10 shaky tax deductions

According to the IRS, these ten tax deductions are among those most frequently taken by tax filers and then later challenged and denied by the Service:

  1. Dependents
  2. Daughter’s wedding
  3. Speeding ticket
  4. Charitable donations
  5. Hobbies
  6. Expenses to improve appearances
  7. Home loss as investment loss
  8. Home office deductions
  9. Boats
  10. Entertainment expenses

It is not that these deductions would never be allowed in any circumstance but rather that taxpayers often do not meet the requirements to substantiate the deductions. In those cases the deduction is disallowed and an additional penalty and interest applies.


Opinions expressed are solely those of the author and do not represent the position of any other person, company or entity mentioned in the article. Information is from sources believed to be reliable but cannot be guaranteed. Any accounting, business or tax advice contained in this communication, including attachments and enclosures, is not intended as a thorough, in-depth analysis of specific issues or a substitute for a formal opinion, nor is it sufficient to avoid tax-related penalties. Tony Novak operates as an independent adviser under the trademarks “Freedom Benefits“, “OnlineAdviser” and “OnlineNavigator” but is not a representative, agent, broker, producer or navigator for any securities broker dealer firm, federal or state health insurance marketplace or qualified health plan carrier. He has no financial position in any stocks mentioned. Novak does work as an accountant, agent, adviser, writer, consultant, marketer, reviewer, endorser, producer, lead generator or referrer to other companies including the companies listed in the articles on this web site.

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