Tax Defense Guide
When Do You Need a Tax Attorney?
Sam Brotman, J.D., LL.M.
- An IRS agent has contacted you directly or requested a meeting
- Criminal exposure is possible, even as a background concern
- The amount in dispute is significant or the position is legally complex
- You need communications to be protected by attorney-client privilege
- You’ve received a Notice of Deficiency or are considering Tax Court
The Short Answer
A CPA handles compliance — preparing returns, applying accounting rules, representing you in routine IRS examinations. An attorney handles disputes, privilege, formal legal positions, and criminal exposure. The two roles overlap in some areas, but they’re not interchangeable.
You need a tax attorney when the problem has legal consequences — not just accounting ones.
The distinction matters because it shapes what kind of representation is appropriate, what protections you have, and what options remain available to you. Most people who end up needing an attorney don’t recognize the shift when it happens. An audit that starts as a documentation review can change character when the auditor begins asking about intent. A balance due can escalate when the IRS files a federal tax lien and begins levy action. A business transaction that seems straightforward can expose meaningful legal risk when the underlying position is examined.
None of this requires a crisis to be true. The scenarios below are the ones where an attorney’s specific capabilities — legal privilege, formal legal opinions, Tax Court representation — are what actually matters.
Scenario 1: An IRS Examination Has Become Adversarial
Routine audits are often handled by CPAs. But when the auditor is asking questions that suggest the IRS is looking beyond a return adjustment — questions about intent, about the source of funds, about whether you knew something — the examination has changed character.
An eggshell audit is one where civil and criminal exposure exist simultaneously. Your CPA’s job is to answer the auditor’s questions accurately; your attorney’s job is to protect your legal position while that happens. Those goals aren’t identical, and in a sensitive audit they can conflict.
The term “eggshell” reflects the fragility of the situation: one wrong statement, one document produced without consideration of its implications, one meeting where the wrong information is volunteered — and the civil examination can become the foundation for a criminal referral. Attorneys who handle these cases manage information flow deliberately. That’s a legal function, not an accounting one.
Signs that an audit has shifted character include: questions about lifestyle or spending that exceed the return items under examination; requests for bank records across multiple accounts and years; inquiries about specific transactions the taxpayer didn’t volunteer; and the involvement of a revenue agent accompanied by a technical specialist. Any of these signals a change worth addressing with counsel.
Related: Eggshell Audit Defense
Scenario 2: Criminal Exposure Is Possible
If an IRS Special Agent has contacted you, your attorney, your CPA, or your bank — stop. That’s IRS Criminal Investigation. Special Agents investigate tax crimes: evasion, fraud, willful failure to file, money laundering with tax components.
You have the right to remain silent. Anything you say to an IRS Special Agent can be used against you. The IRS does not send Special Agents on routine audits.
IRS Criminal Investigation handles federal tax felonies under Title 26 and related statutes. The penalties for conviction are severe: tax evasion under IRC §7201 carries up to five years in federal prison and a $250,000 fine. Filing a false return under IRC §7206(1) carries up to three years. These aren’t administrative penalties — they’re federal criminal charges.
The appropriate response to Special Agent contact is straightforward: do not speak with the agent; contact a criminal tax attorney; preserve all documents exactly as they are. What you should not do is call the IRS to explain, meet with the agent to clear things up, or assume that cooperation without counsel will benefit you. It typically doesn’t.
Related: Criminal Tax Defense · IRS Special Agent Contact
Scenario 3: Attorney-Client Privilege Matters
Communications between you and your tax attorney are protected by attorney-client privilege. Communications between you and your CPA are not — unless the CPA is operating under a Kovel arrangement retained by counsel.
If the IRS later issues a summons, your attorney’s files are protected. Your CPA’s work files are not. In sensitive situations — disputes where you’re considering an aggressive position, planning a transaction with meaningful tax risk, or dealing with an audit that could turn criminal — that distinction is the difference between what the IRS can and cannot compel.
A Kovel arrangement, named for the Second Circuit case United States v. Kovel, allows a taxpayer to retain an accountant through their attorney so that the accountant’s work falls within the attorney-client privilege umbrella. The accountant assists the attorney in rendering legal advice — rather than providing independent accounting advice to the taxpayer — which is what makes the privilege apply.
This structure is used regularly in complex audits, sensitive planning transactions, and any situation where the factual record needs careful management. It requires intentional setup; you can’t retrofit it after the IRS has already issued a summons. The time to build the privilege structure is before the problem surfaces, not after.
Scenario 4: You’ve Received a Notice of Deficiency
A Notice of Deficiency (90-day letter) is the IRS’s formal determination that you owe additional tax. It starts a 90-day clock. If you don’t file a petition in the U.S. Tax Court within that window, the IRS assessment becomes final and you lose your prepayment right to judicial review.
Tax Court is federal court. You can file pro se, but contested cases involve legal argument, evidentiary issues, and formal motion practice. An attorney who handles Tax Court cases is worth consulting before that 90-day window closes.
The notice of deficiency is one of the most time-sensitive documents in tax law. The 90-day deadline is statutory and jurisdictional — the Tax Court cannot accept a late petition regardless of the reason for the delay. If you’re outside the United States when the notice is issued, the deadline is 150 days.
Once the petition is filed, the case is docketed and the IRS Office of Chief Counsel is assigned. At that point, the case may settle through negotiation with IRS counsel, proceed through a trial (typically a small tax case for amounts under $50,000, or a regular case for larger amounts), or be resolved by summary judgment. The procedural rules are those of a federal court, not an administrative agency.
Related: Notice of Deficiency · Tax Litigation
Scenario 5: The Transaction Involves Meaningful Legal Uncertainty
Complex business transactions — sales, restructurings, §1031 exchanges with related-party issues, QSBS positions, exit planning — involve tax positions where the law isn’t settled or the facts need careful legal framing.
A tax attorney can provide a formal opinion letter that establishes a reasonable cause defense to accuracy-related penalties under IRC §6662. A CPA’s memo doesn’t carry the same weight.
The accuracy-related penalty under IRC §6662 applies when there’s a substantial understatement of tax (generally, more than the greater of 10% of the correct tax or $5,000). The reasonable cause exception under IRC §6664(c) applies when the taxpayer relied in good faith on the advice of a tax professional. The quality of the advice — and who provided it — matters in determining whether the exception applies.
An attorney’s formal opinion letter, particularly a “should” or “more likely than not” opinion on a disclosed position, provides penalty protection that a CPA’s analysis typically doesn’t. This is especially relevant in transactions involving significant tax positions: QSBS exclusion under IRC §1202, like-kind exchanges under IRC §1031, S corporation built-in gains, partnership allocations, and estate planning transactions.
Related: Business Sale Tax Attorney · Tax Advisory & Opinion Letters
When You Probably Don’t Need an Attorney
A routine audit of a simple return. A CP2000 notice about a 1099 mismatch you can explain. An installment agreement on a balance you don’t dispute. A first-time penalty abatement request on a straightforward filing failure.
A good CPA handles these well. The question isn’t whether you want an attorney — it’s whether the situation requires one.
The line is roughly this: when the problem is primarily about numbers and documentation, a CPA is appropriate. When the problem involves legal position, privilege, potential criminal exposure, judicial proceedings, or a formal legal opinion, an attorney is the right call. The two aren’t mutually exclusive — in complex matters, both work together — but they serve different functions.
If you’re uncertain which side of that line you’re on, a 15-minute call with a tax attorney is usually enough to find out. At Brotman Law, that call is free and doesn’t commit you to anything.
Questions about your specific situation?
Book a free 15-minute call. We’ll tell you whether you need an attorney, a CPA, or both.
Frequently Asked Questions
Can a CPA represent me in Tax Court?
Is an enrolled agent the same as a tax attorney?
What if my situation involves both accounting and legal issues?
When is it too late to bring in an attorney?
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