Work more. Worry less about your benefits.
Work Worry-Free checks every paycheck against Social Security's rules, warns you before a month could cost you, reminds you to report, and builds a proof packet you can send if Social Security ever says you owe money back.
Example screen
Working on benefits shouldn't feel like a trap.
The rules are real, but so are the mistakes. Most overpayments happen because a change wasn't reported on time.
of people who started SSDI in 2008 and whose work put them at risk were overpaid within 10 years. The median overpayment was $9,206.
Social Security Bulletin, Vol. 84 No. 1, February 2024of SSI overpayments, and 72% of Social Security (SSDI and retirement) overpayments, were linked to information that wasn't reported on time.
SSA Office of the Inspector General, February 2025trial months are all SSDI gives you before earnings above the limit can stop your check. Knowing where you stand matters.
20 CFR 404.1592Three steps, a few minutes a month.
Add each paycheck
Snap a photo of your pay stub or type in two numbers: the pay date and the pay before taxes. Keep the photo as proof, or let it be deleted once it's read. Your choice.
See where you stand
Trial months used, the SSDI earnings limit, your estimated SSI check, and what's coming up next, in plain English with the official source one tap away.
Report and keep proof
A reminder before the 6th, exactly what to say, and a safe place for your confirmation number. If Social Security ever asks, your proof is ready.
If Social Security says you were overpaid, send them your proof in one tap.
Overpayment letters often come years later, when the pay stubs are long gone. Work Worry-Free keeps everything as you go, then puts it in one clean PDF you can email, print or bring to your local office.
- Every paycheck, by month, the way SSDI and SSI each count it
- Photos of your pay stubs, so you have evidence even if the paper is gone
- Every report you made, with confirmation numbers and what you reported
- Letters and deadlines, plus how each month counted under the rules
- A record history showing when each entry was made or changed, checked against an add-only server copy
Send it with an appeal (form SSA-561) or a waiver request (form SSA-632), or share it with a benefits counselor. It's your record, made from what you entered. Social Security makes the final decision.
Example pages
Built for every kind of body and brain.
When you set it up, the app asks what would make things easier, not what your diagnosis is. Then every screen adjusts.
Big, clear text
Large text and extra-large buttons, with a typeface designed for low vision.
Read aloud
Every page can read itself to you, and buttons are labeled for VoiceOver and TalkBack.
Colorblind and high contrast
Colors you can tell apart, and statuses that never rely on color alone.
Calm wording
Gentle, clear messages for anxiety. No scary red alerts, no surprises.
Simple mode
Fewer choices on each screen for brain fog or memory trouble.
Fewer steps
Snap a pay stub instead of typing, for low energy and pain days.
Large-print summary
One page that says where you stand, in big type, to print or show a caseworker.
Helpers welcome
Parents, payees and job coaches can track someone they help, or share from their own phone.
Try it right here: tap Display at the top of this page for dark mode, colorblind colors, high contrast and larger text. Read our accessibility statement.
Everything that usually lives in a shoebox and a worried head.
Trial months, counted for you
SSDI's 9 trial months in the rolling 60-month window, the earnings limit, grace months, and the 36-month safety net after it.
SSI check estimates
About how much your SSI check will be two months ahead, with a heads-up before months with 3 paydays.
Warnings before trouble
Know before a month uses a trial month, goes over the limit, or pushes your savings over SSI's $2,000 limit on the 1st.
Scan pay stubs
Take a photo and the numbers fill in. If a stub shows your full Social Security number, its photo stays on your phone.
Help with letters
What a Social Security letter means in plain words, your choices, and the deadlines, added to your calendar in one tap.
Reminders that respect you
A monthly nudge to report, on the day and time you pick. Never shows your pay on the lock screen.
Records you can trust
Every change is written down with the date. If you report a month and change it later, the app tells you.
Sources on every result
Each answer links to the Social Security page or rule behind it, so you or your counselor can check it.
Private by default
No Social Security number, no ads, nothing sold. Face ID lock, and cloud backup only if you turn it on.
Start free. New subscribers can try any plan free for 14 days.
Prices in U.S. dollars; your app store shows the price in your currency before you confirm. Plans renew automatically until you cancel in your App Store or Google Play settings, and we remind you 2 days before a free trial ends.
Free
- Check any month's pay
- How to report, with a phone script
- Letter explainer with dates
- A monthly reminder to report
Essentials
or $34.99 a year
- Everything for people who get SSI only
- SSI check estimates and 3-payday warnings
- $2,000 savings check
- Proof of every report
- Proof packet PDF
- Cloud backup
Plus
or $48.99 a year
- Everything in Essentials, plus SSDI
- Trial months, earnings limit and grace months
- Cloud backup
- Proof packet PDF
Family
or $78.99 a year
- Everything in Plus
- Up to 3 people, like yourself and someone you help
- Share with a helper's phone
Coming soon Auto paychecks add-on for any paid plan (not available yet, no date set, price may change): your pay comes in straight from your employer's payroll, $2.99 a month per person.
Good questions, straight answers.
Is this from Social Security?
No. Work Worry-Free is an independent app. It is not part of, or approved by, the Social Security Administration. It uses Social Security's published rules and amounts, and tells you where each number comes from. You still report to Social Security yourself, and the app shows you how.
Do I need to give my Social Security number?
No. The app never asks for it. It only needs your pay amounts and dates, and a few questions about your benefits.
Does it report my pay to Social Security for me?
Not yet. It tells you what to report, when, and how (online, with Social Security's wage reporting app, or by phone), and saves your proof afterward. If Social Security has told you it gets your pay from your employer through its Payroll Information Exchange (PIE), tell the app and it turns your monthly report into a quick check instead.
How accurate is it?
The math is plain, tested code built from Social Security's published rules, checked by more than 130 automated tests of the benefit rules. No AI makes benefit decisions. Some situations are complex (like subsidies or averaging uneven pay), and the app says so. Social Security always makes the final decision, and a free benefits counselor can review your situation: 1-866-968-7842.
Is my information private?
Your records stay on your phone unless you turn on cloud backup. If you scan a pay stub, it's sent securely to our server and an AI service to read the numbers; the AI service may keep it briefly for safety checks. You choose whether to keep the photo as proof. If it shows your full Social Security number, it never goes to cloud backup. We don't sell your information, and there are no ads. See our privacy policy.
Is the app accessible?
It was designed for accessibility from the start: large text, screen reader labels and read-aloud on every page, colorblind and high-contrast modes, calm wording, a simple mode and fewer steps. Tell us anything that gets in your way at hello@workworryfree.com.
Can I get the proof packet for free?
The proof packet comes with every paid plan, and new subscribers can try any plan free for 14 days. The free version still explains letters and shows you how to report.
I help someone else. Can I use it for them?
Yes. Choose "someone I help" during setup. The Family plan covers up to 3 people, and you can share access with another helper's phone.
When can I get the app?
Work Worry-Free is coming to iPhone and Android. The free calculator works right here in your browser now.
Who makes Work Worry-Free?
Work Worry-Free is made by Blue Ridge Labs LLC, a small company in Tennessee. We're independent, and we're not part of the government. Reach us anytime at hello@workworryfree.com.
Know where you stand before you pick up the next shift.
Try the free calculator now. The app is coming soon to iPhone and Android.