How to enroll for 2027: step by step

From November 1, when you log in to your Benefits Portal you'll go straight to your 2027 enrollment. It takes about 5 minutes if you're renewing, or about 10 if it's your first time. You can stop anytime: when you log back in, you'll pick up where you left off.

The progress bar at the top shows where you are: Your details → Pick your plan → Send us proof → Where to send it → Onboarding complete.

Before you start: your timeline

Now – Dec 15: buy your plan and send us the proof.
Usually 1–2 days later: your employer reviews and approves your request.
4–5 business days after that: your reimbursement lands in your bank account.
Jan 1: your coverage starts.

Some states give you more time. See the Open Enrollment 2027 State FAQ.

Step 1: Your details

Confirm three short sections, then click Looks good to me!

About you: your name, phone number, date of birth, sex and whether you smoke.
Who needs health plan coverage?: choose Just me or My family (me + others), and add your spouse or other dependents. If your employer offers more for dependents, you'll see your allowance go up as you add people.
Where do you live?: your home ZIP code decides which plans you can buy.

Next, you may see an optional step to estimate whether you qualify for a marketplace subsidy. You can click Skip for now.

Step 2: Pick your plan

You'll see Recommended plans where you live, plus how many days you have left to enroll. Every price shows your estimated cost after your employer's reimbursement.

Plan cards: we show the best plan in each coverage level first. Each card shows what you pay the insurance company, what's Reimbursed, and Your cost, plus the deductible and the most you'd pay in a year. Click View plan details for more.
Compare: tick Compare on up to 4 plans, then click Compare side by side in the bar at the bottom of the page. You can download the comparison as a spreadsheet.
Want more choices? Click Browse all to see every plan sold where you live. There are two ways to shop:
- Shop direct plans (direct to the insurance company): about 10 minutes to apply, no marketplace account or ID checks, and coverage starts on time.
- Shop marketplace plans (HealthCare.gov or your state's marketplace): more networks to filter by doctor or drug, and tax credits if you qualify, but a longer application with ID checks.
Check your doctors and prescriptions. The recommended plans aren't filtered by doctor or medication. Use View formulary on a plan, or check with the insurance company before you buy.

Already enrolled, or covered another way?

At the top of the page, click I already enrolled in a plan, then choose how you're covered for 2027:

I purchased a marketplace plan: an individual plan you bought yourself, directly from an insurance company or on the marketplace. You'll go straight to sending us your proof (Step 3).
I'm on someone else's plan: a spouse's, partner's or parent's employer plan. These don't qualify, so you'll waive your allowance.

Buying your plan

Click Enroll on the plan you want. The plan page shows What you get, What you pay and Your real cost, and walks you through three steps:

Apply with the insurance company. Depending on the plan, you'll see one or both of these buttons:
- Apply in StretchDollar (some plans): fill in and submit the application without leaving StretchDollar. Your reimbursement request is created for you when you submit, so you can skip Step 3.
- Buy plan: the insurance company's application opens in a new tab, already filled in with your details. Finish and submit it there.
Pay the insurance company your full first premium. Your coverage isn't active until that first payment clears, so do it the same day if you can. If you applied in StretchDollar, use the Pay [insurance company] now button on your application summary.
Come back and send us your proof. If you clicked Buy plan, come back to StretchDollar and click Submit proof of coverage. Your confirmation email or a screenshot of your member portal is enough. This is the step people most often forget, and without it we can't reimburse you.

Plans bought directly from an insurance company have their own cutoff: apply by December 15 to be covered on January 1.

While you apply, you can also name StretchDollar as your broker. It costs you nothing, and we can step in with the insurance company if anything goes wrong with a claim or bill.

Step 3: Send us proof

Upload your proof of coverage (a photo or PDF of your invoice or enrollment confirmation). Check the plan details we read from it, answer the short questions about your plan and how you pay for it, tick the confirmations, and click Submit. Not sure what counts? See Proof of coverage: What do I need to submit?

Step 4: Where to send it

Connect the bank account where you want your reimbursements. If you've connected one before, just click That's still right.

Step 5: Onboarding complete

That's it! Once your employer approves, your first deposit lands 4–5 business days later, then every month automatically. From here you can also add dental or vision with whatever's left of your allowance, or click Go to my dashboard.

Don't want the benefit this year?

Choose I want to waive my allowance, pick a reason, and click Confirm waive. Waiving cancels your reimbursements for the year. If you're waiving because you're using a marketplace subsidy, you'll be asked to upload proof of that coverage. See How do I change my benefit selection?

Questions? Email us at [email protected].