Estate planning for Bitcoin often focuses on getting assets out of the taxable estate — into GRATs, FLPs, SLATs, dynasty trusts, and IDGTs. Less attention goes to the provision that can reverse all of that: IRC §2036, the retained interest rule.
§2036 is the IRS's most powerful tool for challenging estate planning transfers. It requires that a decedent's gross estate include any property transferred during life if the decedent retained certain rights over that property. For Bitcoin holders, this has direct implications for every vehicle in the estate planner's toolkit — and Bitcoin's unique characteristics as a bearer asset with on-chain transparency create risks that don't exist for traditional assets.
Understanding §2036 is not optional for serious Bitcoin estate planning. It is the provision your estate planning attorney most needs to design around — and the one the IRS most reliably uses when a large estate is audited. This guide breaks down every subsection, applies each to Bitcoin-specific scenarios, reviews the case law that matters, and provides a concrete compliance checklist.
1. What Is IRC §2036?
IRC §2036(a) states a deceptively simple rule: the gross estate includes the value of all property transferred by the decedent during life if the decedent retained, for any period that does not end before death, one of the following:
- §2036(a)(1): The right to the possession or enjoyment of the property, or the right to the income from the property
- §2036(a)(2): The right, either alone or in conjunction with any person, to designate the persons who shall possess or enjoy the property or its income
Both prongs are deliberately broad. Congress designed §2036 to be the backstop against every form of "gift but keep control" — the pattern where a taxpayer nominally transfers property out of their estate while retaining the economic benefits or decision-making authority that made the property valuable in the first place.
The operative mechanism is straightforward: if §2036 applies, the transferred property is included in the gross estate at its full fair market value on the date of death — not the value at the time of transfer. This distinction is critical for Bitcoin. If you transferred $1 million in Bitcoin to an FLP and Bitcoin appreciated to $10 million by your death, §2036 inclusion brings $10 million into your estate. Every dollar of appreciation that seemed to be outside the estate is recaptured entirely.
The practical effect is devastating. The decedent's estate plan — potentially years or decades of careful structuring — is unwound in a single audit determination. The estate tax is calculated as if the transfer never happened. Worse, the estate may also owe gift tax on the original transfer, creating a double taxation scenario that is among the most punitive outcomes in estate planning.
⚠️ §2036 Is the IRS's Favorite Weapon
§2036 is not a theoretical risk. It is the provision the IRS uses most frequently — and most successfully — in estate tax litigation. The Tax Court has extensive case law interpreting §2036, and the IRS wins more often than it loses. Every Bitcoin estate plan must be designed with §2036 as the primary adversarial constraint, not as an afterthought.
2. §2036(a)(1): Retained Enjoyment
The first prong — §2036(a)(1) — captures retained economic enjoyment. If the transferor kept the right to use, possess, or enjoy the transferred property, or the right to income from it, the property comes back into the estate.
"Enjoyment" is interpreted broadly by courts. It does not require a formal legal right — a de facto pattern of continued use is sufficient. The IRS looks at conduct, not documents. If you transferred Bitcoin to an LLC but continued to use it as if it were personally owned — paying personal expenses from the LLC account, depositing mining income to your personal wallet, or simply retaining possession of the private keys — the IRS will argue that you retained enjoyment under §2036(a)(1).
What Triggers §2036(a)(1) for Bitcoin Holders
- Retained key custody: Transferring Bitcoin to a trust or LLC "on paper" but keeping the hardware wallet or seed phrase that controls the BTC address. The grantor retains physical possession and practical enjoyment of the asset.
- Personal expense payments: Using entity-held Bitcoin (or entity bank accounts funded by Bitcoin sales) to pay the grantor's personal mortgage, credit cards, or living expenses.
- Mining income diversion: Bitcoin mining rewards that should flow to the entity's wallet instead deposited to the grantor's personal address. This is direct income retention.
- Commingled accounts: Entity and personal funds held in the same bank account or cryptocurrency exchange account, making it impossible to distinguish entity property from personal property.
- Informal access: No formal distribution process. The grantor takes Bitcoin from the entity whenever needed, with no documentation, no capital account entries, and no board or manager approval.
The common thread: the transfer looked good on paper but changed nothing in practice. The grantor's relationship to the Bitcoin remained exactly the same before and after the "transfer." Courts see through this pattern every time.
💡 The Substance-Over-Form Doctrine
§2036(a)(1) is fundamentally a substance-over-form provision. The IRS doesn't care what your operating agreement says. It cares what actually happened. If the grantor continued to benefit from the Bitcoin as if no transfer occurred, the documents are irrelevant. The conduct controls.
3. §2036(a)(2): Retained Power to Designate
The second prong — §2036(a)(2) — captures retained decision-making power. If the transferor retained the right, alone or with any other person, to designate who shall possess or enjoy the property or its income, the property is included in the estate.
This is the provision that targets control, not enjoyment. The grantor doesn't have to benefit personally — merely retaining the power to decide who benefits is enough. For Bitcoin FLPs and LLCs, this is where the general partner or manager role becomes dangerous.
The FLP General Partner Problem
Consider the typical Bitcoin FLP structure: the senior family member contributes Bitcoin to the FLP, retains a 1-2% general partner interest, gifts limited partnership interests to children or trusts, and manages the FLP as general partner with authority over investment decisions and distributions.
Under §2036(a)(2), the IRS argues that the general partner's authority to make or withhold distributions constitutes a retained right to designate who enjoys the property. If the general partner can decide when and how much each limited partner receives, the general partner controls who benefits from the FLP's Bitcoin — which is exactly what §2036(a)(2) prohibits.
The risk is heightened when:
- The operating agreement gives the general partner sole discretion over distributions
- Distributions are made selectively — some partners receive distributions while others don't — rather than pro-rata based on ownership
- The general partner retains the unilateral power to dissolve the FLP and return all assets
- The general partner and one family member, acting together, can amend the partnership agreement to change distribution terms
The Tax Court in Estate of Powell v. Commissioner (2017) found §2036(a)(2) inclusion where the decedent and her son, acting together as general partners, could dissolve the FLP and return all assets. The court held that this constituted a retained right to designate who would enjoy the property — even though neither partner could do it unilaterally. The "in conjunction with any person" language in §2036(a)(2) means that joint control counts.
How to Structure the GP Role Safely
- Limit the general partner's distribution authority to pro-rata distributions only — no discretionary or selective distributions
- Require supermajority LP approval for dissolution or material amendments
- Appoint a non-family member as co-general partner or independent manager to dilute the grantor's control
- If the grantor serves as GP, ensure the operating agreement constrains the GP's powers to administrative functions, not distribution discretion
- Consider transitioning the GP role to a younger family member or professional manager within 1-2 years of formation
4. §2036(b): Retained Voting Rights
§2036(b) is a narrower provision that applies specifically to corporate stock. If a decedent transferred shares in a "controlled corporation" but retained voting rights — directly or indirectly — the transferred shares are included in the gross estate.
A "controlled corporation" is one where the decedent held (directly, indirectly, or constructively under §318) at least 20% of the total combined voting power of all classes of stock. The provision was enacted to prevent founders from transferring the economic value of corporate stock to heirs while retaining governance control through voting shares or dual-class structures.
When §2036(b) Matters for Bitcoin
§2036(b) is less relevant for Bitcoin held directly, in trusts, or in LLCs (which don't have "stock" or "voting rights" in the corporate sense). However, it is directly relevant for:
- Bitcoin mining C-corporations: If the founder transfers non-voting preferred stock to heirs but retains common stock with voting control, §2036(b) applies to the transferred shares
- BTC held in corporate treasury: A family-owned corporation that holds significant Bitcoin as a treasury asset, where the founder transfers economic shares but retains voting control
- Dual-class mining company structures: Common in tech companies and increasingly in Bitcoin mining — Class A voting shares retained by founder, Class B economic shares gifted to family trusts
The solution is clean: transfer non-voting shares only (economic interest without voting rights), and ensure the transfer structure does not give the transferor indirect voting control through related parties or contractual arrangements. For Bitcoin mining operations structured as C-corps, this means careful attention to share class design at the entity formation stage — not after transfers have begun.
5. The Bona Fide Sale Exception — The Key Defense
The last sentence of §2036(a) contains the most important exception in estate planning: §2036 does not apply to transfers that constitute "a bona fide sale for an adequate and full consideration in money or money's worth."
This exception is the entire basis for FLP and LLC estate planning. The theory: when a taxpayer contributes Bitcoin to an FLP and receives proportionate partnership interests in return, the transfer is a "sale" (exchange of Bitcoin for LP interests) for "adequate and full consideration" (the LP interests are worth the contributed Bitcoin). If the bona fide sale exception applies, §2036 is irrelevant — even if the taxpayer retains some economic benefit or control as general partner.
What Courts Require for the Bona Fide Sale Exception
Courts have developed a two-part test, derived primarily from Estate of Bongard v. Commissioner (2005):
- Legitimate and significant non-tax purpose: The entity must serve a genuine business purpose beyond estate tax reduction. Investment management, asset protection, family governance, centralized management of a complex Bitcoin position, operational mining activity — these qualify. "We want to reduce estate taxes" does not.
- Transfer for adequate and full consideration: The transferor must receive entity interests that are proportionate to the contributed assets. If you contribute $5 million in Bitcoin and receive 50% of the LP interests in a $10 million FLP, the consideration is adequate. If you contribute $5 million and receive 10% interests, it's not.
The first element — legitimate business purpose — is where most FLPs fail. Courts scrutinize this aggressively. Factors that demonstrate genuine business purpose include:
- Active management: The entity actively manages the Bitcoin position — rebalancing, tax-loss harvesting, DCA strategies, yield generation, staking, or mining operations
- Third-party involvement: Non-family investors, arm's-length management fees, professional custodians, or outside advisors involved in entity operations
- Asset protection: Genuine creditor protection concerns — the entity shields assets from potential litigation, divorcing spouses, or business liabilities
- Operational history: The entity was formed well before any health decline or estate planning urgency, and has a track record of genuine business activity
- Family governance: The entity provides a structured mechanism for teaching the next generation about Bitcoin management, investment discipline, and wealth stewardship
💡 Mining Creates Genuine Business Purpose
Bitcoin mining operations generate real economic activity — equipment procurement, energy contracts, facility management, hash rate optimization, and ongoing operational decisions. An FLP or LLC that includes mining operations has inherent non-tax business purpose that passive Bitcoin holding alone cannot match. This is one reason mining entities are among the most defensible structures for estate planning. The entity isn't just a wrapper around a wallet — it's an operating business.
⛏️ Bitcoin Mining: The Tax Strategy That Also Survives §2036
Mining operations in a properly structured entity create genuine business purpose, real economic substance, and operational activity — the exact attributes that satisfy the bona fide sale exception. Mining income flowing through the entity (not to personal accounts) is a key compliance point for §2036 survival. Explore how mining integrates with entity-based estate planning.
Explore the Mining Tax Strategy →6. What the IRS Looks for in an FLP/LLC §2036 Attack
IRS estate tax examiners are trained to identify §2036 issues in every large estate that includes FLP or LLC interests. The audit playbook is well-established. Here is what triggers a §2036 challenge:
Red Flags That Invite §2036 Litigation
- Commingling of entity and personal funds: Shared bank accounts, entity paying the grantor's personal bills, or personal deposits into entity accounts. This is the single most common §2036 fact the IRS cites.
- No non-tax business purpose: The entity holds only passive investments (including Bitcoin sitting in cold storage) with no active management, no operational activity, and no documented business rationale beyond "estate planning."
- Testamentary nature: The entity was formed during the senior member's final illness, funded with all of their assets, and created primarily to reduce estate taxes. Courts call this a "testamentary substitute" — it functions like a will, not a business.
- Personal use of entity assets: The grantor lives in entity-owned property, drives entity-owned vehicles, or uses entity-held Bitcoin for personal purchases.
- No entity formalities: No annual meetings, no written minutes, no capital account maintenance, no investment policy statement, no formal distribution process.
- Disproportionate distributions: The grantor receives most or all distributions despite owning only a small percentage of interests. This screams "retained enjoyment."
- Deathbed transfers: Assets contributed to the entity within months of the grantor's death, especially if the grantor was in declining health. The timing suggests estate tax motivation, not business purpose.
- No change in management: The grantor continues to manage the Bitcoin exactly as they did before the transfer — same wallet, same exchange accounts, same decision-making authority.
Key Case Law: What the Courts Decided
Estate of Bongard v. Commissioner (2005) — The seminal case establishing the two-part test for the bona fide sale exception. The Tax Court held that the formation of the FLP must be "motivated by a legitimate and significant nontax reason" and that the transfer must be for adequate consideration. Bongard won because the FLP had genuine business purposes (asset protection, centralized management) and was not merely a gifting device.
Estate of Strangi v. Commissioner (2005) — The IRS successfully argued §2036(a)(1) inclusion where the decedent transferred 98% of his assets to an FLP and continued to receive distributions to fund his living expenses. The court found that the decedent retained the practical enjoyment of the FLP assets because his personal lifestyle was entirely funded by entity distributions, and the entity was effectively his personal financial vehicle. The bona fide sale exception failed because there was no legitimate non-tax purpose.
Estate of Powell v. Commissioner (2017) — The Tax Court found §2036(a)(2) inclusion where the decedent and her son, acting together as partners, could dissolve two FLPs and distribute assets. Even though neither could do it alone, the court held that this joint power constituted a retained right to "designate" who would enjoy the property. The decision established that the "in conjunction with any person" language in §2036(a)(2) extends to family members acting in concert.
Estate of Smaldino v. Commissioner (2021, T.C. Memo 2021-127) — The Tax Court found §2036 inclusion where the decedents transferred assets to an LLC and retained the right to enjoy the property through continued personal use and commingled finances. The court emphasized the lack of genuine non-tax business purpose and the testamentary nature of the transfer. However, the court allowed partial bona fide sale treatment for one of the LLCs that had genuine operational activity.
📘 The Pattern That Wins
Across all §2036 case law, the entities that survive IRS challenge share common characteristics: formation well before any health decline, genuine non-tax business purpose documented at formation, strict formalities maintained throughout the entity's life, pro-rata distributions only, no personal use of entity assets, and — critically — a track record of genuine business operations that would justify the entity's existence even without any estate tax benefit.
7. How to Survive a §2036 Challenge for Bitcoin FLPs
Surviving a §2036 challenge is not about having the right documents. It's about having the right conduct — years of operational history that demonstrate the entity is genuine, not a shell. Documents matter, but the Tax Court looks through paper to reality. Here is what reality must look like.
At Formation
- Document the non-tax purpose in writing. The operating agreement, board resolution, or formation memo should state the genuine business reasons for the entity: centralized investment management, asset protection, family governance, operational mining, or multi-party custody coordination.
- Capitalize properly. Each member receives interests proportionate to their contribution. The capital accounts reflect the contributions accurately from day one.
- Appoint independent parties. Include at least one non-family member in a governance role — manager, advisory board member, or co-general partner. This demonstrates arm's-length decision-making.
- Transfer Bitcoin on-chain. The Bitcoin must physically move from the grantor's personal wallet to an entity-controlled wallet on the blockchain. A ledger entry alone is insufficient — on-chain movement is the evidence.
- Establish institutional or multisig custody. The entity's Bitcoin should be held in institutional custody (qualified custodian with the entity as account holder) or in a multisig wallet where the grantor is not the sole signer.
Ongoing Operations
- Annual meetings with written minutes. Document every meeting, every investment decision, every distribution decision. The minutes should reflect genuine deliberation, not rubber-stamping.
- Written Investment Policy Statement (IPS). The entity should have a formal IPS governing its Bitcoin strategy — allocation targets, rebalancing triggers, DCA schedules, risk parameters. This demonstrates professional management.
- Capital account ledger. Maintain accurate capital accounts for all partners/members, updated at least annually. Every contribution, distribution, and allocation of income or loss should be reflected.
- Pro-rata distributions only. All distributions must be proportionate to ownership. If the grantor owns 2% of the entity, the grantor receives 2% of any distribution — not 80% because they "need it for living expenses."
- Separate bank and custody accounts. The entity has its own bank account, its own exchange account, and its own custody arrangement. No commingling with any member's personal accounts.
- Formal distribution process. Distributions require a manager vote or written resolution. No informal withdrawals. No grantor walking to the hardware wallet and sending Bitcoin to their personal address.
- Mining income flows to entity. If the entity operates mining equipment, all mining rewards are deposited to entity-controlled wallets. Mining income that lands in the grantor's personal wallet — even temporarily — is a §2036(a)(1) red flag.
⚠️ Ongoing Compliance Is the Defense
The entities that lose §2036 challenges almost always have clean formation documents. The failure is almost always in conduct — years of sloppy operations that demonstrate the entity was a fiction. The defense is built not at formation but in the years of genuine business activity that follow. If you wouldn't bother to maintain formalities, don't bother forming the entity.
8. GRATs and §2036
A Grantor Retained Annuity Trust (GRAT) occupies a unique position under §2036 — it intentionally creates a retained interest. The grantor transfers Bitcoin to the trust and retains an annuity for a fixed term. The retained annuity is by definition a §2036(a)(1) interest — the right to income from the transferred property.
Congress sanctioned this structure through §2702, which governs how retained interests in family trusts are valued for gift tax purposes. Under §2702, a "qualified interest" (including a fixed annuity) is valued using the §7520 rate, and the gift element equals the transferred value minus the present value of the retained annuity. A properly structured GRAT under §2702 is not "attacked" by §2036 — it is defined by it.
When §2036 Bites: GRAT Death Risk
The §2036 risk materializes if the grantor dies during the annuity term. Under §2036(a)(1), the estate includes the amount of GRAT assets needed to fund the remaining annuity — valued at the date of death using the §7520 rate in effect at death. In practice:
- If Bitcoin appreciated significantly since the GRAT was funded, the estate inclusion can be massive — potentially the entire trust value
- The estate is in roughly the same position as if the GRAT never existed, except it may also owe gift tax on the original transfer
- The appreciation that was supposed to pass tax-free to remainder beneficiaries is recaptured by the estate
Mitigating GRAT §2036 Risk
Short rolling GRATs. Instead of one 10-year GRAT, execute five consecutive 2-year GRATs. At any given time, maximum §2036 exposure is limited to the current term. If the grantor dies, only the current GRAT's remaining annuity obligation is included — not a decade of accumulated appreciation.
Life insurance hedge. An ILIT-held life insurance policy can offset the estate inclusion if the grantor dies during the GRAT term. The policy must be transferred to the ILIT more than three years before death (§2035 three-year rule) to avoid pulling the death benefit back into the estate.
Zeroed-out GRATs. Structuring the GRAT so the gift element is approximately zero (the present value of the annuity equals the value of the transferred Bitcoin) minimizes the gift tax cost if §2036 applies — there was no taxable gift to begin with. The entire planning benefit comes from appreciation above the §7520 hurdle rate.
Improperly Structured GRATs
A GRAT that doesn't meet §2702's qualified interest requirements faces §2036 risk beyond the standard mortality issue. If the annuity payment is not fixed (varies at the grantor's discretion), the retained interest may not qualify under §2702 — and the IRS can argue the entire transfer is a §2036(a)(1) retained enjoyment interest. Ensure the GRAT document specifies a fixed dollar amount or fixed percentage annuity, with no trustee discretion to vary payments.
9. IDGTs and §2036
An installment sale to an Intentionally Defective Grantor Trust (IDGT) is one of the most powerful Bitcoin estate planning techniques. The grantor sells appreciated Bitcoin to the IDGT in exchange for a promissory note bearing the Applicable Federal Rate (AFR). Because the trust is a grantor trust for income tax purposes, the sale is ignored for income tax — no capital gains recognition. But the sale is recognized for estate tax purposes, moving the Bitcoin out of the estate.
How the Bona Fide Sale Exception Protects IDGTs
The IDGT installment sale avoids §2036 through the bona fide sale exception. The grantor sold the Bitcoin — they didn't gift it while retaining enjoyment. The note is the consideration. But the exception only holds if the sale is genuine:
- The note must bear adequate interest. At minimum, the AFR for the note's term. Below-market interest suggests a disguised gift, not a sale.
- Payments must actually be made. The trust must make regular principal and interest payments per the note's terms. Missed payments, forgiven interest, or "flexible" payment schedules undermine the sale's legitimacy.
- The trust must have economic substance. The standard practice is to "seed" the IDGT with assets equal to at least 10% of the purchase price before the sale. This demonstrates the trust has independent economic substance and isn't merely a conduit.
- The grantor cannot retain de facto control. If the grantor is also the trustee of the IDGT with discretionary distribution powers, §2036(a)(2) may apply. Independent trustees are essential.
- The note must be genuine debt. If the note has no realistic prospect of being repaid (the trust has no income and no plan to generate income), the IRS can argue the "sale" is really a transfer with a retained interest in the form of the note.
Bitcoin-Specific IDGT Considerations
Bitcoin's volatility creates both opportunity and risk for IDGT installment sales. If Bitcoin appreciates dramatically after the sale, the trust captures all upside above the AFR — estate planning nirvana. But if Bitcoin declines, the trust may struggle to make note payments, potentially undermining the bona fide sale treatment.
Mitigation: seed the trust with sufficient assets (not just Bitcoin — consider diversified seed capital), structure the note with a balloon payment at maturity rather than high annual payments, and ensure the trust has a clear plan to service the debt through Bitcoin income, sales, or distributions from other trust assets.
10. Bitcoin-Specific §2036 Risks
Bitcoin's characteristics as a bearer digital asset create §2036 risks that don't exist for stocks, bonds, real estate, or traditional assets. Every Bitcoin estate planner must address these:
Risk 1: Retained Key Custody
The problem: The grantor transfers Bitcoin to a trust or FLP but retains sole custody of the private keys — the hardware wallet stays in their safe, the seed phrase remains in their possession. Legally, the Bitcoin was "transferred." Practically, the grantor retains complete, unilateral control.
The §2036 argument: The grantor retained possession and enjoyment (§2036(a)(1)) and the power to designate (§2036(a)(2)) — they can move the Bitcoin to anyone at any time with no other party's consent.
Mitigation: Transfer Bitcoin on-chain to an entity-controlled address. Use institutional custody with the entity as account holder, or multisig where the grantor holds at most one key of a 2-of-3 or 3-of-5 quorum. The grantor alone cannot move the Bitcoin.
Risk 2: Mining Rewards to Personal Accounts
The problem: Mining equipment is nominally owned by the entity, but pool payouts are directed to the grantor's personal wallet address.
The §2036 argument: The grantor retained the right to income from entity property — the textbook definition of §2036(a)(1).
Mitigation: All mining pool payouts must be directed to entity-controlled wallet addresses. Period. No exceptions, no temporary personal custody "for convenience."
Risk 3: Using Trust Bitcoin for Personal Purchases
The problem: The grantor occasionally sells Bitcoin from the trust or entity account to fund personal expenses, vacations, or investments.
The §2036 argument: Retained enjoyment. The grantor is using the transferred property for personal benefit.
Mitigation: All grantor compensation must flow through formal distribution channels — documented, proportionate, and approved by the entity's governance process. No informal withdrawals.
Risk 4: Multisig Where Grantor Is Sole Signer
The problem: The entity uses a multisig wallet, but the grantor holds all keys (e.g., 2-of-3 where the grantor controls all three keys stored in different locations). Technically "multisig" — practically single-signer.
The §2036 argument: Same as retained key custody. The grantor retains complete control. The multisig structure is cosmetic.
Mitigation: At least one key in any multisig quorum must be held by an independent party — a co-trustee, a qualified custodian, or a non-family member with fiduciary obligations. The grantor's keys alone must be insufficient to move funds.
Risk 5: Blockchain Transparency as Evidence
The unique Bitcoin problem: Bitcoin's blockchain is a permanent, public, timestamped ledger. If Bitcoin was supposedly transferred to an FLP but never moved on-chain — remaining at the same address controlled by the grantor's key — there is irrefutable evidence that no genuine transfer occurred. Unlike real estate (where title transfers are recorded but possession is ambiguous), Bitcoin custody is binary and provable.
Mitigation: Every "transfer" to an entity must involve an actual on-chain transaction moving Bitcoin from the grantor's address to an entity-controlled address. The blockchain timestamp, combined with the entity's formation documents, creates an evidence trail that supports genuine transfer of control.
⛏️ Structure Mining Income Correctly From Day One
Mining income flowing to personal wallets instead of entity accounts is the most common §2036 mistake in Bitcoin estate planning. A properly structured mining operation routes all rewards to entity-controlled addresses, creating the clean income trail that survives IRS scrutiny. Our tax strategy resource shows how.
Get the Mining Tax Strategy →11. Recent Case Law: What the Tax Court Focuses On
The Tax Court's §2036 jurisprudence reveals consistent patterns. Understanding what the court prioritizes — and what it dismisses — is essential for structuring Bitcoin transfers that survive.
Estate of Powell v. Commissioner (2017)
Facts: Nancy Powell transferred assets to two FLPs. She and her son served as general partners. The partnership agreements allowed the general partners, acting together, to dissolve the FLPs and distribute assets.
Holding: The Tax Court included the FLP assets in the estate under §2036(a)(2). The joint power to dissolve constituted a retained right to designate who would enjoy the property. The bona fide sale exception failed because the FLPs lacked sufficient non-tax business purpose.
Lesson for Bitcoin holders: Even shared control is dangerous. If the grantor and any other person — especially a family member — can act together to unwind the entity, §2036(a)(2) applies. The operating agreement must prevent this by requiring supermajority votes (including non-family members) for dissolution.
Estate of Smaldino v. Commissioner (2021)
Facts: The Smaldinos transferred assets to multiple LLCs. They continued to use LLC-held property for personal purposes, commingled personal and entity funds, and treated the LLCs as personal accounts.
Holding: §2036(a)(1) inclusion for the LLCs where personal use and commingling were prevalent. However, the court allowed partial bona fide sale treatment for one LLC that had genuine operational activity and maintained better formalities.
Lesson for Bitcoin holders: The court distinguishes between entities with genuine operations and those that are merely wrappers. A Bitcoin LLC that actively manages investments, conducts mining, or engages in real business activity has a materially better chance of surviving §2036 than one that simply holds BTC in cold storage.
What Wins vs. What Gets Clawed Back
| Factor | Wins (§2036 Defeated) | Loses (Estate Inclusion) |
|---|---|---|
| Business purpose | Documented at formation, genuine operational activity | "Estate planning" as sole stated purpose |
| Timing | Entity formed years before death, during good health | Deathbed formation, funded during final illness |
| Formalities | Annual meetings, minutes, capital accounts, IPS | No records, no meetings, no formal processes |
| Distributions | Pro-rata only, formally approved | Selective, informal, grantor receives disproportionate share |
| Custody/control | Institutional custody, multisig, independent parties | Grantor holds all keys, sole signer, self-custody |
| Accounts | Separate entity accounts, no commingling | Shared accounts, personal expenses from entity |
| Third parties | Non-family manager, outside advisor, professional custodian | Family-only control, no outside involvement |
12. The §2036 Compliance Checklist: 15 Items for Bitcoin Entities
Surviving a §2036 challenge requires ongoing discipline, not just good formation documents. Use this checklist as your annual compliance audit for any entity that holds Bitcoin transferred from a senior family member.
Annual §2036 Compliance Checklist
- Separate bank accounts: Entity has its own bank account(s) with no personal funds commingled. Verify no personal deposits or withdrawals occurred this year.
- Separate custody accounts: Entity Bitcoin is held in institutional custody or multisig wallet in the entity's name — not the grantor's personal hardware wallet or exchange account.
- Formal distributions only: All distributions this year were approved by written resolution or manager vote. No informal withdrawals by any member.
- Pro-rata distributions: All distributions were proportionate to ownership percentages. No member received a disproportionate share.
- Investment Policy Statement (IPS) in writing: The entity has a current, written IPS governing its Bitcoin and other investment strategy. The IPS was reviewed and updated this year.
- Annual meeting held and documented: The entity held at least one formal meeting this year with written minutes documenting decisions, investment review, and any distributions.
- Non-tax business purpose documented: The entity's non-tax business purposes are documented in the operating agreement, meeting minutes, or a separate purpose statement reviewed annually.
- Mining income directed to entity: If the entity operates mining equipment, all pool payouts were directed to entity-controlled wallet addresses. No mining income was routed to any member's personal wallet.
- Capital account ledger updated: Capital accounts for all members/partners are current, reflecting this year's contributions, distributions, and allocations of income or loss.
- No personal use of entity assets: No member used entity-held Bitcoin, entity bank accounts, or entity property for personal purposes this year.
- Multisig quorum includes non-family signer: If the entity uses multisig custody, at least one key in the signing quorum is held by a non-family member (independent trustee, qualified custodian, or professional fiduciary).
- On-chain transfers documented: Any Bitcoin contributed to the entity this year was transferred via on-chain transaction from the contributor's personal address to the entity's address. Transaction IDs are recorded.
- GP/Manager powers limited: The general partner or manager's powers are limited to administrative functions. Distribution authority is constrained to pro-rata amounts or requires LP/member approval.
- Dissolution requires supermajority: The operating agreement requires supermajority vote (including non-family members) for dissolution. No single member or pair of family members can unwind the entity unilaterally.
- K-1s and tax returns filed: The entity filed its partnership or LLC tax return (Form 1065) and issued K-1s to all members. Tax compliance demonstrates the entity is treated as a genuine separate entity.
Any item that fails this checklist is a §2036 vulnerability. Address it immediately — before the next audit cycle, not after.
13. §2036 and Bitcoin SLATs
A Spousal Lifetime Access Trust (SLAT) transfers Bitcoin to an irrevocable trust for the benefit of the grantor's spouse. By design, the grantor retains no direct interest — addressing §2036 at the structural level. However, §2036 risk surfaces through two mechanisms:
The Reciprocal Trust Doctrine
If both spouses simultaneously create SLATs for each other — Spouse A creates a SLAT for Spouse B's benefit, and Spouse B creates a SLAT for Spouse A's benefit — the IRS (applying United States v. Grace, 1969) may "uncross" the trusts. The result: each grantor is treated as having created a trust for their own benefit. §2036(a)(1) applies — each grantor retained the right to income from their own trust's assets — and both trusts are pulled back into their respective estates.
To avoid the reciprocal trust doctrine: stagger SLAT creation by at least 6–12 months; use different trust terms, distribution standards, and beneficiary classes; use different trustees and investment advisors; fund with different assets and at different Bitcoin cost bases.
Indirect Economic Benefit
If SLAT distributions to the grantor's spouse free up marital income that would otherwise be spent on joint expenses, courts may find that the grantor is indirectly enjoying the trust's assets. This risk is higher in community property states and where the SLAT effectively replaces the grantor's obligation to support the household.
14. §2036 and Retained Control in Bitcoin Directed Trusts
§2036(a)(2) — the right to designate who receives the property — captures retained decision-making power. For Bitcoin trusts where the grantor serves as trustee with broad discretionary powers, this is a live risk.
The solution: use an independent trustee for any trust intended to be outside the grantor's estate. If the grantor wants investment control, a directed trust structure — grantor as investment director, independent trustee for distributions — is available in most states and doesn't create §2036(a)(2) issues because the grantor controls what the trust invests in, not who benefits.
| Structure | §2036(a)(1) Risk | §2036(a)(2) Risk | Primary Defense |
|---|---|---|---|
| GRAT (grantor survives term) | Resolved — no retained interest at death | No retained designation power | Survive the annuity term |
| GRAT (grantor dies during term) | Inclusion of remaining annuity value | No §2036(a)(2) issue | Short terms + life insurance hedge |
| FLP (bona fide sale) | Exception applies | GP role scrutinized | Business purpose + formalities |
| FLP (no business purpose) | Full inclusion | GP control = §2036(a)(2) | None — restructure required |
| IDGT installment sale | Swap power = grantor trust; not §2036 | No retained designation | Genuine note + independent trustee |
| SLAT (non-reciprocal) | No retained economic benefit | Independent trustee | Staggered creation, different terms |
| SLAT (reciprocal) | Doctrine uncrosses both trusts | Both estates may include trust assets | Avoid mirror structures |
| Directed trust (grantor as investment director) | Investment control ≠ enjoyment | Distribution trustee is independent | Bifurcated control structure |
| Dynasty trust (grantor as trustee) | Depends on trustee powers | Discretionary powers → §2036(a)(2) | Independent trustee required |
15. §2035: The Three-Year Rule Companion
§2035 works alongside §2036 in one critical context: if the decedent relinquished a §2036 retained interest within three years of death, §2035 pulls the property back into the estate anyway. This prevents deathbed fixes — a grantor who realizes their FLP has §2036 problems cannot simply resign as general partner on their deathbed and claim the retained interest ended before death.
For Bitcoin holders using an ILIT to hedge GRAT mortality risk, §2035's three-year rule also applies to life insurance transfers: the policy must be transferred to the ILIT more than three years before death to stay outside the estate. Establish the ILIT early — before the GRAT — to run the clock.
Frequently Asked Questions
What is IRC §2036 and why does it matter for Bitcoin estate planning?
§2036 requires a decedent's gross estate to include any property transferred during life if the decedent retained the right to possession, enjoyment, or income from the property — or the right to designate who receives it. For Bitcoin holders who transferred BTC to trusts, FLPs, or LLCs, §2036 can pull the full date-of-death value back into the taxable estate if the transferor retained any form of control. Because Bitcoin can appreciate dramatically, §2036 inclusion can mean millions in unexpected estate taxes. It is the single most important provision to design around in Bitcoin estate planning.
What is the bona fide sale exception under §2036?
Transfers made for adequate and full consideration in a genuine arm's-length transaction are excluded from §2036. For Bitcoin FLPs and LLCs, this means the transfer must serve a legitimate non-tax business purpose, the transferor must receive proportionate entity interests, and the entity must operate with genuine formalities. The bona fide sale exception is the primary defense in FLP and LLC estate planning — but courts apply it rigorously, and conduct matters more than documents.
Can I keep my hardware wallet keys after transferring Bitcoin to a trust or FLP?
No. Retaining sole custody of private keys after transferring Bitcoin to an entity is the single most dangerous §2036 fact pattern. The IRS will argue — with strong evidentiary support from the blockchain — that you retained possession and enjoyment. Genuine transfers require institutional custody in the entity's name or multisig where the grantor is not the sole signer. The Bitcoin must actually move on-chain to an entity-controlled address.
What happens to a GRAT if the grantor dies during the annuity term?
Under §2036(a)(1), a portion of the GRAT assets — the amount needed to fund the remaining annuity at the §7520 rate — is included in the estate. If Bitcoin appreciated significantly, this can approach the full trust value. Short rolling GRAT terms (2-3 years) minimize the mortality window. Life insurance in an ILIT can offset the inclusion. GRATs are explicitly designed around §2036 — the risk is known and manageable, not hidden.
What did Estate of Powell teach us about §2036 and FLPs?
In Estate of Powell v. Commissioner (2017), the Tax Court included FLP assets in the estate under §2036(a)(2) because the decedent and her son, acting together, could dissolve the FLP. The critical lesson: even joint control with family members triggers §2036. The "in conjunction with any person" language means shared power to unwind an entity is as dangerous as sole power. Operating agreements must require supermajority votes including non-family members for dissolution.
How do IDGTs avoid §2036 challenges?
IDGT installment sales rely on the bona fide sale exception — the grantor sold assets for a genuine promissory note, not a gift with retained enjoyment. The note must be genuine (AFR interest, regular payments actually made), the trust must have economic substance (10% seed capital), and the grantor cannot retain de facto control. An independent trustee is essential. When properly structured, the IRS has little basis for a §2036 argument because the transfer is a sale, not a gift.
Does §2036 apply to SLATs?
Generally no — the grantor retains no direct interest. The risk arises through the reciprocal trust doctrine: mirror SLATs created simultaneously for each spouse may be "uncrossed" by courts, treating each grantor as having retained their own trust's benefits. Stagger creation by 6-12 months with different terms, trustees, and funding assets to eliminate this risk entirely.
What is the most important thing I can do to protect my Bitcoin FLP from §2036?
Maintain ongoing operational discipline. Formation documents are necessary but insufficient. What the Tax Court actually examines is conduct — years of genuine business activity, strict formalities, separate accounts, pro-rata distributions, written minutes, and actual transfer of Bitcoin custody to entity-controlled addresses. The entities that survive §2036 challenges are the ones that operated as genuine businesses every single year, not just on the day they were formed.
Bitcoin Estate Planning Strategy — Waitlist
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This article is for informational purposes only and does not constitute legal, tax, or financial advice. §2036 analysis is highly fact-specific and depends on the structure of each trust or entity, state law, and the decedent's conduct during life. Tax law may change — consult qualified estate planning attorneys and CPAs for your specific situation.
Related Reading
- The Complete Bitcoin Estate Planning Guide
- Bitcoin Family Limited Partnerships: Valuation Discounts and §2036 Survival
- Bitcoin Valuation Discounts in Estate Planning
- Bitcoin GRATs: Transfer Appreciation Tax-Free
- Bitcoin Directed Trusts: Bifurcated Control Structures
- Installment Sales to IDGTs: Shift Appreciation Out of Your Estate
- Bitcoin SLATs: Spousal Lifetime Access Trusts
- Bitcoin Dynasty Trusts: Multigenerational Wealth Transfer
- Bitcoin ILITs: Irrevocable Life Insurance Trusts
- Bitcoin Estate Planning Clawback Protection