Gray Proctor is a board-certified appellate specialist and seasoned federal litigator whose practice sits at the intersection of appellate advocacy, tax controversy, and administrative law. As one of fewer than one percent of active Florida Bar members to hold board certification in appellate practice, he brings a rare combination of procedural rigor and substantive depth to every case he handles.
Andy Steigleder is a Partner at Kostelanetz LLP whose practice is built on a defining conviction: all significant tax matters are valuation matters. With a multidisciplinary background spanning tax law, accounting, finance, and securities, he brings a uniquely cohesive perspective to tax planning, compliance, controversy, and litigation.
What Will You Learn
Attorneys will learn the statutory framework of Section 7508A, key court decisions invalidating limiting regulations, and avenues for taxpayer relief during COVID-19.
What Will You Gain
Attorneys will gain the ability to raise claims administratively, challenge collections, and calculate interest and penalties to be disregarded under Section 7508A.
Key topics to be discussed:
This course is co-sponsored with myLawCLE.
Date / Time: May 15, 2026
Closed-captioning available
Gray Proctor, Counsel | Kostelanetz LLP
Gray Proctor is a board-certified appellate specialist and seasoned federal litigator whose practice sits at the intersection of appellate advocacy, tax controversy, and administrative law. As one of fewer than one percent of active Florida Bar members to hold board certification in appellate practice, he brings a rare combination of procedural rigor and substantive depth to every case he handles. His published scholarship on the constitutional implications of SEC v. Jarkesy for tax penalty procedure has been cited by courts and practitioners as a leading analysis of the administrative law shifts reshaping federal regulatory enforcement.
Gray earned his J.D. from Vanderbilt University Law School, where he was named to the Dean’s List and received the Book Award for Criminal Procedure. He also holds a B.S. from the University of Texas at Dallas and an M.A. from the University of New England. He is admitted to practice before the United States Supreme Court, the United States Tax Court, the First through Sixth and Eleventh Circuit Courts of Appeals, multiple federal district courts across Florida and Georgia, and the state bars of Florida and Georgia. He has been board certified in appellate practice by the Florida Bar since 2021.
Gray has earned distinction at every stage of his career. He completed three prestigious federal clerkships — on the U.S. Court of Appeals for the Fourth Circuit, the U.S. District Court for the Eastern District of Virginia, and the U.S. District Court for the Southern District of Texas — a breadth of judicial experience that sharpened his appellate instincts and procedural command. He is AV Preeminent rated by Martindale-Hubbell, the highest peer-review rating available, and has been recognized by Florida Trend magazine as a Florida Legal Elite in Appellate Practice. His amicus work on behalf of the Center for Taxpayer Rights — spanning briefing before the U.S. Tax Court, the Eleventh Circuit, and the Supreme Court — has positioned him as a thought leader in the constitutional questions now transforming federal tax enforcement.
Gray is an active voice in the tax controversy and appellate communities. He has spoken on the ongoing impact of Jarkesy on tax penalty adjudication and has presented at forums including the IFA North America Trilateral Current Developments Webinar. He is a published author on topics including Eighth Amendment excessive-fines challenges to tax promoter penalties and due process limitations on refund jurisdiction. Beyond his private practice, Gray demonstrates a strong commitment to access to justice. He accepts court-appointed representations under the Criminal Justice Act in the Sixth and Eleventh Circuits, advocating for indigent defendants in direct criminal appeals. He has also represented clients in death row clemency proceedings and contributed to post-conviction relief efforts, including the successful reversal of a high-profile Tennessee murder conviction.
Gray’s appellate practice encompasses the full lifecycle of federal tax controversies — from preserving constitutional and statutory challenges at the U.S. Tax Court level, to developing appellate strategy as cases advance to the circuit courts, to briefing and oral advocacy before the circuits and the Supreme Court. He has played a central role in coordinating Jarkesy-based Seventh Amendment and Article III challenges across multiple Tax Court proceedings and has provided briefing support in large-scale consolidated trials involving conservation easement partnerships facing substantial federal tax and penalty exposure.He also serves as appellate co-counsel to trial teams in matters beyond tax, particularly cases involving federal agency action and APA procedure, where his background adds a dimension of expertise that few appellate generalists can match. His broader appellate practice includes commercial litigation, insurance coverage disputes, and criminal appeals in both state and federal courts.
Andy Steigleder, Partner | Kostelanetz LLP
Andy Steigleder is a Partner at Kostelanetz LLP whose practice is built on a defining conviction: all significant tax matters are valuation matters. With a multidisciplinary background spanning tax law, accounting, finance, and securities, he brings a uniquely cohesive perspective to tax planning, compliance, controversy, and litigation. From IRS audits and administrative appeals to high-stakes trials in the U.S. Tax Court and the federal courts, Andy helps clients across industries navigate complex tax disputes with strategic precision and an unwavering focus on protecting their financial interests.
Andy holds a J.D. from Creighton University School of Law, an LL.M. in Taxation from Northwestern University Pritzker School of Law, an M.B.A. from Creighton University School of Business, and a B.B.A. from Loyola University New Orleans. This combination of legal, tax, and business education gives him rare cross-disciplinary fluency — an advantage he brings to every engagement. He further holds Securities Industry Essentials (SIE), FINRA Series 7, and FINRA Series 63 certifications, equipping him with a working command of the financial and securities dimensions that frequently underpin complex tax controversies. Andy is admitted to practice in Illinois, the U.S. Tax Court, the U.S. Court of Federal Claims, and the Second and Seventh Circuit Courts of Appeals.
Andy has built a distinguished reputation over a career that spans two of the nation’s most prominent professional services institutions. Before joining Kostelanetz, he served as a Principal at Ernst & Young LLP, where he led the Tax Policy & Controversy practice for the U.S. Central Region from 2016 to 2019. Prior to EY, he spent 13 years as a Partner at Mayer Brown LLP within its Tax Controversy & Transfer Pricing group. His transition from Big Four leadership and AmLaw 100 partnership to a premier tax controversy boutique reflects the depth and specialization he brings to his clients. Among his most notable accomplishments, Andy successfully lobbied Congress and drafted proposed legislation that was adopted as a technical correction to IRC § 6404(g) concerning the interest suspension on underpayments of tax — a direct contribution to the development of federal tax law.
Andy is an active participant in the tax controversy community. He has spoken at the ABA Criminal Tax Fraud and Tax Controversy Conference and engages regularly with the professional and policy dimensions of tax practice. His work teaming with clients’ financial, economic, valuation, and industry experts reflects a collaborative approach that extends beyond traditional legal counsel to encompass the full strategic landscape of each matter.
Andy’s practice covers the full arc of tax controversy and planning. He regularly advises clients on audit readiness, IRS examination defense, administrative appeals, settlement structuring, and federal tax litigation. His experience spans matters involving complex financial and tax-advantaged transactions, economic substance and substance-over-form challenges, intercompany transactions and transfer pricing, and a wide range of valuation disputes. His representative matters include landmark cases litigated in the U.S. Tax Court, the Court of Federal Claims, and the federal circuit courts — including disputes involving billion-dollar like-kind exchanges, leveraged lease transactions, and substance-over-form challenges brought against major financial institutions and energy companies. He has overseen the global settlement of coordinated IRS examinations involving more than 750 former partners of a major accounting firm, in which the IRS sought over $450 million in taxes, and led a coalition-wide settlement for more than 50 high-net-worth individuals facing over $500 million in asserted taxes and penalties. Andy currently handles select, high-profile conservation easement tax controversies — one of the IRS’s highest-priority enforcement campaigns — and continues to advise multinational companies on transfer pricing planning, documentation, and dispute resolution. His client base ranges from startups and high-net-worth individuals to multinational corporations and financial institutions across the energy, transportation, technology, manufacturing, life sciences, and financial services sectors.
SESSION 1 – Understand Disregarding Periods Under Sections 7508 and 7508A | 1:00pm – 1:15pm
Explore the statutory framework of Sections 7508 and 7508A, including how these provisions suspend tax deadlines during declared disasters and their critical application during the COVID-19 emergency period.
SESSION 2 – Limits on §7508A: Treasury Failures & Reform | 1:15pm – 1:30pm
Analyze how Treasury regulations attempted to narrow Section 7508A’s mandatory relief during COVID-19, why courts invalidated those limits in Kwong and Abdo, and how subsequent congressional amendments prevent similar relief for future disasters.
SESSION 3 – Raising the Claim in Admin or CDP | 1:30pm – 1:45pm
Learn the procedural steps for filing administrative refund claims using Form 843 and raising Section 7508A relief in Collection Due Process hearings to preserve client rights before critical deadlines expire.
SESSION 4 – Calculate §7508A Relief Using AI | 1:45pm – 2:00pm
Master practical techniques for computing refundable interest and penalties across the COVID-19 postponement period, including leveraging AI tools to analyze IRS transcripts and accurately quantify client refund amounts on Form 843 claims.