Rubenstein rachael web

Rachael E. Rubenstein


San Antonio

2301 Broadway Street
San Antonio, TX 78215
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Fax: +12102582714
J.D., cum laude, St. Mary's University School of Law, San Antonio, Texas, 2010, St. Mary’s Law Journal; The John M. Harlan Society
B.A., magna cum laude, Texas State University-San Marcos, San Marcos, Texas, 2006, Graduate of Mitte Honors Program
State Bar Licenses
Court Admissions
U.S. Court of Appeals, 5th Circuit
U.S. Tax Court
U.S. Court of Federal Claims
U.S. District Ct., W.D. of Texas
U.S. District Ct., S.D. of Texas
U.S. District Ct., E.D. of Texas

Rachael E. Rubenstein


Rachael E. Rubenstein helps clients to resolve tax-related problems and to comply with regulatory obligations. She has extensive experience in: 

Federal Tax Controversy

  • Tax Litigation. Represent clients in litigation against the IRS in the United States Tax Court and in other federal courts.
  • Penalties. Advocate for clients to reduce or eliminate penalties imposed.
  • Appeals. Negotiate for fair resolution of controversies before IRS Appeals without the need for litigation.
  • Examinations. Advocate for clients in audits involving wide-range of issues, including: business expense deductions, unreported income, credits, employee classification, valuations, imposition of penalties, and fraud.
  • Collections. Defend clients with tax debts facing levies, liens, garnishments and other IRS enforcement activities. Negotiate collection alternatives with IRS such as Installment Agreements, Offers In Compromise, and Noncollectible Status.
  • Trust Fund Recovery Penalty Disputes. Defend clients facing personal liability for failure of business to pay payroll taxes.
  • Criminal Tax. Defend clients in criminal tax investigations, prosecutions, and restitution enforcement proceedings.
  • Third Party Liability. Represent clients facing IRS alter ego, nominee, and transferee collection enforcement activities.

Trusts & Estates

  • Counsel fiduciaries regarding income tax obligations and IRS compliance matters. 
  • Represent trusts and estates in disputes involving income, estate, and gift tax issues.


  • Advise U.S. citizen and resident clients on myriad of reporting obligations concerning foreign income, foreign financial accounts, and other offshore assets, including application of Bank Secrecy Act (BSA) and Foreign Account Tax Compliance Act (FATCA).
  • Assist nonresident clients with U.S. tax obligations and related compliance issues concerning investments, business activities, inheritance, and immigration. 
  • Help bring into compliance clients worldwide who have FBAR failures, whether accidental or intentional.
  • Represent clients in administrative investigations and litigation involving significant penalties related to foreign financial accounts, foreign companies, and other offshore assets.

Tax Planning

  • Develop and implement strategies for businesses to maximize tax savings.
  • Advise business clients on application of new federal tax laws, including the Families First Coronavirus Response Act (FFCRA) and the Coronavirus Aid, Relief, and Economic Security (CARES) Act.
  • Educate individuals and businesses on tax compliance, IRS procedural matters, and best practices to avoid controversies.

Tax Issues in Divorce, Litigation and Settlement

  • Advise and assist clients and other professionals regarding tax issues in divorce, litigation, and settlement.

Tax Professionals

  • Represent tax professionals in IRS controversies and state disciplinary proceedings.

Employee Benefits

  • Counsel clients regarding Affordable Care Act (ACA) planning, compliance, and penalties.
  • Represent clients in benefit plan audits and voluntary compliance programs for plan errors.


Notable Published Opinions

  • United States v. Bittner, No. 4:19-CV-415, 2020 WL 3498082 (E.D. Tex. 2020).
    United States District Court granted a partial summary judgment to the taxpayer holding that governing statute capped non-willful FBAR penalties to $10,000 per FBAR form (each year), rather than per account. As a result, the court struck down largest non-willful penalties ever assessed against a taxpayer related to foreign bank accounts. Case of first impression in the Fifth Circuit.
  • Nelson v. Commissioner, T.C. Memo. 2020-81 (2020).
    United States Tax Court decision following trial on gift valuation of limited partnership interests resulted in overall 70% victory for the taxpayer, compared to the IRS's asserted values. Tiered discounts for lack of control and lack of marketability permitted.
  • Kaplan v. United States, 115 Fed. Cl. 491 (2014).
    The Court of Federal Claims held it had jurisdiction to prevent “manifest injustice” in a refund suit involving assessed trust fund recovery penalties against an investor for failure of the business to pay employment taxes. Identified as one of the most significant tax cases of the year in the National Taxpayer Advocate's 2014 Annual Report to Congress.

Select Presentations

  • Legal & Tax Issues Related to Cannabis/CBD, Texas CPA Tax Institute (November 2019).
  • IRS Collection Enforcement Against Third Parties – Alter Egos, Nominees, and Transferees, Texas Society of Enrolled Agents Jalapeno Chapter (July 2019).
  • Section 199A: Understanding and Maximizing the 20% Pass-through Deduction, San Antonio CPA Society (June 2019). 
  • IRS Appeals and Alternative Dispute Resolution: Navigating the IRS Appeals Process, Lorman Webinar (May 2019). 
  • 2018 Hot Topics in Federal Controversy, Clark Hill Strasburger Annual Symposium (November 2018). 
  • Taxation of Corporations & Partnerships CLE, South Carolina Society of Accountants (October 2018). 
  • What to do When the IRS Comes Calling: Dealing with IRS Controversies, In-House Counsel Webinar Series Event (July 2018).
  • Tax Cuts and Jobs Act of 2017.  Be Prepared!, San Antonio CPA Society (January 2018).
  • Hot Topics in Tax Controversy, Strasburger's Tax Symposium (November 2017).
  • Handling Non-Filer Situations, San Antonio CPA Society (September 2017).
  • Tax Topics and Choice of Entity Decisions for Solo/Small Law Firms, Austin Bar, Solo/Small Firm Section CLE (March 2017).
  • Understanding Small Business Taxes, San Antonio LiftFund (January 2017).
  • Tax Issues in Divorce, Austin Chapter CPA Tax Conference (November 2016).
  • Community Property & Federal Tax Issues, San Antonio Society of Enrolled Agents (October 2016).
  • Tax Advice for Sole Proprietors and Single Member LLCs, San Antonio LiftFund (April 2016).
  • Individual Tax Update, PATH Act, and Changes to TEFRA Partnership Audit Rules, ADKF (January 2016).
Recipient of Award for Outstanding Service and Leadership as Pro Bono Co-Chair for Tax Section of the State Bar of Texas (2019)
Recipient of Strasburger's Bob Thomas Award for Community Service (2018)
Recipient of Strasburger's Keith Drummond New Associate of the Year Award (2017)
Recipient of Francisco Leos Award for Excellence in Clinical Studies (2009)
Recipient of San Antonio Bar Auxiliary Foundation Olive Trueheart Scholarship (2008)
Recipient of Joseph R. Steele Memorial Scholarship (2008)
Tax Section of the State Bar of Texas, Pro Bono Co-Chair & Council Member
Tax Section of the State Bar of Texas, Pro Bono Co-Chair & Council Member
VITA Adopt-A-Base
Tax Court Pro Bono Calendar Call Program
State Bar of Texas Pro Bono College
Tax Section of the American Bar Association
Temple Beth-El