace period, and unused money is forfeited.
Confirm whether your employer's FSA carries over a limited dollar amount, offers a grace period, or neitherThis changes how aggressively you should estimate spending.
Look at a Dependent Care FSA separately from your medical FSA if kids in daycare or after school careIt's a different account with its own limit.
Remember HSA funds roll over indefinitely and stay yours even if you change jobsUnlike an FSA.

Check if you're being auto-enrolled in a "no cost" flat amount of employer-paid life insurance, then decide if you need to buy moreThe free amount (often 1x salary) is rarely enough if you have dependents.
Compare short-term and long-term disability coverageThis replaces income if you can't work, and many people skip it without realizing how thin their savings cushion is.
Check if it requires "evidence of insurability" (a health questionnaire) if buying supplemental life or disability insurance for the first timeWaiting until you need it can mean denial.
Note whether disability premiums are paid pre-tax or post-taxPre-tax premiums make the eventual benefit payout taxable, which matters if you ever have to use it.
Review accident, critical illness, or hospital indemnity add-ons only if you already have a reason to expect higher-than-average medical risk if add ons offeredOtherwise they're usually a low-value add.

Set your 401(k) or 403(b) contribution rate high enough to get the full employer matchLeaving match money on the table is leaving free money on the table, permanently.
Check this year's IRS 401(k) contribution limit if you're aiming to max outEspecially the higher "catch-up" limit if you're 50 or older.
Decide pre-tax vs. Roth based on whether you expect your tax rate to be higher now or in retirement if roth 401k option offered
Review commuter/transit or parking pre-tax benefit elections if your employer offers themThese usually need re-enrolling each year too.
Look at legal or identity-theft protection plans only if you have a specific ongoing need if legal or identity theft plans offeredOtherwise these are low priority.

Submit your elections before the deadline and get a confirmation screen, email, or printoutVerbal or in-progress selections don't count if the system times out.
Double-check dependents are listed correctly on health and life insurance electionsA misspelled name or missing dependent can delay claims later.
Update your beneficiary designations on life insurance and retirement accountsThese override your will, so an outdated ex-spouse or old address can misdirect a payout.
Save a copy of your final elections and the plan summary documents (SPD) somewhere you can find them mid-yearNot just in the portal.
Contact HR immediately if you missed the deadline if missed deadlineSome plans allow a short correction window, but most don't once the deadline passes.