The Knowledgebase

The Structured Installment Sale, in full.

Ten core chapters, fifteen Deep Dives, forty FAQs, an eight-part authority catalog, and a shared glossary — carrier-neutral, cited to primary sources, and written at two reading levels.

Results open the exact section. Matches found only in practitioner detail are labeled.

10 core chapters15 deep dives40 FAQs8 authority parts79 glossary termsReviewed September 13, 2026

Core Chapters10chapters

Core Chapters

The reading path. History, mechanics, tax framework, substitution, use cases, comparisons, regulation, safety, trade-offs, and implementation.

Browse the chapters →Deep Dives15articles

Deep Dives

The question-driven layer. Allocation and character, parties and entities, timing and cost of tax, protection and geography.

Browse the Deep Dives →Questions40answers

Frequently Asked Questions

Short, sourced answers to the questions sellers and advisors ask first — each one linked to the chapter that goes deeper.

Browse the questions →Authorities & Reference8parts · 79 terms

Authorities & Reference

Code, regulations, rulings, cases, and publications with what each says and how it applies; plus the glossary, sources, and review log.

Open the authority catalog →

Frequently asked questions

Start with a question.

Forty answers, reviewed with the chapters. Each one links to the section that carries the full analysis.

All 40 questions →

Getting startedWhat exactly is a Structured Installment Sale?Read the answer →Getting startedIs the buyer completely released after funding?Read the answer →Tax questionsHow is each payment taxed?Read the answer →Payments & protectionWhat happens if the insurer or assignment company fails?Read the answer →Payments & protectionCan remaining payments pass to my heirs, and are they tax-free?Read the answer →Other approachesIs an SIS the same as a Deferred Sales Trust?Read the answer →

Start here

Two ways in.

Pick the path that matches who you are. Every page carries a Plain English / Practitioner toggle, so either path can go as deep as you need.

I'm selling an asset.

The story, the mechanics, and an honest look at the trade-offs — before the numbers.

I'm advising a seller.

The installment-method rules, the substitution question, and the authorities behind each position.

Core chapters

Ten chapters, in reading order.

All chapters →

Foundation

History & Origins of the SIS How an SIS Works The Tax Framework: IRC §453 in Depth

The Structure

The Substitute-Obligor Question Use Cases by Asset Type SIS vs. Other Deferral Strategies

Regulation & Safety

Regulatory Framework Safety & Security of the SIS

Evaluation & Implementation

Pros, Cons & Risk Analysis Implementation Checklist / Setup Guide

Deep Dives

Go deeper on one issue.

All 15 →

AllocationThe Goodwill-Designation QuestionCan the note be tied to goodwill rather than spread pro-rata across every asset?TimingLarge Sales: §453A Interest & the Pledge RuleThe interest charge and the borrowing rule are separate tests.PartiesWho Is the Seller, Taxpayer & Payee?The name on the check does not decide who sold the asset or owes the tax.TimingOriginal Issue Discount (OID) in a Structured Installment SaleEvery §453 note is a debt instrument, whether or not the documents say so.ProtectionPayment Protection: From Contract to InsolvencyA brand, a rating, and a coverage table answer different questions.

Reference

The shelf behind the chapters.

AuthoritiesRegulatory AuthoritiesEight parts, from the Code to the master authority maps.Glossary79 termsShared with the tooltips and the FAQ. Each term links to its topic.DevelopmentsCurrent DevelopmentsReview log, source status, and the maintenance process.SourcesSources & ReferencesPrimary authorities, IRS publications, and commentary cited.QuestionsFAQ40 expanded answers, each linked to its chapter.

Prefer one continuous page? Read all 37 sections in a single scroll.

See the numbers for your own sale.

The SIS Analyzer compares strategies side by side using the same rules these chapters explain.

Open the SIS Analyzer →