Social Security & Investment Income Tax Tool

Upload a Form 1040 — see whether interest or dividend income is causing Social Security taxation or a Medicare IRMAA surcharge, and estimate a strategy to reduce it.

🔒 Your data: uploaded tax returns are deleted immediately after analysis. Generated PDF reports are automatically deleted after 30 minutes. Privacy Policy
or drag and drop file(s) here
Scanned or digital, up to 40 MB total. Multiple pages? Select several files at once, drag-and-drop them together, or tap "Scan with camera" once per page to add them in order. Nothing is stored beyond generating your report — uploaded files are deleted immediately after analysis, and the generated PDF is deleted after 30 minutes.
Filing status, tax year, age 65+/blind boxes, and OBBBA senior deduction eligibility are all auto-detected from the document and can be reviewed and corrected on the results page after analysis — no need to set them here.
Ages (optional)
Optional — flags when someone is about to turn 65 (extra standard deduction, Medicare eligibility) in the report below. Leave the spouse field blank if not filing jointly. Both can still be set or corrected on the results page.
Medicare / IRMAA
Leave blank to use the CMS national benchmark estimate instead.
Strategy illustration (optional)
The specifics (is the income being spent on living expenses, principal amount, rate overrides, etc.) are asked on the results page after analysis, where they can be adjusted and recalculated as many times as needed.
Other options
Capital gains are taxed at ordinary rates in the dollar-impact estimate — exact for short-term gains, but likely overstates the direct tax on long-term gains (which get preferential federal rates).
or
No document to scan? Skip straight to a blank Return Summary and type the figures in yourself — anything already filled in above (ages, Medicare details, strategy exploration) carries over.
What does this tool actually do?

It OCRs a Form 1040 (and works with digital PDFs too), pulls Social Security benefits, interest, and dividend income, then runs the real IRS Social Security Benefits Worksheet twice — once as filed, once with the interest/dividend income removed — to isolate exactly how much of the SS-benefit taxation (and, separately, any Medicare IRMAA surcharge) is attributable to that income.

Optionally, it illustrates a Tax-Deferred Annuity or Split Annuity strategy to reduce or eliminate that impact, using real, periodically-refreshed carrier rate data where available, and estimates any resulting Roth conversion room.

Every figure is computed from public IRS/CMS data and disclosed assumptions — nothing here is personalized advice.