M&A Advisory in Kentucky
Kentucky's UPS Worldport in Louisville — the world's largest automated package hub at 5.2M sq ft and 12,000 workers — anchors a $280B+ economy that also produces ~95% of the world's bourbon, hosts Toyota's largest global plant in Georgetown, and sits at the crossroads of five major capital markets within a day's drive.
Kentucky's M&A Economy
Kentucky's 2025–2026 LMM market maintained steady 6.0x–7.5x EBITDA valuations despite national volume headwinds, with premiums in healthcare (8.3x), business services (7.5x), and distribution (7.0x). State GDP reached approximately $305B–$315B nominal (FRED recorded $311.07B annualized Q2 2025), with ~115,000–120,000 employer establishments and an estimated 7,000–9,000 LMM-eligible businesses. The KY Cabinet for Economic Development reported 2025 as the second-highest year ever for announced private-sector investment, with 49 manufacturing projects totaling $4.4B+ across 185 location and expansion announcements. Kentucky's structural M&A advantages are unusually concentrated. Louisville's UPS Worldport (5.2M sq ft, 12,000 workers) anchors the Western Hemisphere's premier air cargo hub; CVG in Northern KY serves as Amazon Air's global hub and DHL Americas hub. Toyota Georgetown is the company's largest global plant at 9,950 workers and 550,000-vehicle capacity — backed by $26.1B in announced automotive investment since 2014 and 100+ in-state Toyota suppliers. The bourbon/spirits cluster produces ~95% of world bourbon with a record $10.6B economic engine and 17.1M barrels aging across 125 licensed distilleries. Lexington-based MiddleGround Capital ($4.1B AUM) is the dominant industrial PE sponsor, while Louisville anchors the "aging care capital" ecosystem with Humana, ScionHealth, and Kindred HQs. Succession pressure is acute — 50%+ of KY LMM owners are baby boomers nearing retirement — and strategic proximity to Cincinnati, Nashville, Indianapolis, Chicago, and St. Louis delivers a deep cross-border buyer pool.
Kentucky at a Glance
Key Markets in Kentucky
Louisville / Jefferson County MSA (KY-IN)
Kentucky's largest economic engine, anchored by UPS Worldport, GE Appliances ($12.8B GDP contribution in 2024; $3B new investment announced 2025), Ford LAP ($1.9B EV investment, 2,200 jobs), Humana, Brown-Forman, and ScionHealth. Louisville is simultaneously the bourbon headquarters, the air cargo capital of the Western Hemisphere, and the "aging care capital of America" — a combination no neighboring state can replicate. Heaviest LMM deal flow in bourbon-adjacent, food & beverage, aging care, and 3PL sub-sectors.
Lexington-Fayette MSA
"Horse Capital of the World" and home to Toyota Georgetown (~8,000 employees; Toyota's largest global operation), the University of Kentucky, and Lexmark. MiddleGround Capital ($4.1B AUM) is headquartered here, making Lexington the highest-density PE sponsor city per capita in Kentucky. The Keeneland complex and Bluegrass equine economy generate scarcity-premium M&A unavailable anywhere else in the country. Strong cross-pollination between auto suppliers, equine vets, and UK healthcare services.
Northern Kentucky (Cincinnati MSA — Boone/Kenton/Campbell)
Part of Greater Cincinnati, Northern Kentucky punches above its weight in M&A deal flow because CVG Airport is Amazon Air's global hub and DHL Americas hub, driving logistics, e-commerce fulfillment, and aerospace M&A. Substantial cross-border KY/OH deal activity — Northern KY businesses access Cincinnati's much deeper PE bench (HGGC, Riverside Company, Comvest) while benefiting from Kentucky's lower 4.0%/3.5% individual income tax versus Ohio's higher combined rates.
Bowling Green MSA
Kentucky's fastest-growing metro, home to GM's Corvette Assembly, Fruit of the Loom HQ, and AESC's $2B/2,000-job EV battery gigafactory. The city is transforming from a traditional auto manufacturing center into an EV battery and advanced materials hub — a dynamic that attracts tier-2 chemical, materials, and logistics suppliers seeking proximity to both the assembly plant and the battery gigafactory within a single-day supply chain radius.
How Does Kentucky Compare?
Kentucky M&A benchmarks vs. neighboring states.
Kentucky Deal Landscape 2025-2026
Kentucky's 2025–2026 M&A environment reflects a bifurcated middle market: record activity in bourbon consolidation, equine, automotive, and industrial sectors alongside distressed opportunities in craft spirits and legacy coal. MiddleGround Capital grew AUM from $2.0B to $4.1B between 2023 and 2025, completing multiple platform investments and exits including the Lindsay Precast sale to TJC. Strategics including Humana, Brown-Forman, Sazerac, Heaven Hill, and Churchill Downs drove marquee transactions. Nationally, middle-market multiples averaged 7.2x in H1 2025 (GF Data), with PE paying ~12.0x versus strategics at 8.6–9.8x (Capstone Q3 2025). Kentucky bourbon, equine, and healthcare assets frequently price above state averages on scarcity value. Headwinds include bourbon oversupply ($10B aging inventory / $75M ad valorem barrel tax) and tariff uncertainty on exports.
Bourbon Rebalancing Fuels Distressed M&A Wave
The speculative 2018–2023 bourbon bubble burst; distillery bankruptcies (Garrard County, Luca Mariano, Kentucky Owl) are fueling strategic rollups. Sazerac's Tom Collins Distilling LLC bought Garrard's $26M Truist debt (Feb. 2026); Brown-Forman restructured 12% of its 5,400-person workforce and closed its Louisville Cooperage in Jan. 2025; Pernod Ricard entered merger talks with Brown-Forman (March 2026). Kentucky barrels sit at a record 17.1M — aging tax has surged 163% over five years to $75M, suppressing sub-scale craft distillery cash flows and accelerating distressed exits.
MiddleGround-Led Industrial Roll-Ups Redefine Kentucky PE
Lexington-based MiddleGround Capital grew AUM from $2.0B to $4.1B between 2023 and 2025, completing Zoerkler (May 2025), Pi Innovo add-on (Feb. 2026), and the Lindsay Precast sale to TJC ($30.9B AUM, Dec. 2025). MiddleGround has made 48 platform and add-on investments and 6 exits — anchoring Kentucky's industrial PE presence across automotive tier suppliers, precast concrete, and B2B services. TJC's acquisition of Lindsay Precast explicitly cited data-center and utility infrastructure end markets.
Humana-Anchored Value-Based Care Drives Healthcare Consolidation
Humana's CenterWell platform (Welsh Carson JV) continues rapid buildout with FY25 patient-growth guidance of 50,000–70,000 net adds (+15%). Kentucky behavioral health and autism services saw >35% YoY Q1 2025 deal-flow increases (PwC), and PE participation in healthcare deals rose to 40.2% of sector capital (RL Hulett), substantially higher than 2024's 25.1%. Louisville-based advisory bench includes Stout Risius Ross, Lincoln International, and regional boutiques serving a dense cluster of aging-care platforms.
Data-Center Energy Demand Repositions Eastern KY Land Assets
LG&E/KU filed for $3.7B in new and upgraded power plants to serve data-center demand; Range Impact acquired two eastern Kentucky coal-mine complexes (Dec. 31, 2025) totaling ~30,000 surface acres / 150,000 mineral acres to reposition for energy and renewable projects; Rye Development is advancing 2,128 MWh of pumped hydro on former Bell County coal land. This infrastructure repositioning creates new M&A categories — mine-to-data-center conversions, pumped storage, and grid-scale battery projects — with buyers from utilities, tech hyperscalers, and infrastructure PE.
Exit Preparation Timeline
A practical roadmap for Kentucky business owners planning an exit.
- Evaluate entity form and model Form 740-PTET election (irrevocable once made on a timely-filed return; election made annually by an authorized person; creates SALT-cap workaround at 4.0%/3.5% for 2025/2026) versus passing through to individual 740s — on a $80M–$100M gain, the federal SALT benefit of the PTET election alone can exceed $1M.
- For family-owned businesses, model Kentucky's KRS Chapter 140 inheritance tax exposure — channel ownership to Class A beneficiaries (spouse, children, grandchildren, siblings; fully exempt) before the sale and consider GRATs, IDGTs, and Kentucky LLC discount planning to avoid Class B (4%–16%) or Class C (6%–16%) rates on non-lineal or non-family heirs; Form 92A200 is due within 18 months of any qualifying death.
- Engage a sell-side accounting advisor (FORVIS Mazars Louisville/Lexington, MarksNelson, BDO, or RSM) for 36-month quality-of-earnings normalizing owner compensation, LLET minimums (KRS 141.0401: lesser of $0.095/$100 gross receipts or $0.75/$100 gross profits, $175 floor, never creditable against 5% income tax), and one-time items; begin financial statement preparation.
- Inventory active KBI (Kentucky Business Investment), KEIA (Kentucky Enterprise Initiative Act), KRA, and KAITC (Kentucky Angel Investment Tax Credit) incentive agreements with KEDFA — confirm transferability, recapture conditions, and advance-consent requirements; quantify these credits as potential deal-value levers worth 2–10% of EV.
- Run internal sales/use tax, withholding, and LLET compliance review; consider KDOR Voluntary Disclosure Agreement (4-year lookback) if exposure exists — successor liability applies under KRS 139.670/139.680 and a buyer can be personally liable for unpaid sales/use tax absent a KDOR tax clearance letter.
- Confirm Kentucky ABC distiller/rectifier/wholesaler licenses, TTB permits (DSP, Basic Permit), and KYDEP environmental permits are current; for equine assets, verify Kentucky Horse Racing and Gaming Corporation license transferability requirements and Churchill Downs change-of-control consent mechanics.
- Obtain third-party appraisals on Kentucky real property, rickhouse assets, and aging bourbon barrel inventory for purchase price allocation and inheritance tax valuation discounts — barrel-by-barrel inventory audit reconciled to TTB monthly reports is standard buyer expectation; rickhouse property tax treatment under the bourbon barrel ad valorem tax phase-out (HB 5, 2023) must be preserved without triggering reassessment.
- Engage an investment banker with deep KY buyer relationships spanning Sazerac, Heaven Hill, Brown-Forman, Beam Suntory, Pernod Ricard for spirits deals; MiddleGround Capital, TJC, and industrial PE platforms for manufacturing; and Welsh Carson, KKR, or Bain Capital for healthcare targets — the named buyer pool in each sector is small, relationship-driven, and sector-specific.
- Launch teaser and CIM; for bourbon/spirits deals, build a curated buyer list of 18–25 strategic conglomerates and PE platforms, avoiding broad auctions that risk confidentiality in the small Bardstown/Frankfort/Louisville bourbon community; distribute Form 740-PTET analysis alongside purchase price allocation modeling showing 6% sales tax on tangible assets and successor-liability escrow requirements.
- Populate data room with Form 740-PTET filings, 720/PTE/725/LLET returns, Forms 92A200 (if any estate events), KEDFA incentive agreements (KBI/KEIA/KAITC), ABC and TTB files, barrel inventory schedules by vintage, rickhouse property tax records, and UCC/lien searches.
- Run side-by-side asset vs. stock sale models incorporating 6% Kentucky sales tax on tangible personal property, KDOR tax clearance escrow mechanics, 338(h)(10)/336(e) elections, and PTET stub-period toggle — quantify the federal SALT deduction benefit of the irrevocable PTET election for the transaction year.
- Secure KEDFA written consent to KBI/KEIA/KRA/KAITC credit assignments before signing — these credits require advance approval and may represent 2–10% of enterprise value; coordinate with local TIF authorities and confirm post-closing KEIA compliance obligations for equipment placed in service.
- Submit KDOR sales/use tax clearance letter request at signing per KRS 139.670/139.680; negotiate escrow release (typically 30–90 day hold) tied to clearance — absent the letter, the buyer is personally liable for the seller's unpaid sales/use taxes as a matter of statute, not just contract.
- Execute Kentucky ABC license transfers (minimum 60-day review; no license issues until 30 days after mandatory newspaper publication under KRS 243.360; transitional license under KRS 243.045 covers up to 90 days) and TTB DSP change-of-proprietorship filings — for bourbon transactions, build a 60–90 day regulatory bridge with pre-cleared transition licenses.
- Make Form 740-PTET election for the stub period (irrevocable; creates the SALT-cap federal deduction); issue Forms PTET-CR to all electing owners; for any deceased-owner sale, coordinate Form 92A200 within 18 months and capture the 9-month 5% discount on inheritance tax payments exceeding $5,000.
- File Kentucky SOS articles of merger/amendment/withdrawal; close, execute post-closing escrow and working capital true-up; confirm KEDFA post-closing compliance obligations on transferred KBI/KEIA incentive agreements; coordinate LLET final-period returns and stub-period K-1/PTET-CR distribution to investors.
Why Kentucky Business Owners Choose Ad Astra
Local market knowledge and national buyer networks — the combination that drives premium outcomes for Kentucky business owners.
Schedule a ConsultationKentucky Bourbon & Spirits Network
Ad Astra maintains direct relationships with the Louisville-, Frankfort-, and Bardstown-headquartered strategics most active in Kentucky bourbon — Sazerac, Brown-Forman, Heaven Hill, Beam Suntory, Wild Turkey/Campari, and Bardstown Bourbon Co. (Pritzker Private Capital) — plus craft-focused PE platforms and family offices. We navigate the TTB Basic Permit and Distilled Spirits Plant change-of-proprietorship (60–120+ days), the Kentucky ABC license transfer under KRS Chapter 243 including the mandatory 30-day newspaper publication under KRS 243.360, KDEP wastewater/stillage permits, and barrel-by-barrel aging inventory diligence reconciled to TTB monthly reports.
MiddleGround / Automotive Tier Supplier Access
We work within the MiddleGround Capital ($4.1B AUM, Lexington) network and the broader 100+ Toyota supplier ecosystem anchored by TMMK Georgetown. Our team understands IATF 16949 quality regimes, PPAP documentation, EV-battery supply-chain transitions, and KEIA/KBI incentive preservation for manufacturing targets. We run competitive processes reaching strategic OEM acquirers, tier-1 consolidators, and MiddleGround-adjacent industrial PE platforms whose investment criteria and management expectations differ materially from generalist sponsors.
Kentucky Tax & Inheritance Planning Expertise
We offer real-time fluency with Kentucky's 4.0%/3.5% flat individual income tax (HB 1, 2025), the Form 740-PTET election mechanics (irrevocable, SALT-cap workaround, due April 15/Oct. 15), the Limited Liability Entity Tax (LLET under KRS 141.0401), and KDOR sales/use tax clearance under KRS 139.670/139.680 predecessor-liability release. Critically, we plan around Kentucky's inheritance tax (KRS Chapter 140) — one of only five states with this tax — structuring ownership to favor Class A beneficiaries (fully exempt: spouse, children, siblings) and avoiding the 4%–16% Class B/C rates on non-lineal heirs.
UPS Worldport & CVG Logistics Buyer Pool
Louisville is the air cargo capital of the Western Hemisphere — UPS Worldport and CVG together serve as the global hubs for UPS, Amazon Air, and DHL, creating one of the deepest logistics and e-commerce fulfillment buyer pools in the country. We access strategic acquirers, 3PL consolidators, and infrastructure PE platforms (Stonepeak, GIP, Macquarie) pursuing last-mile, cold-chain pharma, and freight-forwarding platforms in the corridor. Northern KY/Cincinnati MSA buyers add OH-based PE funds (Riverside, HGGC, Comvest) that routinely cross state lines for quality Kentucky logistics assets.
Kentucky M&A Activity Highlights
Sazerac's Tom Collins Distilling LLC acquired Truist Bank's $26M loan position on bankrupt Garrard County Distilling (Feb. 11, 2026), complementing Sazerac's announced $1B Campbellsville/Laurel expansion — signaling the bourbon giant's aggressive distressed roll-up strategy.
MiddleGround Capital (Lexington) closed the sale of Lindsay Precast to TJC ($30.9B AUM) on Dec. 17, 2025; MiddleGround now manages $4.1B from its Lexington HQ — making it Kentucky's dominant industrial PE sponsor.
Toyota Motor Manufacturing Kentucky announced a $204.4M Georgetown expansion creating 82 jobs (Nov. 20, 2025), part of a $912M multistate Toyota hybrid-production commitment; TMMK remains Toyota's largest global plant at 9,950 workers and 550,000-vehicle capacity.
Keeneland September Yearling Sale (Sept. 2025) set a world record at $531.5M gross (+24% YoY), with 3,070 horses sold and 56 seven-figure yearlings — the highest-grossing Thoroughbred auction ever, led by a $3.3M Gun Runner colt.
Brown-Forman eliminated 12% of its 5,400 global workforce (~650 jobs), closed its Louisville Cooperage (200+ jobs), and entered merger discussions with Pernod Ricard (March 2026 per CNBC) — the most significant strategic consolidation signal in U.S. bourbon history.
Tax & Deal Structure in Kentucky
Kentucky presents a seller-friendly M&A tax environment driven by a flat, declining individual income tax rate (4.0% in 2025, 3.5% in 2026) and full conformity to IRC §1202 QSBS. The state layers a mandatory Limited Liability Entity Tax (LLET) on top of the 5% corporate income tax, and uniquely retains an inheritance tax on non-lineal beneficiaries — a defining planning issue for multi-generational families. Kentucky's 6% statewide sales tax (no local add-ons, lower complexity than most peers) and KEDFA incentive stack (KBI, KEIA, KAITC) create both friction and opportunity. The irrevocable Form 740-PTET election is the single highest-ROI tax decision in a Kentucky exit year.
Individual Income Tax & PTET Election
FavorableKentucky imposes a flat 4.0% individual income tax in 2025, dropping to 3.5% effective January 1, 2026 under HB 1 (signed Feb. 2025). Capital gains are taxed as ordinary income at the flat rate — no preferential LTCG rate. The PTE election (Form 740-PTET, annually elected, irrevocable once made, SALT-cap workaround) allows pass-through owners to pay Kentucky tax at the entity level and receive a refundable credit; on a $80M–$100M gain, the federal SALT deduction benefit alone exceeds $1M at the 2025 rate.
QSBS IRC §1202 Full Conformity
FavorableKentucky's starting point for individual taxable income is federal AGI under KRS 141.019, meaning the federal §1202 QSBS exclusion (100% on qualifying C-corp stock held >5 years, up to $15M or 10x basis post-OBBBA July 2025) flows through automatically. Kentucky imposes no add-back for §1202 gains, making it a favorable domicile for founders of properly structured C-corps in bourbon-adjacent tech, equine health services, or Lexington SaaS targets.
Kentucky Inheritance Tax (KRS Chapter 140)
UnfavorableKentucky is one of only five states with an inheritance tax (no estate tax since 2005). Class A beneficiaries (spouse, parents, children, stepchildren, grandchildren, siblings) are fully exempt. Class B (nieces, nephews, aunts, uncles, children-in-law): $1,000 exemption, graduated 4%–16%. Class C (cousins, unrelated, non-exempt entities): $500 exemption, graduated 6%–16%. Form 92A200 due within 18 months; 5% discount if paid within 9 months; 10-year installments available for tax >$5,000. Multi-generational distillery, equine farm, and manufacturing families must channel ownership to Class A beneficiaries before sale.
Sales/Use Tax & Successor Liability (KRS 139.670)
NeutralKentucky imposes a 6% statewide sales and use tax (no local add-ons — lower combined rate than most Southeastern peers). In asset deals, tangible personal property (equipment, vehicles, inventory) is generally taxable; goodwill and IP are exempt. Successor liability applies under KRS 139.670 and 139.680: a buyer in an asset deal is personally liable for the seller's unpaid sales/use tax absent a KDOR tax clearance letter. A contractual indemnity does not relieve the statutory successor — escrow pending clearance is standard.
Limited Liability Entity Tax (LLET)
NeutralEvery limited-liability entity doing business in Kentucky owes the LLET under KRS 141.0401 — the lesser of $0.095 per $100 of Kentucky gross receipts or $0.75 per $100 of gross profits, subject to a $175 minimum. The LLET is never creditable against the 5% corporate income tax, functioning as a minimum alternate tax. For LMM businesses with healthy margins, gross-receipts-based LLET typically exceeds the $175 floor; for asset-light businesses, gross-profits-based LLET applies. LLET must be modeled in every Kentucky QoE normalization.
KEIA, KBI & KAITC Incentive Stack
FavorableKentucky's M&A-relevant incentive stack: KEIA (Kentucky Enterprise Initiative Act) refunds 100% of sales/use tax on qualifying building materials and equipment; KBI (Kentucky Business Investment) provides income tax credits and wage assessments on new job creation; KAITC (Kentucky Angel Investment Tax Credit) provides 40%/50% (enhanced county) of qualifying investments, capped at $200,000 per investor annually with a 15-year carryforward. All require advance KEDFA approval for transferability and post-closing compliance monitoring. Sellers who fail to inventory and document credits risk forfeiting 2–10% of EV.
Representative Transaction
Illustrative model only. Not representative of a current or past Ad Astra Equity client engagement. Details modified to protect client confidentiality. Ranges are representative.
The Business
Family-owned Kentucky Straight Bourbon Distiller-Producer, Bardstown/Louisville, KY
Key Metrics
Revenue
$28M-$42MEBITDA
$6.5M-$11MMargin
23-27%Aging Barrel Inventory
55,000-85,000 barrels at $400-$550/barrelThe Challenge
Key-person risk centered on the founding family's master distiller (third generation) whose proprietary mashbill and rickhouse rotation represented much of the brand's premium positioning. Kentucky-specific regulatory complexity included maintaining TTB federal DSP and Basic Permit continuity through change-of-proprietorship, transferring Kentucky ABC distiller and rectifier licenses (60-day review; mandatory 30-day newspaper publication under KRS 243.360), managing KDEP wastewater/stillage permits, preserving aging-inventory property tax treatment under the bourbon barrel tax phase-out (HB 5, 2023) without triggering reassessment, and navigating the family's inheritance tax exposure on Class B beneficiaries holding minority interests.
The Process
- 1Pre-market (90 days): 3-year QoE normalized owner comp ($850K–$1.2M addback); barrel-by-barrel inventory audit across 6 rickhouses reconciled to TTB monthly reports; KDOR LLET and sales/use tax voluntary compliance review identified $150K–$400K of historical exposure resolved pre-market; Form 740-PTET election strategy modeled for transaction year.
- 2Marketing (3-4 months): Confidential CIM distributed to 18–25 strategic and financial buyers including top-8 global spirits conglomerates, 4–6 bourbon-focused PE platforms, and 2–3 family offices; 10–14 NDAs executed; foreign-buyer CFIUS analysis completed at teaser stage.
- 3LOI/Diligence (45-60 days exclusive): LOI signed at the high end of the 11x–15x IOI range; legal, tax, environmental, and TTB/ABC diligence; KDOR sales/use tax clearance submitted at signing with 75-day escrow; inheritance tax planning executed for Class B minority holders; Form 740-PTET election made for stub period.
- 4Close (60-90 days): Kentucky ABC license transfer filed (transitional KRS 243.045 license covered the bridge period); TTB DSP change-of-proprietorship notification submitted; KDEP permits assigned; KEDFA written consent to KBI/KEIA credit assignment obtained; barrel inventory separately valued at $425–$575/barrel independent of EBITDA multiple.
Deal Outcome
Enterprise Value
12.0x-15.5x adjusted EBITDA
Premium vs. Market
20-30% above craft-distiller comparable transactions
Time to Close
~9-11 months
Seller Rollover
75-85% cash at close, 10-15% rollover equity, 5-10% earnout tied to brand-level case depletions over 24 months; master distiller retained under 3-year consulting + royalty agreement
Key Lessons
- Barrel inventory is a separate valuation conversation — buyers underwrite aged stocks at cost-plus or per-barrel market rates independent of EBITDA multiple; on 55,000–85,000 barrels at $400–$550/barrel, this added $25M–$45M to enterprise value above the EBITDA-multiple headline.
- Kentucky PTET election timing is a seven-figure decision — electing Form 740-PTET for the stub period converts Kentucky's 4.0%/3.5% tax into an entity-level federal deduction; on $80M–$100M of gain, federal SALT benefit alone exceeds $1M–$1.5M.
- Kentucky ABC license transfers and TTB DSP change-of-proprietorship control the closing calendar — build a 60–90 day regulatory bridge with pre-cleared transitional licenses (KRS 243.045); plan inheritance tax and family-trust restructurings well in advance because KY's Class B/C rates (4%–16%) apply to any non-lineal shareholders receiving proceeds.
- Pre-market resolution of KDOR LLET and sales/use tax exposure through voluntary compliance preserved deal economics and prevented buyer price-chips during diligence — the $150K–$400K in historical exposure identified would have traded at 2x–5x that cost in purchase price adjustment had it surfaced during confirmatory diligence.
Frequently Asked Questions
Common questions about selling a business in Kentucky.
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