Related Party Business Transactions
Related-party rules can disallow a loss or postpone a deduction even when the transaction is real. Test the relationship under the applicable provision, then separate loss recognition, payment timing and the later buyer’s sale.
Relationship first, consequence second
| Transaction | Rule to investigate | Wrong shortcut |
|---|---|---|
| Sale at a loss to a related person | Loss disallowance | Deducting the loss because cash changed hands. |
| Accrued expense to a related cash-method payee | Possible deduction deferral until payment/inclusion | Deducting immediately because the payer uses accrual. |
| Buyer later sells the property | Prior disallowed loss may reduce recognized gain | Adding the disallowed loss automatically to basis. |
| Ownership through family or entities | Attribution rules | Looking only at direct ownership percentages. |
Sale at a loss to a related person
- Rule to investigate
- Loss disallowance
- Wrong shortcut
- Deducting the loss because cash changed hands.
Accrued expense to a related cash-method payee
- Rule to investigate
- Possible deduction deferral until payment/inclusion
- Wrong shortcut
- Deducting immediately because the payer uses accrual.
Buyer later sells the property
- Rule to investigate
- Prior disallowed loss may reduce recognized gain
- Wrong shortcut
- Adding the disallowed loss automatically to basis.
Ownership through family or entities
- Rule to investigate
- Attribution rules
- Wrong shortcut
- Looking only at direct ownership percentages.
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For the July 2026-February 2027 SEE window: tax law through December 31, 2025; questions generally use calendar year 2025.
How to work through the decision
- 1Test the relationship
- 2Apply disallowance or deferral
- 3Track later consequences
Disallow the seller’s loss without rewriting the buyer’s cost
When an applicable related-party rule disallows a loss, the seller cannot deduct that loss in the ordinary way. The buyer generally still has cost basis, rather than automatically inheriting the seller’s higher basis. On a later sale by the related buyer, a special recognition rule can reduce the buyer’s gain by the previously disallowed loss to the extent permitted. That is a gain-recognition adjustment, not an unrestricted transfer of the seller’s loss deduction.
If the later gain is smaller than the disallowed loss, the rule can eliminate the gain without creating a new deductible loss for the unused excess. If the buyer later sells below their own cost, the seller’s disallowed loss does not simply enlarge the buyer’s loss. Distinguish realized gain, recognized gain and basis before selecting an answer. Different related-party transfers or property uses can also change gain character.
Original worked example
A related buyer’s later gain
Assume an applicable related-party rule disallows a seller’s $5,000 loss when property with $20,000 basis is sold for $15,000. The buyer later sells to an unrelated person for $18,000; the special subsequent-gain rule applies.
- 1
Buyer’s realized gain = $18,000 - $15,000 = $3,000.
- 2
The eligible prior disallowed loss can offset that gain up to $3,000.
- 3
The unused $2,000 does not turn this transaction into a deductible loss.
Result
Zero recognized gain in this simplified subsequent-sale case.
The buyer’s purchase basis remains $15,000; the offset is a recognition rule.
Apply the method to different facts
Original worked case 2
The later sale exceeds the previously disallowed loss
A parent sells investment property with $30,000 basis to an adult child for $22,000. The $8,000 loss is disallowed. The child later sells to an unrelated buyer for $34,000. Assume the subsequent-gain rule applies and there are no costs or basis changes.
- The child’s purchase basis remains $22,000.
- The child realizes $34,000 - $22,000 = $12,000 gain.
- Reduce recognized gain by the applicable $8,000 previously disallowed loss.
$4,000 recognized gain. If the later price were $26,000, the $4,000 realized gain could be eliminated, but the remaining $4,000 old loss would not become a new deduction.
Mistakes to catch
- Assuming the same relationship definition applies to every code provision.
- Turning an unused disallowed loss into a new deduction for the buyer.
Check your understanding
Does every sale between relatives produce no tax?
No. The specific relationship and transaction matter. A disallowed-loss rule does not generally exempt gains from tax.
2. An accrual company owes deductible interest to a related cash-method payee at year end and pays next year. Is booking the payable enough for the current deduction?
Answer: Generally no under the related-party matching rule.
The deduction is deferred until payment and corresponding inclusion, assuming the rule applies. The accounting entry does not overcome that timing restriction.
3. A related buyer pays $15,000 for property with the seller’s $20,000 basis. Does the disallowed $5,000 loss automatically make the buyer’s basis $20,000?
Answer: No. The buyer generally has $15,000 cost basis.
The possible later-gain offset is separate from basis. Combining them can produce the wrong result when the subsequent sale is at a loss.
Put the rule into practice
Create an account for EA practice, then work on the decisions you missed.
Sources and scope
Source check: . IRS and PSI materials support the factual rules. Worked cases and suggested study sequences are original educational examples, not official exam questions or IRS study requirements.
- PSI SEE Candidate Information Bulletin
Exam format, scored domain allocations, tested tax year and exam procedures; see Study Materials and Examination Content Outlines.
- IRS Publication 544 (2025)
Related-party loss disallowance, subsequent sales and gain character.
- IRS Publication 538
Cash and accrual methods, inventories and accounting method changes. Do not use its older indexed dollar thresholds for 2025.
Use the version applicable to your testing window. Live IRS pages can advance to a later tax year. These notes are exam study material; examples state simplifying assumptions.