This course reviews federal income US tax considerations affecting owners of and lenders to troubled businesses. We start with a discussion of rules concerning debt restructurings, and their implications to lenders and borrowers. We review considerations concerning the protection of valuable tax attributes, such as net operating loss carryovers. We then cover approaches for harvesting tax benefits for losses on entities and investments. We then describe certain hazards that can arise in capitalizing on a troubled entity. Finally, we discuss potential personal liability to management and other responsible persons for “trust fund” taxes.

The course is designed for accountants, managers, financial professionals, investors, CFOs, and other professionals who operate, invest in, or otherwise are affected by, businesses and investments in financial distress.

Learning Objectives
  • Explore and learn common approaches to debt restructurings and modifications and their tax implications.
  • Discover and understand US tax rules affecting net operating losses, restrictions on their usage, and considerations regarding loss management and planning under current tax rules.
  • Identify ways of harvesting tax benefits for losses on business assets and investments.
  • Discover and understand pitfalls that can apply in capitalizing companies that have become subject to financial distress.
  • Explore and learn about potential pitfalls concerning personal liability for withheld employment taxes by troubled entities.
Last updated/reviewed: August 9, 2023
2 Reviews (14 ratings)


Anonymous Author
Tax isn't my normal area and this was pretty involved but as long as you pay attention the info is easily learned.

Member's Profile
Lots of good information in this course. Not for beginners or those looking for a high-level overview.

Course Complexity: Foundational

Fundamental knowledge of common tax, business, and legal terms. Finance and accounting professionals with some tax background would generally have this knowledge.

Education Provider Information
Company: Illumeo, Inc., 75 East Santa Clara St., Suite 1215, San Jose, CA 95113
Contact: For more information regarding this course, including complaint and cancellation policies, please contact our offices at (408) 400- 3993 or send an e-mail to .
Instructor for this course
Course Syllabus
  Introduction to Tax Planning for Troubled Businesses and Investments4:06
  Debt Foreclosures and Restructurings10:58
  Debt Foreclosures and Other Transfers11:16
  Debt Foreclosures and Restructurings Cont'd10:38
  Protecting Tax Attributes15:08
  Protecting Tax Attributes Cont'd11:00
  Harvesting Losses11:26
  Harvesting Losses Cont'd9:23
  Capitalization Hazards5:22
  "Trust Funds" Taxes5:09
  Conclusion 4:46
  Tax Planning for Troubled Businesses and Investments1:42:48
  Slides: Tax Planning for Troubled Businesses and InvestmentsPDF
  Tax Planning for Troubled Businesses and Investments Glossary/ IndexPDF