Captive Insurance Practice



Jay Adkisson's practice includes the litigation of controversies involving captive insurance companies. Jay is a past Chair of the American Bar Association's Committee on Captive Insurance (2011-2014), and is the author of the widely-selling Adkisson's Captive Insurance Companies (2006). From 1998 to 2003, Jay was one of the owners of a successful captive insurance consulting firm, and a licensed captive insurance management firm based in the British Virgin Islands. Jay has also litigated controversies involving captive insurance structures, and served as an expert witness in cases implicating captive insurance issues.

Jay has also been involved in the structuring and formation of over 100 captive insurance companies, and also provides second-opinion review of such structures, and ancillary issues such as insurance policies, risk pools, claims procedures, etc.


Adkisson's Captive Insurance Companies



Adkisson's Captive Insurance Companies available at Amazon.


Articles On Captive Insurance



2024.09.19 ... Indian Tribe-Based Microcaptive Flops In Royalty Management

2024.04.13 ... Captive Manager Avoids 6700 Penalties After Jury Trial

2024.04.07 ... Florida Looking To Collect 5.3% Tax Against Out-Of-State Captive Insurers

2024.04.06 ... Another Taxpayer Microcaptive Blowout Loss In Patel

2024.02.12 ... Prolific Microcaptive Promoter Strauss Pleads Guilty

2024.02.10 ... Sixth IRS Victory Against Microcaptives In Swift

2024.01.11 ... IRS Wins Fifth Microcaptive Case In Keating

2023.10.28 ... Abusive Captive Tax Shelters Continue To Be Sold Despite IRS Efforts

2023.05.22 ... Third Circuit Denies Appeal Of The Delaware Department Of Insurance In Tax Shelter Captive Summons Case

2023.04.17 ... A Deeper Dive Into The Two Tests For Microcaptive Tax Shelters Under Treasury’s Proposed Regulations

2023.04.11 ... U.S. Treasury Department Issues Proposed Regulations To Finally Eviscerate Microcaptive Tax Shelters

2023.03.07 ... The U.S. Tax Court Rejects 501(c)(15) Status For Commonwealth Underwriting & Annuity Services, Inc.

2023.02.20 ... Captive Manager Arsenal Insurance Files For Bankruptcy Protection After Allegations Of Fraud By Its Former Owner

2023.02.10 ... Ambassador Captive And Brandon White Fiasco Highlights Need For Better Captive Manager Oversight

2023.01.19 ... Attorney Stewart Feldman And Captive Manager Capstone Hit With Almost $90 Million Judgment By Their Clients

2023.01.17 ... Pinnacle Actuarial Summoned By IRS To Produce Documents In Promoter Examination Of Oxford Insurance

2022.09.30 ... IRS Drops Appeal Regarding Notice 2016-66’s Invalidation For Microcaptives

2022.08.08 ... Eleventh Circuit Rules For IRS In Dispute Over Privileged Documents Relating To Moore Ingram’s Microcaptives

2022.06.07 ... IRS Dirty Dozen List Includes Abusive Puerto Rico Captive Insurance Transactions

2022.06.06 ... IRS Wins Ruling On Reconsideration In CIC Services Case Which Cuts Practical Effect Of The Ruling To Almost Nothing

2022.05.16 ... Tenth Circuit Issues Landmark Microcaptive Insurance Company Opinion In Reserve Mechanical

2022.03.28 ... IRS Notice 2016-66 On Microcaptives Vacated By U.S. District Court On Procedural Grounds In CIC Services Case

2022.01.31 ... IRS Attorney Hiring Binge Spells More Trouble For Microcaptives And Syndicated Conservation Easements

2021.07.23 ... Delaware Department Of Insurance Loses IRS Summons Fight For Artex And Tribeca Captives But Can Appeal

2021.05.20 ... U.S. Supreme Court Rules On Anti-Injunction Act In Microcaptive Context

2021.04.26 ... The IRS Warns Again On Microcaptives And Announces A New Office Of Promoter Investigations

2021.03.22 ... The U.S. Tax Court Drives A Stake Into The Heart Of Microcaptives In Caylor Land

2020.12.31 ... U.S. District Judge Denies Blanket Assertion Of Attorney-Client Privilege In Moore Ingram Microcaptive Promoter Audit Case

2020.10.22 ... IRS Announces A Second Settlement Initiative For Abusive Microcaptive Tax Shelters But With Much Stricter

2020.10.02 ... IRS Warns Microcaptive Shelter Penalties To Get Much Worse, Taking On The Puerto Rico Deal And Other Next-Generative Captive Shelters

2020.09.23 ... U.S. Tax Court Affirms Most Penalties In Patel Microcaptive Shelter Case But Kicks Out Some For IRS Procedural Errors

2020.09.12 ... Microcaptive Manager Artex And Related Professionals Dodge The Class Action Bullet In Shivkov

2020.09.10 ... GAO Report To Grassley At Senate Finance Slams Offshore Microcaptive And Variable Life Insurance Transactions

2020.08.24 ... Buyers Of Jade Risk Get Taken To Woodshed In Litigation Arising From Merger Of Captive Insurance Managers

2020.08.08 ... IRS Sends Second Wave Of Soft Letter Warnings To Certain Captive Owners For Abusive Microcaptive Transactions

2020.07.27 ... Microcaptive Tax Shelter Promoter Investigation Of Moore Ingram Law Firm Leads To Attorney-Client Privilege Issues With Client Documents

2020.07.22 ... U.S. Tax Court Approves Penalties For Microcaptive Transaction In Oropeza

2020.06.24 ... The U.S. Department Of Justice Files Suit To Enforce An IRS Summons Against The Delaware Department Of Insurance For Artex Transactions

2020.05.19 ... Coronavirus Pandemic Threatens Run On Business Interruption Policies Sold By Captive Insurance Risk Pools

2020.04.17 ... Coronavirus Pandemic Will Not Slow Down IRS’s Pursuit Of Microcaptive And Syndicated Conservation Easement Transactions Says LB & I Memo

2020.02.04 ...The IRS Strikes A Rich Seam Of Tax And Penalty Gold In Risk-Pooled 831(b) Captives And Is Sending In More Miners

2019.12.31 ... The Next Generation Captive Insurance Tax Shelter Explained

2019.12.05 ... Bitter Coffee: Starbucks Squabbles With The Washington Insurance Commissioner Over $633 Million Paid To Its Captive Insurance Company

2019.11.17 ... IRS Suggests Criminal Referrals To Be Made In Abusive 831(b) Captive Tax Shelter Cases

2019.09.28 ... Johnson & Johnson Wins Appeal On $60 Million Tax Case To New Jersey For Captive Insurance Company

2019.09.26 ... Understanding The IRS Settlement Initiative Offer For Targeted 831(b) Captive Insurance Companies

2019.09.16 ... IRS Announces Global Settlement Of Abusive 831(b) Captive Insurance Tax Shelters

2019.08.08 ... Artex Defeats Attempt To Form Class Action And Forces Individual Arbitration Of Captive Disputes

2019.07.04 ... Second Class Action Against A Risk-Pooled 831(b) Captive Promoter Roils Sector

2019.05.28 ... New York Denies Stewart's Shops Deduction For Premiums Paid To Its Captive Insurance Company

2019.05.23 ... Sixth Circuit Also Gives CIC Services Thumbs-Down On IRS Notice 2016-66 Challenge

2019.04.23 ... Third US Tax Court Opinion Denies Deductions For Risk-Pooled 831(b) Captive Arrangement In Syzygy

2019.03.29 ... Macy’s Captive Insurance Company Faces Potential $23.8 Million In Maryland Corporate Tax Liability

2018.12.20 ... Class Action Targets Arthur J. Gallagher & Co. Over Captive Insurance Tax Shelter

2018.09.05 ... Whistleblower Yanks Back Rug To Expose Alleged Dirt Of Moody's Captive Insurance Company

2018.07.28 ... Johnson & Johnson Loses $60 Million Case To New Jersey For Captive Insurance Company

2018.06.25 ... Analysis Of The IRS's Big Win Against Risk-Pooled Small Captives In Reserve Mechanical

2018.06.19 ... Capstone's PoolRe Fails To Provide Risk Distribution In Reserve Mechanical Captive Insurance Case

2018.05.27 ... Washington State Goes After Microsoft's Captive For Unpaid Premium Taxes And Unauthorized Insurance

2018.01.27 ... Beware The Puerto Rico Captive Insurance Tax Shelter

2017.11.17 ... Avrahamis Motion For Reconsideration Rolls Snake-Eyes In U.S. Tax Court

2017.11.04 ... Court Pours Out Lawsuit By CIC Services, LLC, And Ryan, LLC, To Stop Notice 2016-66

2017.10.19 ... Foster & Dunhill Saga Ends With Convictions And Donaldson Claiming To Be Too Fat To Jail

2017.10.11 ... Risk-Pooled 831(b) Captive Insurance Companies And Bad Practices Take A Beating In Avrahami

2017.09.30 ... Avrahamis Captive Manager Apparently Calling It Quits After Decision

017.08.21 ... IRS Notches Big Tax Court Win On 831(b) Captive Insurance In Avrahami Decision

2017.07.19 ... Donaldson And Crithfield Found Guilty In Foster Dunhill Offshore Insurance Tax Evasion Case

2017.06.25 ... Beware The Insane New Offshore Insurance Company Deals Sold By Some 831(b) Captive Managers

2017.04.23 ... Last Gasp Attempt To Stop Notice 2016-66 Fails, May 1 Filing Deadline Approaches Quickly

2016.12.31 ... IRS Extends Deadline For Compliance With Notice 2016-66 For 831(b) Captives To May 1, 2017

2016.11.16 ... A Detailed Analysis of IRS Notice 2016-66 re 831(b) Captives

2016.11.13 ... Pretrial Memoranda Filed In Wilson 831(b) Captive Case Display IRS Attacks and Taxpayer Responses

2016.11.08 ... IRS Notice 2016-66 Regarding 831(b) Captive Insurance Companies Interpreted In Common English

2016.11.01 ... IRS Categorizes Certain 831(b) Captive Insurance Companies As A "Transaction Of Interest"

2016.11.16 ... A Detailed Analysis of IRS Notice 2016-66 re 831(b) Captives

2016.11.13 ... Pretrial Memoranda Filed In Wilson 831(b) Captive Case Display IRS Attacks and Taxpayer Responses

2016.11.08 ... IRS Notice 2016-66 Regarding 831(b) Captive Insurance Companies Interpreted In Common English

2016.09.29 ... Not All Captive Insurance Risk Pools Are Created Equally

2016.03.03 … Happy 75th Birthday to Helvering v. LeGierse

2015.12.19 ... Congress Makes 831(b) Captives Much Better And Deals With (Some) Abuses In 2015 Appropriations Bill

2015.12.08 ... 2015 Extender Bill May Throw Out 831(b) Captive Baby With The Bathwater

2015.11.29 ... The Sum Of All Fears About IRC 831(b) Tax Shelter Captives In Avrahami

2015.09.27 ... Residual Value Insurance Scores Big Win In U.S. Tax Court

2015.08.12 ... Donaldson And Crithfield Enter Guilty Pleas In Foster Dunhill Tax Fraud Case

2015.06.11 … Treasury To Study Possible Abuses Of Small Captive Insurance Companies

2014.11.01 ... Securitas Secures Big Win For Captive Insurance In U.S. Tax Court

2014.09.18 ... IRS Launches Promoter Audits Of Captive Managers Suspected Of Abusive Practices

2014.04.20 ... Life Insurance and the 831(b) Captive Insurance Company – Wait For The Test Case Before Signing Up

2014.03.27 ... The IRS Discloses The 953(d) Trapdoor For Offshore Captives

2014.03.17 ... IRS Noose Starting To Tighten On Sham Risk Pools

2014.02.21 ... Rent-A-Center Creates A Captive Insurance Legacy In Tax Court

2013.11.16 ... Cell Captives And The Recycling Of Capital

2013.09.28 ... Manager Complaints Bubble To Surface Regarding Delaware Captive Insurance Companies

2013.09.21 ... IRS Filling The Pipeline With Captive Insurance Cases And Focusing On Dubious Practices

2013.08.10 ... Ten Favorite Things About Captive Insurance Companies

2013.07.28 ... Tax Shelters, Nebraska Hurricanes And Other Captive Insurance Mistakes

2013.06.23 ... Foster and Dunhill Scheme Ends In Denial Of Deductions And Indictments For Bogus Insurance Tax Shelter

2013.06.09 ... Texas Adopts Captive Insurance Legislation But Beware

2012.08.31 ... Broughton -- Rented Assets And Bogus Offshore Insurance Companies

2012.02.09 ... Sperl : Offshore Reinsurance Scheme And Other Tax Evasion Nets Accountant 36 Months

2011.09.24 ... 'Tis The Season For Tax Shelters, Fa La La La La And Grab Your Wallet


Speaking Appearances On Captive Insurance



2019.01.24 ... LISI Webinar ... Jay Adkisson presented the State of the Union re 831(b) Captive Insurance Companies for Leimberg Information Systems.

2016.12.1 ... Columbus, OH ... Jay Adkisson presented "Captive Insurance Companies" at the Fourth Annual Ohio Asset Protection Institute.

2017.09.20 ... Phoenix ... Jay Adkisson presented "Captive Insurance Update" to the Arizona Captive Insurance Companies Association.

2015.12.18 ... ABA Webinar ... Panelist for the webinar "Congressional Changes to Tax Code Section 831(b)", sponsored by the ABA Committee on Captive Insurance.

2015.11.18 ... Phoenix, AZ ... Presented "Captive Insurance Hot Issues" to the Arizona Captive Insurance Companies Association.

2015.9.18 ... Chicago ... A panelist for "Nuts & Bolts of Captive Insurance Taxation" at the Joint Tax/Real Property, Trusts & Estates Sections meeting of the American Bar Association.

2015.4.30 ... American Bar Association CLE Webinar ... Jay Adkisson spoke on the panel "Captive Insurance Best Practices and the Defense of IRS Attacks"

2015.4.16 ... San Francisco ... Jay Adkisson moderated the panel "Protected Cell Captive Insurance Companies" and spoke on the panel "Limited Liability Entities ... Current Bankruptcy Issues" at the Spring Symposium of the American Bar Association's Business Law Section

2014.5.14 ... A panelist for the presentation "Why Clients Across the Spectrum are Increasingly Using Captive Insurance Risk Management" presented by the American Bar Association Section on Real Property, Trusts & Estates

2014.5.6 ... Miami ... Presented "Offshore Insurance Frauds, Schemes and Scams" at the OffshoreAlert Conference

2014.4.10 ... Los Angeles ... Jay Adkisson moderated the panel presenting "Captive Insurance ... Tax & Regulatory Update" at the Spring Meeting of the American Bar Association's Committee on Captive Insurance Companies of the Business Law Section

2012.3.12 ... Scottsdale, Arizona ... Presented "Avoiding Disasters With Captive Insurance Planning" at the 2012 Annual Conference of the Captive Insurance Companies Association

2011.9.29 ... Salt Lake City ... Panel presentation "Does Your 831(b) Captive Quack" at the Western Region Captive Insurance Conference ("Western Captive Round...Up")

2011.9.18 ... San Diego ... Presented "Captive Insurance: Business Owner Risk Management and Wealth Accumulation" at the Financial Planning Association's FPA Experience 2011

2011.8.7 ... Toronto ... Moderated the panel "Captive Insurance Companies: Introduction and Update" sponsored by the American Bar Association's Committee on Captive Insurance at the Business Law Section's Annual Meeting

2009.9.23 ... Portland, OR ... Keynote speaker at the First Annual Oregon Captive Conference

2009.5.5 ... Washington DC ... Presented "Captive Insurance Companies" at the American Association of Life Underwriters

2009.2.17 ... Houston … "Captive Insurance" at the Houston Chapter of the Society of Financial Services Professionals

2008.10.17 ... Des Moines, IA ... Presented "Captive Insurance Companies" at the Midwest Tax Conference.

2008.9.19 ... Park City, UT ... Expert panelist at the Annual Meeting of the Utah Captive Association

2008.4.4 ... San Diego ... Presented "Captive Insurance Companies" at the BGA Sales Summit 2008 of the Underwriting Services of America

2007.10.18 ... San Diego, CA ... Moderated the panel "Understanding Captive Insurance Companies" and the workshop "Captive Insurance for Wealth Transfer and Preservation" at the 27th Annual Southern California Tax & Estate Planning Forum

2007.7.25 ... San Diego, CA ... Presented "Captive Insurance Strategies" at the Best Practices of America 2007 Symposium

2007.4.24 ... Miami, FL ... Presented "Captive Insurance Companies" at the 5th Annual OffshoreAlert Financial Due Diligence Conference