2027 Open Enrollment: What Agents Need to Know
Here's a quick summary of the most common questions that come up during Open Enrollment.
When is Open Enrollment?
For most people, Open Enrollment runs November 1 – December 15, 2026 for coverage starting January 1, 2027. Some states have different deadlines — check the Open Enrollment Overview for your state's exact dates.
How do I get into my StretchDollar Benefits Portal? I can't remember my password.
No worries — just visit the log in page and choose "forgot password." You'll receive a new one right away. You can always find the log in button on the StretchDollar.com homepage.
How do I find my 2027 pre-tax benefit?
Log into your Benefits Portal and choose "Home" on the left side menu.
What proof of coverage are you looking for?
Your admin will need to see proof that you enrolled in a 2027 plan. This can be an invoice, receipt, or screenshot of the enrollment page from your health insurance carrier's website.
What do I need to do to keep my current health plan? (I want to renew.)
If you like your plan, you can keep it. Most insurance companies will automatically renew your enrollment for the new year unless you cancel or make changes. A few notes:
- Your 2027 monthly plan price will change. (Prices change every year.)
- Your insurance company should have informed you of your new monthly price. If not, contact them directly.
- You need to set up auto-reimbursements for your 2027 health plan. Your 2026 auto-reimbursements stop in December.
What if I want to change my health plan?
You have until Dec 15 (or your state's deadline) to enroll in coverage that starts Jan 1, 2027. To browse 2027 plans, log into your portal and click Shop.
Can I enroll if I'm getting a premium tax credit?
You can't accept your employer's pre-tax benefit and any federal or state premium tax credit at the same time. You must choose one — either waive your pre-tax benefit or the premium tax credit. If you'd like help deciding which is right for you, email support@stretchdollar.com.
My health plan carrier is leaving the marketplace in 2027. What should I do?
Best to shop for a new plan so you get coverage that fits your needs. Log into your portal and click Shop — you can pick a new plan there or book a meeting with a licensed expert for 1:1 help.
What if I miss the Open Enrollment period?
If you miss Open Enrollment, you can only get coverage if you have a qualifying life event — like getting married, losing other health coverage, or becoming eligible for an ICHRA (like through StretchDollar!). If you've missed the window, reach out to us to understand your options.
How can I get help?
Reach out to support@stretchdollar.com. We have a team of brokers who can meet with you 1:1 to assess your 2027 plan options and make sure you're set up for the new year.