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How do I enroll in my health benefits?

New to OS BENEFiTS? Here's how to log in, complete your onboarding, and activate your health coverage — step by step. Takes just a few minutes to get set up.

Updated this week

Enrolling in your health benefits through OS BENEFiTS is easier than you think — and we're with you every step of the way. Here's exactly what to expect.

Step 1: Log in to your OSB Dashboard

Head to your OSB Dashboard and enter your email address. You'll receive an email from OS BENEFiTS with the subject line "Your Magic Login Link" — open it and click the yellow "Login to Dashboard" button to access your account.

Keep an eye out for it in your inbox — the link expires, so use it as soon as it arrives. If you don't see it, check your spam or junk folder.

Step 2: Open your enrollment

Navigate to the Health Care Plan section of your dashboard. You'll see an Open Enrollment card — click it to start. Your progress saves automatically as you go, so you can take your time and come back whenever you need to.

Step 3: Verify your personal information

The first screen is "About You." Review and confirm your personal details — name, date of birth, address, gender, sex assigned at birth, and Social Security Number. Your SSN is fully encrypted and only used to verify your enrollment. Make sure everything looks right before moving on.

Step 4: Add dependents (optional)

Next you'll see "Add Dependents." If you want to add a spouse or children to your coverage, click Add New Dependent and enter their full name, date of birth, Social Security Number, and gender. You can edit or remove dependents anytime before you finalize. If you're not adding anyone, you can skip ahead.

Step 5: Select your health insurance plan

On the "Select Your Health Insurance Plan" screen, you'll see the plans your employer has made available. A few tips from this screen:

  • Use the Compare checkbox to view up to three plans side by side

  • If you added dependents, your coverage tier and monthly cost update automatically so you can see the full picture

  • The price shown is your cost after your employer's contribution

  • Click View Plan Details to download the full summary of coverage for any plan

Select the plan that works best for you and move to the next step.

Step 6: Select voluntary benefits (optional)

Next up is "Voluntary Benefits." Depending on what your employer has chosen to offer, you may see options to add Comprehensive Dental and/or Essential Vision coverage here. Both are completely optional — enroll in what makes sense for you, or skip for now. Your monthly premium will be shown on each card before you select.

Step 7: Review and confirm

The final screen shows your full enrollment summary — all selected plans, who's covered, monthly costs, and your coverage effective date. Review everything carefully, then confirm your enrollment.

Step 8: You're done!

Once submitted, you'll see a confirmation screen showing your enrollment is complete. You'll also be able to view your selections and coverage effective date from your dashboard at any time.

Still need help getting started? We've got you covered. Reach out to Pearl:

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