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Structured Installment Sale Resource Center
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Chapter 1 · Foundation

History & Origins of the SIS

From thalidomide-era structured settlements to a modern capital-gains tool: the legal and market history of the Structured Installment Sale.

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Content reviewed October 17, 2026 · Educational reference

From structured-settlement roots to a modern installment-sale funding approach.

In plain English

The SIS is the grandchild of the structured settlement. Periodic injury settlements developed to meet long-term needs with scheduled payments rather than a single lump sum. Federal law subsequently established favorable treatment for qualifying injury payments and qualified assignments. The same payment-funding techniques were later adapted for sellers of real estate and businesses. The crucial difference is the tax result: qualifying injury damages can be excluded from income, while an SIS reports otherwise taxable sale gain under the installment rules.

Structured-settlement roots

The structured settlement was born from tragedy. In the 1960s, the morning-sickness drug thalidomide caused severe birth defects in thousands of children. Courts recognized that a single lump-sum award was poorly suited to lifelong needs — lump sums are spent, mismanaged, or lost. Periodic-payment settlements, funded by annuities, emerged as the solution, pushing against the common-law single-recovery rule traceable to Fetter v. Beale (1699).

Federal provisions governing injury settlements help explain the funding architecture, but they do not give a business seller an injury-damages exclusion. The SIS must separately satisfy the installment-sale rules.

  • IRC §104(a)(2) excludes from gross income damages received on account of personal physical injury — including the future investment earnings embedded in periodic payments, provided the claimant never has constructive receipt of the funding asset.
  • Rev. Rul. 79-220 (1979) addressed exclusion of qualifying periodic injury-settlement payments under §104, including amounts exceeding the funding cost. It did not establish that a property seller is taxed only when payments arrive.
  • The Periodic Payment Settlement Act of 1982 (P.L. 97-473), signed by President Reagan, codified the tax treatment and added IRC §130, permitting a qualified assignment that lets a defendant or insurer transfer the periodic-payment obligation to a specialized assignment company.

The industry organized around the qualified-settlement framework, with specialist consultants, assignment companies, insurers, and trade associations such as NSSTA. That history explains the SIS payment-funding model, but settlement-market size and historical premium totals do not measure SIS tax validity, the assets available to a particular seller, or the credit strength of the company that owes that seller.

From settlements to sales: the non-qualified bridge

One obstacle blocked using the qualified-assignment machinery for ordinary asset sales: IRC §130 applies to specified injury or sickness payment liabilities excludable under §104(a)(1) or (2). A real-estate or business sale does not produce those damages. A non-qualified assignment transfers payment duties outside that §130 exclusion. The seller’s gain is governed by §453 and related rules, including payment, disposition, and receipt doctrines. Section 453B(e) addresses a holder’s transfer of an installment receivable to a life insurance company; it is not a blanket prohibition on an insurer assuming a debtor’s duty.

Evolution of the modern SIS

The modern structured sale adapts the established practice of funding future payment obligations through an assignment company and an insurer. Product offerings and the entities underwriting them have changed over time. Demand for alternatives also changed after the Tax Cuts and Jobs Act of 2017 limited §1031 exchanges to real property, leaving sellers of business assets to consider other approaches. Today the advisor must obtain the current product documents rather than infer available terms from the history of structured settlements. MetLife’s current materials, for example, distinguish its traditional SIS from its SIS Flex Agreement; the permitted payment start dates differ (traditional SIS payments must begin within one year; the SIS Flex Agreement permits tailored start dates and lump sums) and the Flex Agreement is a funding agreement, which may not be available in every jurisdiction. Both are issued by Metropolitan Tower Life Insurance Company through MetLife Assignment Company, Inc. An indexed settlement annuity or a product launch in another market does not by itself establish SIS availability.

Historical timeline

1699
Fetter v. Beale
Articulates the common-law single-recovery rule that structured payments would later soften.
1960s
Thalidomide crisis
Mass birth-defect litigation spurs periodic-payment settlements for lifelong care.
1979
Rev. Rul. 79-220
IRS addresses exclusion of qualifying periodic injury payments under §104. IRS holds that qualifying periodic injury payments, including embedded growth, are excludable under §104(a)(2).
1982
Periodic Payment Settlement Act
Codifies tax treatment of structured settlements; enacts IRC §130 qualified assignments.
2005
Allstate Life markets a "structured sale"; Prudential follows
Non-qualified assignment adapted to capital-asset sales — the first modern SIS. The product is described in Wood, "Structured Sales: Breathing Life Into Installment Sales," Tax Notes, July 11, 2005; the Allstate and Prudential attribution is as reported by Finn Financial Group (Wood's article does not name a carrier).
2017
Tax Cuts and Jobs Act
Repeals §1031 for personal property/businesses — catalyzing demand for SIS alternatives.
2018–2019
Independent Life & MetLife enter
Independent Life begins underwriting (2018); MetLife enters the SIS market on a limited-state basis (2018–2019).
Mar 2022
MetLife announces 49-state availability
MetLife's March 9, 2022 release extends its SIS to 49 states (excluding New York); the announcement is sometimes mistaken for its first entry.
2023–2025
Settlement-market records
NSSTA reports record structured-settlement annuity production of $8.623B for 2023 and record levels again in 2025 (dollar figure not published at review); market size does not measure SIS tax validity or any carrier's credit strength.
Jul 2025
New York availability
MetLife's SIS becomes available in New York, completing 50-state availability; the month is per industry reporting (4structures.com, July 8, 2025) — no MetLife release was located, though MetLife's page confirms all 50 states plus Puerto Rico.
2026
Carrier landscape in motion
26North Reinsurance signed a definitive agreement (June 1, 2026) to acquire Independent Insurance Group, parent of Independent Life, pending state regulatory approval; MetLife launched a Non-Qualified Assignment Flex Agreement (June 11, 2026) on the same funding-agreement chassis as its SIS Flex. Reports of additional carriers entering the SIS market should be confirmed against the carrier's own product documents before reliance.

Describe current products by name and date

Product availability and payment options change. A current written proposal should identify the issuer, assignment company, funding instrument, permitted jurisdictions, minimum funding amount, and payment restrictions. The website does not treat a historical carrier list or an undated illustration as a current quote.

For practitioners

Do not import the §104 exclusion or §130 assignment-company tax treatment into an SIS. The relevant inquiry is whether the seller has a qualifying installment obligation and avoids an earlier taxable receipt or disposition. Insurer ownership, seller control, and any guarantee must be analyzed under the actual structure.

Sources: IRC §104 — injury and sickness payments; IRC §130 — qualified assignments; IRC §453 — installment method; Wood, "Structured Sales: Breathing Life Into Installment Sales," Tax Notes (July 11, 2005); MetLife — Structured Installment Sales; MetLife 49-state SIS launch (Business Wire, Mar. 9, 2022); MetLife Non-Qualified Assignment Flex Agreement (Business Wire, June 11, 2026); 26North Re / Independent Insurance Group agreement (Reinsurance News, June 2026; industry reporting). 

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