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When a Client has been Around the Block: Failed Offers in Compromise, Bad Bankruptcies, and Previously Poor Service

Thursday, September 10, 2026 · 2:00 p.m.  |  Eastern Time (US & Canada) (GMT -4:00)

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Presenters
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Alexander Robinson
Alexander enjoys solving tax problems for clients. He has over two years of tax resolution experience. He earned his LLM in Taxation from the Northwestern Pritzker College of Law with a certificate in international taxation. He also, earned his JD from the Loyola New Orleans College of Law with certificates in tax law, international law & the civil law. He is a member of the Chicago Bar Association, Illinois State Bar Association and the District of Columbia Bar Association. Alexander also enjoys fishing, hiking and reading about American history.
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Rebecca Sheppard
Rebecca Sheppard is a Partner at Frost Law with extensive experience representing clients before the IRS and state taxing authorities. She advises on audits, appeals, and tax litigation, focusing on employment tax and the Employee Retention Credit. Rebecca is known for her practical, innovative approach to controversy work and her ability to translate complex tax issues into actionable guidance for practitioners. She regularly speaks on tax procedure and controversy topics to professional audiences. She is a member of the Maryland State Bar Association’s Taxation Section Council.
About
Program Field of Study: Taxes, Federal Tax Related Matters
Program Level: Basic
Credits: 1 CPE | 1 CE
Advanced Preparation: None
Prerequisite: None
IRS Program Number: JWRXB-T-00026-26-O

Unfortunately, not all tax resolution plans—whether an offer in compromise, a bankruptcy petition filed too soon, or simply an installment agreement that was unaffordable—go as planned or achieve good results for clients. When dealing with a client who has been a victim of an offer mill, an ill-advised bankruptcy, or an installment agreement that failed to adequately meet the taxpayer’s cash flow reality, it is important to review the situation with the client, take a fresh perspective, and develop a new plan that will work.
Agenda
  • Develop skills on how to analyze a taxpayer's current financial situation to determine the feasibility of a new resolution plan
  • Review how to discuss new compliance habits with clients to help prevent future noncompliance
  • Evaluate available resolution options to identify the best fit for clients' circumstances
  • Assess the root causes of a failed offer in compromise, premature bankruptcy filing, or unaffordable installment agreement
  • Identify warning signs of offer mill practices and other red flags that may have contributed to a client's prior unsuccessful resolution
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