benchmark stringclasses 2
values | id stringlengths 14 31 | instructions stringclasses 1
value | jurisdiction stringclasses 12
values | persona unknown | prompt stringlengths 84 1.23k | scores dict |
|---|---|---|---|---|---|---|
adversarial | hard_tax_questions_90_CA1 | null | California | null | A California founder exercises/sells NQOs at a **~52.65% blended fed+CA marginal rate** and separately expects a large federal §1202 QSBS exclusion. **Does California conform to §1202, at what top marginal rate does CA tax the *non-excluded* gain (noting CA has no LTCG preference), and how is the 1% Mental Health Servi... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_CA10 | null | California | null | A CA taxpayer recognizes a **$3.4M** one-time gain pushing taxable income far above $1M. **How does the §17043 1% Mental Health Services Tax apply only to the increment over $1M, how does it stack with the 12.3% top bracket for a 13.3% effective top, and does it apply to capital gains identically to ordinary income (no... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_CA11 | null | California | null | A CA-nexused corporation in a multinational group considers a **water's-edge election**. **What does the §25110 water's-edge election exclude from the combined report, what is the 84-month binding period, and how does the election interact with the throwback/throwout sourcing of sales for the single sales-factor apport... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_CA2 | null | California | null | A taxpayer moves from CA to a no-tax state mid-year and later sells stock/options that vested while a CA resident. **Under R&TC §17952 and the FTB's sourcing rules, how much of the option/RSU gain remains CA-source after departure, how is the "allocation ratio" for equity comp computed by workdays, and does a change of... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_CA3 | null | California | null | A California LLC has **$2.4M** of total California gross receipts. **What is the §17942 LLC gross-receipts fee at that level, is it in addition to the $800 minimum franchise tax, is the fee based on gross receipts (not net income), and how is it estimated/paid (Form 3536) with what underpayment penalty exposure?** | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_CA4 | null | California | null | An out-of-state investor holds a **15% interest** in a California LLC but has no physical presence in CA. **Under R&TC §23101(b) bright-line factors (sales/property/payroll thresholds) and the *Swart* decision, does the passive member have CA "doing business" nexus and a $800 filing obligation, and how does the FTB's *... | {
"base_model": {
"accuracy": {
"mean_score": 4,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_CA5 | null | California | null | A CA pass-through elects the PTE tax; the owner has both the PTE credit and other nonrefundable credits. **How is the 9.3% PTE elective tax computed on qualified net income, in what §17039 ORDER is the PTE credit applied relative to the OSTC (other-state tax credit), and why can improper ordering cause a permanent loss... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_CA6 | null | California | null | A CA partnership allocates income to a nonresident partner. **What is the §18662 withholding rate on CA-source distributive share, when is Form 592/592-PTE required, how does a nonresident's Form 588 waiver work, and how does this interact with the PTE elective tax already paid?** | {
"base_model": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 4.5,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_CA7 | null | California | null | A married CA couple holds appreciated stock as community property; one spouse dies. **How does §1014(b)(6) give a FULL (double) basis step-up on BOTH halves of CA community property, how must title/agreement establish community-property character, and how does this differ from a common-law state's half step-up?** | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_CA8 | null | California | null | An investor rolls a capital gain into a **Qualified Opportunity Fund** for federal deferral. **Does California conform to the §1400Z-2 QOZ gain deferral/exclusion, how must the investor add back the deferred gain on the CA return, and what is the CA basis-tracking divergence when the QOF is eventually sold?** | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_CA9 | null | California | null | A CA resident maxes an HSA. **Why does California NOT conform to the federal HSA deduction (contributions are CA-taxable and account earnings are CA-taxable annually), how are the CA additions computed on Schedule CA (540), and what basis records must be kept for the eventual distribution?** | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F1 | null | Federal | null | A taxpayer sold operating business assets in 2025 to a related S-corporation on a **4-year installment note (2025–2028)** and recognizes **$32,500** of long-term §1231 installment gain in 2026 (year 2). MAGI is well above the NIIT threshold and there is large passive interest/dividend income. **Is the $32,500 §1231 ins... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F10 | null | Federal | null | A partner dies owning a 25% interest with **$900k** of inside/outside basis disparity; the partnership has no §754 election in place. **Can the estate force a §754 election, how is the §743(b) adjustment computed and allocated among partnership assets under §755, and what happens to the adjustment if a §708 termination... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 7,
"n_runs": 1
}
},
"harne... |
adversarial | hard_tax_questions_90_F11 | null | Federal | null | A partnership has **$2.4M** business interest expense and is subject to §163(j). **How is the 30%-of-ATI limit applied at the partnership level, how does excess business interest expense (EBIE) get allocated to partners and suspended, and what event at the partner level frees up the EBIE — and how does that interact wi... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_F12 | null | Federal | null | A married couple has **$1.9M** of aggregate business losses and $600k of nonbusiness income in 2026. **What is the 2026 §461(l) EBL threshold (MFJ), in what ORDER do §469 passive limits, §461(l) EBL, and the §172 NOL rules apply, and what happens to the disallowed EBL in the following year?** | {
"base_model": {
"accuracy": {
"mean_score": 3.5,
"n_runs": 2
},
"grounding": {
"mean_score": 1.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F13 | null | Federal | null | A 52-year-old starts a §72(t) Substantially Equal Periodic Payment (SEPP) stream from a $1.4M IRA using the amortization method, then **changes the payment amount in year 3**. **Which modification rules apply, what is the recapture tax (10% plus interest) measured from, when can a one-time switch to the RMD method be m... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F14 | null | Federal | null | A non-spouse beneficiary inherits a **$2.6M** traditional IRA from a decedent whose estate paid federal estate tax. **How is the §691(c) income-tax deduction for estate tax attributable to IRD computed, how is it spread across the SECURE Act 10-year distribution window, and does it interact with the annual RMD-within-t... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 10,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F15 | null | Federal | null | A taxpayer repays **$310,000** of previously reported (and taxed) commission income in 2026 that was included in 2023 income. **When does §1341 apply, how is the "A vs B" computation done, and why can the §1341(a)(5) credit method beat an amended return — and what is the trap if the repayment relates to an obligation t... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F16 | null | Federal | null | A trader holds SPX §1256 contracts against a non-§1256 equity position forming a straddle. **How does the §1092 loss-deferral rule interact with §1256 year-end mark-to-market, what does a §1256(d) election OUT of 60/40 do, and how does a "mixed straddle account" election under Reg. §1.1092(b)-4T change loss timing and ... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 10,
"n_runs": 2
}
},
"ha... |
adversarial | hard_tax_questions_90_F17 | null | Federal | null | A private-equity buyer acquires an S-corp; the parties want a stepped-up asset basis. **When is a §338(h)(10) election available vs a §336(e) election, how does the S-corp's built-in gain and the seller's §1411 exposure differ under each, and what happens to the election if the S election was inadvertently invalid befo... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 10,
"n_runs": 1
}
},
"ha... |
adversarial | hard_tax_questions_90_F18 | null | Federal | null | A taxpayer has **$1,244,000** of pre-tax traditional IRA balances and wants a clean backdoor Roth of $7,500. **Why is the conversion ~99% taxable under the §408(d)(2) aggregation rule, how does rolling the pre-tax IRA into an active 401(k) fix it, and does a SEP-IRA or SIMPLE balance count in the year-end aggregation?*... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F19 | null | Federal | null | In 2026 a participant wants to max the after-tax mega-backdoor Roth: **$24,500 deferral + $8,000 Roth catch-up + employer match + after-tax**. **What is the §415(c) total annual-additions limit for 2026, how do catch-up contributions interact with (or sit outside of) §415(c), and what is the exact after-tax contributio... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_F2 | null | Federal | null | An investor holds two option-income ETFs: one §1256 60/40 fund and one reporting **100% return of capital (ROC)**. ROC has driven the ROC fund's basis to **exactly $0** and more ROC arrives. **How is the *excess* ROC characterized, how does it interact with the §1256 mark-to-market 60/40 split on the sister fund, and w... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F20 | null | Federal | null | A grantor funds an irrevocable trust that is a **GST trust** as defined in §2632(c)(3) but wants to affirmatively elect OUT of automatic allocation for a specific year's transfer. **How does the automatic-allocation default apply to indirect skips, what is the mechanic and deadline to elect out on a timely Form 709, an... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F21 | null | Federal | null | A complex trust terminates in 2026 with **$48,000** of excess deductions (including trustee fees and a §642(c) charitable-set-aside remnant). **After §67(g), which of these excess deductions pass through to beneficiaries under §642(h)(2), how are they characterized (above-the-line vs itemized), and how does the §1.642(... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_F22 | null | Federal | null | A UHNW client wraps a hedge-fund-style portfolio in **Private Placement Life Insurance**. **What §817(h) diversification requirements must the separate account meet, how does the investor-control doctrine (Rev. Rul. 2003-91/2003-92) determine whether the inside build-up is tax-deferred, and what happens if the policy f... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F23 | null | Federal | null | A taxpayer materially participates in a trade or business AND owns rentals that self-rent to that business. **When is self-rental income recharacterized as non-passive and thus excluded from NII under §1411, how does a §469 grouping election affect the §1411 result, and does the §1.469-2(f)(6) self-rental rule override... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"harne... |
adversarial | hard_tax_questions_90_F24 | null | Federal | null | A trader has a **$220,000** net §1256 loss in 2026 after two profitable prior years. **How does the §1256(d) 3-year carryback election work, what is the ordering against prior-year §1256 GAINS only, how is it claimed (Form 1045 vs 1040-X), and how does it interact with any §475(f) mark-to-market election already in eff... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F25 | null | Federal | null | A decedent's gross estate is **$18M**, of which a closely held business is $9.5M. **Does the estate qualify for §6166 installment payment of estate tax (the 35%-of-adjusted-gross-estate test), what is the 2% portion and the deferral/installment schedule, and what acceleration events under §6166(g) terminate the deferra... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F26 | null | Federal | null | An investor contributes an appreciated concentrated stock portfolio to a newly organized ETF in a **§351 exchange**, but the portfolio carries a margin liability exceeding basis. **When is the §351 control requirement met for an ETF seeding, does §357(c) trigger gain because liabilities exceed basis, and how does the §... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F27 | null | Federal | null | A taxpayer sells a security at a loss in a taxable account and repurchases substantially identical shares in their IRA within 30 days. **Does the §1091 wash sale apply across the taxable/IRA boundary, is the disallowed loss added to IRA basis (and thus permanently lost), and how does this differ from a spouse's account... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F28 | null | Federal | null | A taxpayer harvests a crypto loss and instantly rebuys, then separately enters an offsetting short against an appreciated crypto position. **Why does §1091 not currently reach the crypto loss harvest, but could §1259 constructive-sale rules reach the appreciated-position hedge, and what is the specific "appreciated fin... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F29 | null | Federal | null | A rental acquired via a **2023 §1031 exchange** ($500k basis, $425k embedded deferred gain) is converted to a primary residence, then sold after 2 years. **How does the §121(b)(5) nonqualified-use fraction reduce the exclusion, why must the property be owned 5 years total under §121(d)(10), and how is post-May-6-1997 d... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_F3 | null | Federal | null | A founder holds two 2012 QSBS grants in one issuer (**247,399 shares, ~$0.01 basis**) and wants to multiply the §1202 exclusion beyond the personal cap by funding **non-grantor trusts** for a spouse and two children. **How does the cap ("greater of $10M or 10× aggregate adjusted basis") apply per-taxpayer vs per-issuer... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F30 | null | Federal | null | A taxpayer does a §1031 exchange with a **related party**, and the related party sells the relinquished property within **18 months**. **How does §1031(f) disallow the deferral, what is the 2-year holding requirement measured from, and which §1031(f)(2) exceptions (non-tax-avoidance) can preserve deferral?** | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F31 | null | Federal | null | A commercial building with cost-segregated components is sold at a gain. **How is the gain bifurcated among §1245 (full ordinary recapture on personal property), §1250 (ordinary only on excess-over-straight-line), and the 25% unrecaptured §1250 gain rate — and how does bonus depreciation taken on the §1245 components c... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F32 | null | Federal | null | A founder's C-corp becomes worthless; original capitalization was **$1.3M**. **When does §1244 convert the worthless-stock loss from capital to ordinary (and up to what annual dollar cap for MFJ), what are the §1244 qualification requirements at issuance, and how does §165(g) timing (the year of worthlessness) interact... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 10,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F33 | null | Federal | null | An executive receives accelerated equity on an acquisition; the parachute payment is **3.1× the base amount**. **How is the §280G "base amount" (5-year average) computed, at what point does the 3× safe harbor flip to a 20% excise tax under §4999 on the ENTIRE excess-parachute amount, and how does a shareholder-approval... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F34 | null | Federal | null | A parent lends a child **$900,000** at 1% when the AFR is higher, for a home purchase. **How does §7872 impute foregone interest, is this a gift loan or demand loan for the imputation timing, how does the $10,000 de minimis and the $100,000 "net investment income" exceptions apply, and what are the dual gift-tax and in... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 10,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"harn... |
adversarial | hard_tax_questions_90_F35 | null | Federal | null | A **dual US/Australian citizen** resident in the US owns a former primary residence in Australia now rented. **How does US citizenship override any §7701(b) residency test (worldwide taxation regardless of presence), how do the §911 exclusion and Form 1116 FTC interact on the Australian rental, and why does the SALT-le... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 6,
"n_runs": 1
}
},
"harne... |
adversarial | hard_tax_questions_90_F36 | null | Federal | null | A taxpayer claims real-estate-professional status to deduct rental losses against W-2 income while their spouse works full-time elsewhere. **What are the two independent §469(c)(7) tests (>50% of personal services AND >750 hours in real property trades), can spousal hours be combined for the RP test vs the material-par... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_F4 | null | Federal | null | A taxpayer rents their residence to their own S-corp for exactly **14 days** for board meetings at $1,500–$2,500/day, seeking **100% tax-free** rental income under §280A(g) while the S-corp deducts the payment. **What is the precise §280A(g) day-count limit, what happens to BOTH the income exclusion and the corporate d... | {
"base_model": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F5 | null | Federal | null | A business vehicle was **totaled Aug 2023** and replaced **Oct 2023**, but the preparer kept depreciating the destroyed vehicle through 2025 and **no §1033 election appears to have been made**. **What is the §1033 replacement-period deadline for a 2023 involuntary conversion, how is the election made (and can it be mad... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 8,
"n_runs": 1
}
},
"har... |
adversarial | hard_tax_questions_90_F6 | null | Federal | null | A taxpayer sells QSBS held **3 years** (short of the 5-year §1202 hold) at a $4.2M gain and wants to defer under §1045 by reinvesting in new QSBS, but the replacement shares are acquired **through an investment partnership** rather than directly. **What is the §1045 60-day reinvestment window measured from, how does th... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_F7 | null | Federal | null | A taxpayer carries **$7.8M** of aggregate installment obligations outstanding at year-end from a 2025 business sale. **At what threshold does the §453A interest charge kick in, how is the "applicable percentage" computed, which AFR/underpayment rate applies to the deferred tax, and is the §453A interest itself deductib... | {
"base_model": {
"accuracy": {
"mean_score": 4.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_F8 | null | Federal | null | A W-2 taxpayer in a high bracket buys a short-term rental (avg guest stay **≤7 days**) and claims losses against wages by materially participating. **Why does the ≤7-day average stay remove the activity from the §469 "rental activity" definition, which of the seven material-participation tests is realistically availabl... | {
"base_model": {
"accuracy": {
"mean_score": 10,
"n_runs": 1
},
"grounding": {
"mean_score": 7,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
"ha... |
adversarial | hard_tax_questions_90_F9 | null | Federal | null | A partner contributes appreciated real estate (**FMV $3.0M, basis $1.1M**) to an LLC; the property is later depreciated and partially sold. **How does the §704(c) ceiling rule create a distortion, when must the partnership use the traditional-with-curative or remedial method, and how are the built-in gain and depreciat... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 10,
"n_runs": 2
},
"grounding": {
"mean_score": 10,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_FL1 | null | Florida | null | A FL homestead owner's **assessed** value rose 8–14%/yr from 2018–2025 despite the **Save Our Homes** cap (lower of 3% or CPI); 2025 assessed value is overstated by ~**$161,402**. **(a) What is the exact SOH cap and what triggers a lawful "recapture"? (b) How many prior years of over-assessment can be recovered and und... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_FL10 | null | Florida | null | A FL borrower records a **$1,600,000** mortgage. **What is the current nonrecurring 2-mill (0.2%) intangible tax on the mortgage under Ch. 199, is the annual intangibles tax on stocks/bonds still in effect (repealed 2007), and how does the intangible tax combine with the note doc-stamp for total FL closing tax on the f... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_FL2 | null | Florida | null | A FL homeowner sells a homestead with **$420,000** of accumulated Save-Our-Homes benefit and buys a more (or less) expensive home. **How does §193.155(8) portability transfer the SOH differential (up to the $500,000 cap), how is the "upsizing" vs "downsizing" calculation different, and what is the deadline (assessment-... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 4.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_FL3 | null | Florida | null | A FL real-estate transfer involves a **$925,000** deed and a purchase-money note. **What is the documentary stamp tax rate on the deed (and the Miami-Dade surtax difference), what is the separate doc-stamp rate on the promissory note plus the nonrecurring intangible tax on the mortgage, and does an UNrecorded note stil... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_FL4 | null | Florida | null | A FL C-corp has federal bonus depreciation and a federal NOL. **How does FL's §220 corporate income tax piggyback on federal taxable income, how does FL decouple from federal bonus depreciation (the addback + subsequent-year subtraction), and how is the FL NOL carryforward computed differently from the federal §172 NOL... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_FL5 | null | Florida | null | A FL business (or rental owner) holds furniture/equipment. **Who must file the annual TPP return (DR-405) by April 1, how does the $25,000 TPP exemption apply per return/site, what is the penalty for failure to file (loss of the exemption + penalties), and are STR furnishings TPP-taxable?** | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_FL6 | null | Florida | null | A FL homeowner rents a property for stays under 6 months (STR). **What combined transient-rental taxes apply (6% state sales tax + county Tourist Development Tax, e.g., 5% in Collier), who is responsible for collection when a platform (Airbnb/VRBO) is involved, and how does the 6-month threshold define a taxable "trans... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 6,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_FL7 | null | Florida | null | A FL homestead's market value falls, then rises; its capped assessed value is below market. **How does the §193.155 recapture rule REQUIRE the assessor to raise the assessed value by up to 3% (or CPI) even in a year market value is flat or falling, why is that not a violation of Save Our Homes, and when does a change/i... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 2,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_FL8 | null | Florida | null | A recent FL transplant files bankruptcy with a **$2.1M** FL homestead. **How does FL's unlimited constitutional homestead creditor exemption interact with the federal Bankruptcy Code §522(p) $189,050 (indexed) cap for homesteads acquired within 1,215 days, and does the acreage limit (½ acre municipal / 160 acres rural)... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_FL9 | null | Florida | null | A FL property is held in a **Florida land trust** nested for privacy, later converted to a primary residence. **Does titling in a land trust or a single-member LLC preserve or destroy the FL homestead exemption and its creditor protection, why must an LLC be dissolved before claiming homestead, and how is the exemption... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"harne... |
adversarial | hard_tax_questions_90_NC1 | null | North Carolina | null | An NC resident funds an **irrevocable non-grantor trust with NC situs** (marketed for 1,000-year dynasty use) that retains option-income-ETF distributions during beneficiaries' Kiddie-Tax years. **At what flat rate does NC tax income *retained* by the trust vs *distributed*, on what basis does NC assert jurisdiction ov... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_NC10 | null | North Carolina | null | An NC taxpayer claims the federal §199A 20% QBI deduction. **Does NC allow the §199A deduction in computing NC taxable income, given NC starts from federal AGI (not taxable income) and applies its own standard/itemized deductions — and what is the net effect on the NC base?** | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 10,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"ha... |
adversarial | hard_tax_questions_90_NC11 | null | North Carolina | null | A trust is marketed as an NC dynasty trust "up to ~1,000 years." **Has NC repealed/modified the common-law Rule Against Perpetuities to permit multi-century trusts, what statutory duration limit (if any) applies under NC's Uniform Statutory RAP, and how does the federal GST exemption interact with a perpetual NC trust ... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 5,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_NC2 | null | North Carolina | null | An NC taxpayer claims **federal bonus depreciation and §179** on business assets. **How does NC require an 85% addback of the federal bonus/§179 excess in year one, over how many subsequent years is the addback deducted (the 20%-per-year spread), and how does this create a permanent NC/federal basis divergence on dispo... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8,
"n_runs": 1
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NC3 | null | North Carolina | null | An NC resident earns pass-through income taxed by another state that also imposed a PTE tax. **How is the §105-153.9 out-of-state credit computed (the lesser-of limitation), does NC allow the credit for entity-level PTE taxes paid by the pass-through (vs only owner-level taxes), and how does the credit interact with NC... | {
"base_model": {
"accuracy": {
"mean_score": 3.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_NC4 | null | North Carolina | null | An NC S-corp makes the **Taxed PTE** election. **How is the NC PTE tax base computed for resident vs nonresident owners, why must NC-resident owners include their entire pro-rata share (not just NC-source), and how does the electing entity's owners claim the corresponding NC credit to avoid double tax?** | {
"base_model": {
"accuracy": {
"mean_score": 3,
"n_runs": 2
},
"grounding": {
"mean_score": 1.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_NC5 | null | North Carolina | null | An NC S-corporation has **$4.2M** net worth. **How is the NC franchise tax computed under §105-122 (the net-worth/investment-in-tangible-property/appraised-value bases), what is the minimum franchise tax, and does S-corp status exempt the entity from the franchise tax (it does not)?** | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"harne... |
adversarial | hard_tax_questions_90_NC6 | null | North Carolina | null | A federal tax change is enacted mid-year 2026. **Does NC automatically conform under a rolling date or does §105-228.90 fix conformity to a static IRC date, how does that create differences for provisions like §174 R&E capitalization, and what addback/subtraction is required on the NC return in a nonconformity year?** | {
"base_model": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"har... |
adversarial | hard_tax_questions_90_NC7 | null | North Carolina | null | An NC-based service company earns receipts from out-of-state customers. **Under NC's market-based sourcing in §105-130.4, is the service receipt sourced to where the benefit is received, how are the cascading throwout/reasonable-approximation rules applied when the benefit location is unknown, and how does this differ ... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NC8 | null | North Carolina | null | An NC dynasty trust retains ETF income during beneficiaries' minor years to avoid Kiddie Tax. **Does trapping income at the trust level (compressed §1(e) brackets) actually beat the child paying at §1(g) parent rates, at what income does the trust hit the top 37% bracket + NIIT, and how does the NC 3.99% flat rate chan... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 1
},
"grounding": {
"mean_score": 10,
"n_runs": 1
}
},
"... |
adversarial | hard_tax_questions_90_NC9 | null | North Carolina | null | An NC pass-through has nonresident owners. **When must the entity withhold NC tax on nonresident distributive shares, when can it instead file a composite return, and how does the Taxed PTE election eliminate the withholding requirement — and what happens to a nonresident who also files individually?** | {
"base_model": {
"accuracy": {
"mean_score": 5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_NY1 | null | New York | null | An employer's MCTD covered-employee payroll exceeds **$312,500** in a quarter. A Manhattan-based corporate trainer spends **three weeks/month training outside the MCTD**; the employer is a **PrompTax** filer. **(a) Applying the four ordered allocation tests, is the trainer a covered employee whose entire payroll is sub... | {
"base_model": {
"accuracy": {
"mean_score": 4,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 10,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"ha... |
adversarial | hard_tax_questions_90_NY10 | null | New York | null | A taxpayer owes NY State **$180,000** and wants an Offer in Compromise. **What are the NY OIC eligibility grounds (doubt as to collectibility/liability/undue economic hardship), why does an accepted OIC of a fixed and final liability over $100,000 require NYS Supreme Court approval, and how does that differ from the IR... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NY11 | null | New York | null | A nonresident sells an interest in an entity that owns NY real property. **Under §631/§632 and the "NY-source" rules, is the gain on the sale of the ENTITY interest NY-source (look-through to NY real property under §631(b)(1)(A)), how is it allocated on Form IT-203, and how does the §453 installment method affect the N... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_NY2 | null | New York | null | A person domiciled elsewhere keeps a NYC apartment and spends **184 days** partly in NY, including days of only a few hours. **How does NY's statutory-residence test (§605(b)(1)(B)) count a "day" (any part of a day, with narrow exceptions), what qualifies as a "permanent place of abode" after *Matter of Gaied*, and doe... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NY3 | null | New York | null | A nonresident employee of a NY employer works remotely from another state **for their own convenience** (not employer necessity). **Under NY's convenience-of-the-employer rule, are those remote workdays sourced to NY (taxable) anyway, what narrow "bona fide employer office" exceptions exist, and how does this create do... | {
"base_model": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NY4 | null | New York | null | A NY employer files quarterly **Form NYS-45**. **What is the 2026 NY State Unemployment Insurance taxable wage base per employee, how is the UI contribution vs the reemployment-service fund and the withholding reconciliation reported on one NYS-45, and how does a change in the experience rate affect quarter-by-quarter ... | {
"base_model": {
"accuracy": {
"mean_score": 3,
"n_runs": 2
},
"grounding": {
"mean_score": 1,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NY5 | null | New York | null | A taxpayer changes NY residency mid-year while holding installment obligations and deferred comp. **How does Tax Law §638/§639 require accrual of certain items on a change of residence, which items are subject to the accrual (and which can elect out with a bond), and how does this interact with the part-year IT-203 all... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_NY6 | null | New York | null | A NYC S-corp real-estate brokerage wants both the **NYS PTET and NYC PTET**. **What are the annual election deadlines (March 15, no extension), how do the NYS and NYC PTET estimated-payment schedules differ from federal estimates, and what happens to the SALT-cap benefit if the election is made but estimates are underp... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_NY7 | null | New York | null | A NYC resident operates a consulting practice through a single-member LLC. **Is the practice subject to the 4% NYC UBT, how does the UBT self-employment/§services carve-out (the "personal services" exemption) apply, what is the UBT credit against NYC personal income tax, and how does the UBT base differ from federal SE... | {
"base_model": {
"accuracy": {
"mean_score": 5,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 4,
"n_runs": 1
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_NY8 | null | New York | null | A NY-resident estate is **$7.5M** against a ~$7.16M NY exemption. **How does the NY estate-tax "cliff" work (the exemption phases out entirely between 100% and 105% of the exemption), what is the marginal effective tax rate on the dollars inside the cliff (can exceed 100%), and how does the 3-year gift add-back interac... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 2,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 4,
"n_runs": 2
},
"grounding": {
"mean_score": 2,
"n_runs": 2
}
},
"harne... |
adversarial | hard_tax_questions_90_NY9 | null | New York | null | A business consumes diesel/motor fuel in a nontaxable manner and seeks a **Petroleum Business Tax reimbursement**. **Which forms (e.g., AU-630) claim the PBT reimbursement, what uses qualify (e.g., commercial gallonage, farming, government), what is the claim deadline/statute of limitations, and how does the reimbursem... | {
"base_model": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_TX1 | null | Texas | null | A Texas family forms **Olive Tree Holding Company, LLC (taxed as an S-corp)** and holds a partnership-classified holding LLC and a C-corp (Epic Software Group, Inc.), assuming "no income tax, nothing to file." **Which entities are "taxable entities" for the margin tax, how does federal S/partnership/C classification in... | {
"base_model": {
"accuracy": {
"mean_score": 4.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_TX10 | null | Texas | null | A Texas tiered partnership structure passes total revenue up from a lower-tier to an upper-tier entity. **How does the §171.1015 tiered-partnership provision let the lower tier exclude revenue passed to the upper tier, what election/report is required, and how does it prevent double-counting of the same revenue in the ... | {
"base_model": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 5.5,
"n_runs": 2
},
"grounding": {
"mean_score": 2,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_TX11 | null | Texas | null | A Texas business owner wants a pass-through-entity-tax (PTET) SALT-cap workaround like CA/NY offer. **Why is a PTET workaround structurally unavailable/unhelpful in Texas (no personal income tax to credit), does the margin tax qualify as a deductible entity-level tax for the federal SALT workaround under Notice 2020-75... | {
"base_model": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9,
"n_runs": 2
}
},
"harne... |
adversarial | hard_tax_questions_90_TX2 | null | Texas | null | A Texas LLC computes taxable margin and must choose a deduction method. **How is the margin base computed as the lesser of 70% of total revenue, revenue minus COGS (§171.1012), or revenue minus compensation (§171.1013), which industries are barred from the COGS method (e.g., service providers), and is the election annu... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_TX3 | null | Texas | null | A Texas holding LLC receives 92% of its gross income from dividends, interest, and capital gains. **Does it qualify as a "passive entity" under §171.0002 and thus escape the margin tax, why does the entity type (partnership/trust vs LLC) matter for the exception, and must it still file to claim passive status?** | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_TX4 | null | Texas | null | Several commonly controlled Texas entities operate as a unitary business. **When must they file a combined group report under §171.1014, how is the >50% controlling-interest test applied, how is the group's margin and single sales factor computed, and how are inter-member eliminations handled?** | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 1
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_90_TX5 | null | Texas | null | A Texas LLC has total revenue **below** the no-tax-due threshold. **Must it still file a Public Information Report (PIR) and/or a No Tax Due Report, what is the consequence (forfeiture of charter and loss of liability shield) for failing to file even when zero tax is owed, and how is the forfeiture cured?** | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_TX6 | null | Texas | null | A Texas **series LLC** operates multiple protected series. **Is each series a separate taxable entity for the margin tax or is the parent the single reporting entity, how does the Comptroller treat the series for combined reporting, and what are the registration/assumed-name consequences?** | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 1
},
"grounding": {
"mean_score": 5.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_90_TX7 | null | Texas | null | A Texas entity with total revenue of **$18M** considers the E-Z computation. **What is the total-revenue ceiling to use the E-Z computation, what is the E-Z rate, why is the E-Z method usually worse than the standard margin computation for a low-margin business, and can COGS/compensation be deducted under E-Z?** | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_TX8 | null | Texas | null | A Texas entity sells services to customers in multiple states. **How is the Texas single gross-receipts (sales) factor sourced for services (market-based location of receipt), why does Texas have NO throwback rule (so "nowhere" sales escape), and how did the *Sirius XM* decision reshape service-receipt sourcing?** | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 3.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_90_TX9 | null | Texas | null | A Texas LLC taxed federally as an S-corp assumes its pass-through status carries to Texas. **Why does Texas ignore the federal S-election for margin-tax purposes, is the margin computed on entity revenue regardless of shareholder-level pass-through, and does shareholder compensation get a §171.1013 deduction?** | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_final10_Q100 | null | Mixed | null | A Florida business (or high-net-worth household with a home-office media/telecom setup) buys a **$4,000/mo** bundled package combining streaming video, VoIP telephone, and internet access from a single provider. **Under Florida's Communications Services Tax (Ch. 202), which components of the bundle are subject to the s... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 1
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_final10_Q91 | null | Mixed | null | A software company claims a **$1,480,000** §41 research credit in 2026 while also being subject to mandatory **§174 capitalization/amortization** of specified research expenditures (5-year domestic / 15-year foreign). The company did **not** make the §280C(c)(2) reduced-credit election and instead intends to claim the ... | {
"base_model": {
"accuracy": {
"mean_score": 4,
"n_runs": 2
},
"grounding": {
"mean_score": 3,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"har... |
adversarial | hard_tax_questions_final10_Q92 | null | Mixed | null | A U.S. taxpayer bought a home in the U.K. in 2019 financed with a **£600,000** GBP-denominated mortgage. In 2026 the taxpayer refinances/pays off the mortgage when the USD has strengthened materially against GBP, so the dollar cost to extinguish the debt is **lower** than the dollar value borrowed. **Does the taxpayer ... | {
"base_model": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_final10_Q93 | null | Mixed | null | A taxpayer settles **$820,000** of recourse business debt for $300,000 in 2026. Immediately before the discharge the taxpayer is insolvent by **$540,000** (liabilities exceed FMV of assets by that amount). The taxpayer has an NOL carryforward, general business credit carryforwards, capital loss carryforwards, and depre... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9,
"n_runs": 2
},
"grounding": {
"mean_score": 9.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_final10_Q94 | null | Mixed | null | An active options/equities trader had a **$430,000** net trading loss in 2026 and wants ordinary-loss (not capital-loss-limited) treatment plus wash-sale relief. They did **not** file a §475(f) mark-to-market election statement by the prior-year due date. **When exactly must the §475(f) election have been made to be ef... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 1
},
"grounding": {
"mean_score": 4,
"n_runs": 1
}
},
"data_store": {
"accuracy": {
"mean_score": 10,
"n_runs": 1
},
"grounding": {
"mean_score": 9,
"n_runs": 1
}
},
"harn... |
adversarial | hard_tax_questions_final10_Q95 | null | Mixed | null | A taxpayer sells marketable securities at a **$260,000** loss to (a) their wholly owned S-corporation, and separately sells other securities at a loss to (b) a partnership in which the taxpayer owns a **55%** capital-and-profits interest, then within 25 days the taxpayer repurchases substantially identical securities i... | {
"base_model": {
"accuracy": {
"mean_score": 8.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 9.5,
"n_runs": 2
},
"grounding": {
"mean_score": 8.5,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_final10_Q96 | null | Mixed | null | A non-grantor trust (administered outside California, with a non-CA trustee) **accumulated** income in years 2021–2024 during which its sole noncontingent beneficiary was a nonresident, so no California tax was paid on the accumulated income. In 2026 the trust makes a **$1,900,000** accumulation distribution to that be... | {
"base_model": {
"accuracy": {
"mean_score": 4,
"n_runs": 2
},
"grounding": {
"mean_score": 2.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 4.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_final10_Q97 | null | Mixed | null | A Texas-based company sells a **$3,000,000/yr** cloud software subscription (SaaS) to Texas customers and assumes "Texas has no income tax and SaaS is intangible, so it's not taxable." **Under Texas Tax Code §151.0035 and Comptroller Rule 3.330, is SaaS taxed as a "data processing service," what portion of the charge i... | {
"base_model": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 6.5,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 4,
"n_runs": 2
}
},
... |
adversarial | hard_tax_questions_final10_Q98 | null | Mixed | null | A non-grantor trust has income of **$700,000**, one North Carolina resident beneficiary and two nonresident beneficiaries, and the trust itself has no other NC connection. **After the post-*Kaestner* constitutional limits, how does N.C. Gen. Stat. §105-160.2 now apportion the trust's taxable income to North Carolina ba... | {
"base_model": {
"accuracy": {
"mean_score": 8,
"n_runs": 2
},
"grounding": {
"mean_score": 8,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 6.5,
"n_runs": 2
},
"grounding": {
"mean_score": 7.5,
"n_runs": 2
}
},
"h... |
adversarial | hard_tax_questions_final10_Q99 | null | Mixed | null | A New York taxpayer places **$2,200,000** of qualifying property in service in 2026 and claims **federal 40% bonus depreciation** under IRC §168(k) (plus §179). New York has **decoupled** from federal bonus depreciation (other than for certain resurgence-zone / limited exceptions). **On the NY return, how does Tax Law ... | {
"base_model": {
"accuracy": {
"mean_score": 6,
"n_runs": 1
},
"grounding": {
"mean_score": 7,
"n_runs": 2
}
},
"data_store": {
"accuracy": {
"mean_score": 7.5,
"n_runs": 2
},
"grounding": {
"mean_score": 5,
"n_runs": 2
}
},
"har... |
End of preview. Expand in Data Studio
Silvia Tax Bench (v1.0)
200 expert-level U.S. tax questions for evaluating LLM tax guidance, released by CFO Silvia. Two complementary distributions:
- adversarial (100): statutory fine print, current-year figures, multi-provision interactions, and state non-conformity — authored to defeat parametric model knowledge.
- client_scenarios (100): realistic client-planning scenarios with a structured taxpayer persona (filing status, income, balance-sheet bands) and a planning question, representative of production usage.
Each record includes per-configuration aggregate judge scores from the published two-run benchmark study (base model / proprietary tax data store / web search / full harness; 1–10 blind-judge scale for factual accuracy and grounding in primary authority).
Schema
| field | description |
|---|---|
id |
stable question identifier |
benchmark |
adversarial or client_scenarios |
jurisdiction |
Federal or U.S. state the question turns on |
prompt |
the question / scenario text (verbatim, human-screened) |
instructions |
scenario answering instructions (client_scenarios only) |
persona |
structured taxpayer profile (client_scenarios only; see anonymization) |
scores |
per-configuration aggregate judge scores across runs |
Coverage
| benchmark | jurisdiction | n |
|---|---|---|
| adversarial | California | 11 |
| adversarial | Federal | 36 |
| adversarial | Florida | 10 |
| adversarial | Mixed | 10 |
| adversarial | New York | 11 |
| adversarial | North Carolina | 11 |
| adversarial | Texas | 11 |
| client_scenarios | CA | 14 |
| client_scenarios | FL | 17 |
| client_scenarios | NC | 8 |
| client_scenarios | NY | 18 |
| client_scenarios | TX | 30 |
| client_scenarios | Texas | 13 |
Anonymization
Personas are synthetic taxpayer profiles. As an additional safeguard, released persona fields are programmatically coarsened relative to the values used at evaluation time: dollar amounts rounded to two significant figures, rates to one decimal, ages to five-year bands; city and internal system fields removed. Prompt text is released verbatim. The transformation is deterministic and versioned with the benchmark harness.
Provenance & scoring
Answers were produced by a frontier model under four tool configurations in
isolated sessions across two independent runs; every answer was scored 1–10 by
a blind LLM judge required to verify claims against primary tax authority
(statutes, Treasury regulations, IRS publications) for the correct tax year.
scores.*.mean_score averages the runs that judged the item
(n_runs ∈ {1, 2}). Methodology, statistics, and limitations are documented
in the accompanying meta-analysis.
Citation
If you use this benchmark, please cite: CFO Silvia — Retrieval Tooling and the Reliability of LLM Tax Guidance (2026).
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