Giftwise

Give to someone on SSI without lowering their check. One PayPal checkout pays the shop, the clinic or their ABLE account directly, routed by Social Security's own rules.

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Giftwise lets a family give to someone on SSI without lowering their check. One PayPal checkout pays the shop, the clinic or the person's ABLE account directly, routed by Social Security's own rules.

Try it in 3 minutes: open Maya's gift page, type $1,500 and pay in the PayPal sandbox (login in the testing instructions, or PayPal's test card 4012 8888 8888 1881). Then open the receipt and press Check with PayPal now.

Inspiration

About 7.4 million people in the US live on SSI, a monthly benefit for people with disabilities and older adults with very little income (CRS IF10482). SSI has a rule most families never hear about: a cash gift counts as income and lowers the check paid two months later (20 CFR 416.1121, POMS SI 00830.520).

Give Maya $1,000 in cash in November and her January check drops from $1,029 to $109. Pay the wheelchair shop directly with the same $1,000 and her check stays $1,029. Same money, same family, $920 apart. Maya is a sample person; the rule is real.

It happens at scale:

Families want to help. The rules make the safe way hard to see. We built Giftwise to make the safe way the easy way to give.

What it does

Giftwise is benefit-safe giving through PayPal, for people on SSI, their families and their benefits counselors. End to end:

  1. Set up a gift page. The organizer lists what the person needs: a wheelchair repair, college books, the electric bill, a therapy co-pay.
  2. Use the person's own numbers. Answer a few plain questions, or upload the letter from Social Security. Claude reads it, code checks every quote word for word against the letter, and the rules work out the check and confirm it matches the letter. Private details are dropped and the file is not kept.
  3. Give any amount. A giver types an amount. A rules engine built from Social Security's regulations and manual splits it across the needs, to the cent, and shows the check before and after.
  4. One PayPal checkout pays everyone. One PayPal order pays each shop and clinic directly, plus the ABLE account's share: up to 10 payees, captured once. Pay with PayPal or a card. Nothing goes to the person's bank or to Giftwise.
  5. A receipt checked with PayPal. Every payee, its PayPal capture ID and the rule that applied. Check with PayPal now asks PayPal for the live status.
  6. A monthly report to share with Social Security. Written from the payments, in full, in Easy Read and in Spanish. A benefits counselor opens it with its code, no login, and PayPal confirms every payment.
  7. Claude reads, code decides. Claude reads letters, bills and fundraiser pages. For a bill that might count as housing, two Claude reviewers read two different rulebooks and must quote them, and code checks every quote. The money is always decided by the rules engine.
  8. Ready for AI agents. An MCP server with nine tools lets an assistant check a gift and start a checkout that only the giver can approve in PayPal.
  9. For organizations. A fund pays many families' needs in one PayPal Payouts batch.

In the sandbox, a PayPal test account stands in for the ABLE account. In production, the ABLE share goes through the ABLE plan's own gift page.

How we built it

PayPal (sandbox)

  • Orders v2 through the PayPal Server SDK: one order with a payee per recipient, built on the server, so money can only reach a payee the rules picked.
  • JavaScript SDK v6 for the PayPal and card buttons, with server-side capture, once, under one PayPal-Request-Id.
  • Payouts, Transaction Search and Balances for organizations, webhooks verified with PayPal, and PayPal's MCP server to read each order back.

AI

  • Claude Opus 5.5 reads letters, bills and fundraiser pages into structured data, runs the two reviewers and explains results in plain words. It never decides the money.
  • Elasticsearch with Jina embeddings powers "Ask the rulebook", answered only from quoted passages.

The rules engine is open source on npm as ssi-gift-rules. Every route cites its section of the regulations or SSA's manual.

Also: Next.js and TypeScript on Render (web, Postgres and nightly Render Workflows checks), AG Studio for the person's year, Bryntum Calendar for the benefit calendar, Channel3 for a benefit-safe gift finder, KERNEL to read fundraiser pages, Postman and Zapier.

Challenges we ran into

  • Rules full of exceptions. Shelter help, loans, rent paid weekly, shared households. We tested the engine on Social Security's own worked examples it had never seen. Each miss pointed to a rule, which we added with its citation.
  • Letting AI help without letting it decide. We measured the AI against no AI. A router with no AI was just as safe; what Claude adds is settling bills straight to the business, so nothing is left for the person to do.
  • Paying many people at once, exactly once. One order, one capture, retried safely with the same PayPal-Request-Id.

Accomplishments that we're proud of

  • Matches 40 of 40 of Social Security's own worked examples.
  • Reaches the same outcome as SSA and the court in 14 of 14 scored federal court cases. In 4 of them, routing the same help through Giftwise would have kept $331 to $663 a month (the engine's estimate at 2026 rates).
  • Lets through 0 of 55 known gifts that would lower the check.
  • With two Claude reviewers, 22 of 28 non-housing bills are paid straight to the business; without AI, 0 of 28.
  • A complete product: gift page, checkout, receipt, report, and setup from the person's own letter.

What we learned

  • PayPal is where the rules are enforced. When the server builds the order, money can only go where the rules allow.
  • Measure AI against no AI before claiming it helps.
  • Two reviewers reading different rulebooks catch mistakes one reviewer misses.

What's next for Giftwise

  • A pilot with one benefits counseling program: 25 families for 120 days, measuring SSI dollars kept.
  • Onboard shops through PayPal Partner Referrals and go live.
  • Hand the ABLE share to each plan's own gift page.

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