Ethics of Tax Lawyering
by

Michael Hatfield
Professor of Law
University of Washington

March 2015

ii

About the Author

Michael Hatfield is a Professor of Law at University of Washington School
of Law. Previously he was a Professor of Law at Texas Tech University
where he served as the Associate Dean for Faculty Development and Research
and held the Glenn D. West Research Professorship. Michael has served as a

Visiting Professor of Law at the University of Washington School of Law
and at the Seattle University School of Law, and worked as an associate at
Debevoise & Plimpton in New York, New York and at Simpson, Thacher
& Bartlett in New York, New York. From 2010-2012, Michael served as
the Glenn D. West Research Professor at Texas Tech University. In 2010,
he was awarded the Texas Tech University President's Excellence in
Teaching Award, and in 2006, 2008, 2009, 2011, and 2012 he was named
the Outstanding Professor of the Year. In 2007 he was awarded the Texas
Tech University Alumni Association New Faculty Award. He teaches
courses in taxation, ethics, and trusts and estates. His research has been
published in the Florida Tax Review, the Northwestern Law Review
Colloquy, the NYU Annual Survey of American Law, the Baylor Law
Review, the Notre Dame Journal of Ethics and Public Policy, the Lewis &
Clark Law Review, the Texas Tech Law Review, Tax Notes and the Johns
Hopkins University Press. With Baylor Law School Mills Cox Professor of
Law Thomas M. Featherston, Jr. he co-authored Q&A: Wills, Trusts and
Estates (2nd. ed., 2008).

iii

Notices

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This material does not contain nor is intended to be legal advice. Users
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About CALI eLangdell Press

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vi

Table of Contents
About the Author ................................................................................... iii
Notices ....................................................................................................iv
About CALI eLangdell Press .................................................................vi
Table of Contents ..................................................................................vii
1. Introducing Legal Ethics for Tax Lawyers ........................................ 1
1.1. Ethics for Lawyers ........................................................................... 1
Notes and Questions ................................................................................................ 2
1.2. The Duty to the Tax System ...........................................................3
Notes and Questions ................................................................................................ 3
1.3. Sharing the Profession with Non-Lawyers .....................................3
Grace v. Allen ............................................................................................................. 4
Notes and Questions ................................................................................................ 8

2. Regulating Tax Lawyering ............................................................... 11
2.1. Regulating Tax Lawyering through the IRC ................................ 11
IRC § 7206. Fraud and false statements ............................................................12
Notes and Questions ..............................................................................................12
§ 6694. Understatement of taxpayer's liability by tax return preparer .......14
Notes and Questions ..............................................................................................19
2.2. Regulating Tax Lawyering through Circular 230 ......................... 21
Notes and Questions ..............................................................................................32
WASHBURN v. SHAPIRO .................................................................................35
2.3. Regulating Tax Lawyering through Malpractice Standards ........ 36

3. Ethical Problems for Tax Lawyers .................................................. 39
3.1. Tax Opinions and Tax Shelters .................................................... 39
Notes and Questions ..............................................................................................43

vii

3.2. Mistakes ........................................................................................ 43
Notes and Questions ..............................................................................................45
3.3. Working with IRS Lawyers and Other Employees ....................... 46
§ 10.51 Incompetence and disreputable conduct............................................48
Internal Revenue Manual 4.1.1.7.6.1 - Badges of Practitioner Abuse (0520-2005)......................................................................................................................49
From 1991-2 C.B. 1137:.........................................................................................50
Notes and Questions ..............................................................................................51

viii

1. Introducing Legal Ethics
for Tax Lawyers
In order to appreciate the ethical complications in which tax lawyers
often find themselves, it is essential to appreciate and understand the
greater contexts of legal ethics and the tax system. While it is
important to begin with this more general discussion of ethics and
tax lawyers, it may also be useful to re-read this section after finishing
the chapter—to get a view of the forest after inspecting some of the
trees.
1.1. Ethics for Lawyers
Ethics is practical reasoning. It is thinking through the most
important implications of behavior. For lawyers, ethical reflection
involves considering not only the lawyer’s personal values but also
the lawyer’s roles as officers in the legal system and as agents and
advisors for clients. Organizing and clarifying the layers of
obligations and duties implicated in lawyer behavior is the subject
matter of legal ethics. The objective is to define a lawyer’s
professional responsibilities. It is not an abstract or idealistic exercise.
A lawyer with a misunderstanding of her professional responsibilities
may find herself disbarred from the practice of law, sued by her
former clients, fined and jailed—personally miserable even if she
escapes discipline, suit, or criminal punishment.
Many ethical considerations reflect a lawyer’s personal values, such as
the choice of practice area or choice of clients. However, legal ethics
is not simply the domain of personal values. A great many duties are
imposed on lawyers by fiduciary and contract laws, and, of course,
each state has its own ethics rules and means of enforcement. Most
states have adopted some version of the American Bar Association’s
Model Rules of Professional Conduct, and many have followed the
ABA’s subsequent amendments (as amended, the “Model Rules.”).
While the popular image of a lawyer may be as a courtroom strategist
and dramatist focused on winning at any cost, the Model Rules reflect
the complex realities of lawyering, prescribing different standards for

a lawyer working as an advisor, neutral third party, and advocate, as
well as unavoidable duties to third parties, opposing counsel, and the
tribunal.
Unfortunately for the practicing lawyer, burdened with thinking
through the consequences of her professional behavior, complying
with the state ethics rules does not necessarily mean she escapes
liability under malpractice standards. Lawyers may be sued by former
clients—and even third parties who were never clients—on either
tort or contractual grounds where compliance with the state ethics
rules may not provide a sufficient defense. Although the different
standards used in disciplinary and malpractice claims may appear to
be confusing, a prudent lawyer should never close her eyes, rely on
untutored intuition, and hope for the best.

Notes and Questions
1. Under the Model Rules, what are the differences between a
lawyer acting as an advisor and a lawyer acting as an advocate?
Has the state in which you intend to be admitted adopted the
ABA Model Rules? The Tax Court has adopted the Model
Rules—both their “letter and spirit.” United States Tax Court
Rules of Practice Rule 202(a)(3). What does “spirit” mean? How
does one comply with the “spirit” when it is not described in the
“letter?” We may speak in these terms in casual conversation, but
if you are the lawyer needing to know how to proceed in court,
how do you determine if “letter” and “spirit” have different
requirements? If the requirements are the same, why mention
both? If the requirements are not the same, how do you know? Is
your client’s interest relevant in determining the “spirit” of the
Model Rules?
2. Due to the cost of legal advice, tax advice from a lawyer is rarely
justified unless a substantial dollar amount is involved. What does
that mean about the amount of damages likely to be sought in a
tax malpractice suit?

2

1.2. The Duty to the Tax System
Tax lawyers may be disciplined by the authorities where they are
admitted to practice; they also risk malpractice suits for negligence
and otherwise failing to fulfill fiduciary or contractual duties to clients
or others. Furthermore, they may be subject to discipline by the
Internal Revenue Service (the “IRS”) under extensive written
regulations (usually referenced as “Circular 230”). 1 Under these
regulations, the minimum standard for advice as to an undisclosed
tax return position is “substantial authority,”2 which is often
described as “around a 40% chance of success on the merits.” 3 This
standard has no counterpart in the Model Rules, and is much higher
than the non-frivolous standard for advocacy under ABA Model Rule
3.1.
Such standards for tax lawyers are often described as the tax lawyer’s
“duty to the system.”4 This duty reflects the self-reporting nature of
our tax system in which only 1–2% of tax returns are audited. It
requires ignoring the low audit rate. Tax advice must be given on the
presumption that the issue will be litigated in court rather than
gambling that the IRS will never examine the issue (playing “audit
roulette,” as it is often called). 5 After all, with a 2% audit rate, even
the worst tax advice has a 98% chance of “succeeding” (as 98% of
tax returns are not audited).

Notes and Questions
3. If 100% of tax returns were thoroughly audited, would it be
relevant in terms of tax lawyers’ duty to the system? What would
be the duty to the system if returns were never audited?
4. What if criminal defense lawyers had to have “substantial
authority” for every legal argument made on behalf of their
clients? What are some of the differences between advising as to
tax return positions and advising as to criminal defense?

1.3. Sharing the Profession with Non-Lawyers
Tax lawyers share the tax field with Certified Public Accountants
(“CPAs”). Federal law authorizes both lawyers and CPAs to
represent clients before the IRS, 6 where both practice before the IRS

3

and are regulated by the Secretary of the Treasury. 7 Further, so long
as they pass an examination, Rule 200(a)(3) of the United State Tax
Court Rules of Practice authorizes CPAs to represent clients before
the Tax Court.
Grace v. Allen
407 S.W.2d 321 (Tex. Civ. App. 1966)

BATEMAN, Justice. This is a suit to recover the value of
accountants’ services performed…. Appellants pled, Inter
alia, that appellees were not entitled to recover because their
alleged services constituted the unauthorized practice of
law…. The trial court rendered judgment for appellees for the
total of $12,600, and appellants appeal on two points of error.
The first of these is that the court erred in holding as a matter
of law that the services rendered by appellees did not
constitute the practice of law…. Appellees contend that their
services in question did not constitute the practice of law . . .,
and that in any event such services were within the purview
of the federal law and Treasury Department regulations; that
although not members of the Bar, they were licensed to
practice before the Treasury Department, that everything they
did was pursuant to and in accordance with that license, and
that if their services were proscribed under New York law
they were fully authorized by the federal law and Treasury
regulations and, therefore, lawful….
There is no substantial dispute as to the facts. Appellees were
both licensed public accountants, one of them being certified,
and both were admitted to practice before the Treasury
Department, although neither of them was a lawyer. Both of
them had been employed by the Internal Revenue Service for
a number of years before entering private practice. Although
the appellees had not prepared the appellants’ income tax
returns for the years 1955, 1956, 1957 and 1958, when the
Internal Revenue Service assessed additional taxes for those
years they were employed to work with appellants' attorneys
in New York City in the preparation and presentation of a

4

protest of such assessment. They did so, and it is these
services which appellants say constituted the unauthorized
practice of law, pointing out that one of the appellees testified
that ‘complicated issues’ were involved, that the protest cited
numerous cases as authority for the position they were taking,
some of which cases had been discussed with the lawyers but
some of which had been found as a result of research by the
appellee Brown. Appellees had prepared in their office several
Forms 872, ‘Consent to Extension of the Statute of
Limitations,’ also memoranda used and presented in various
conferences, with representatives of the Internal Revenue
Service. Appellees conferred frequently with appellants’
attorneys and kept them advised by telephone and mail as to
audits by the Internal Revenue Service and the preparation of
the protest. The attorneys participated and cooperated in the
preparation of the protest and in conferences with the
Internal Revenue Service examining agent and conference
coordinator. Appellees also prepared a power of attorney
authorizing the attorneys to act for appellees in connection
with audits of appellants’ tax returns. Appellants employed
appellees to prepare and file their Federal and New York
State income tax returns for 1960 and their declarations of
estimated income tax (Federal and State) for 1961; also to
maintain appellants’ proper books and records therefor.
To support their position that under New York law the work
done by appellees constituted unauthorized law practice,
appellants rely wholly on the case of In the Matter of New
York County Lawyers Association (Bernard Bercu,
Respondent), 273 App. Div. 524, 78 N.Y.S.2d 209, 9
A.L.R.2d 787. In that case . . . the court recognized that an
accountant employed to keep a taxpayer’s books or prepare
his tax return would be expected and permitted to answer
legal questions arising out of and incidental to the accounting
work. The court also recognized that the matter of taxation,
‘which permeates almost every phase of modern life, is so
inextricably interwoven with nearly every branch of law that

5

one could hardly pick any tax problem and say this is a
question of pure taxation or pure tax law wholly unconnected
with other legal principles, incidents or ramifications.’
Recognizing the necessity of drawing a line of demarcation
between the work of the tax lawyer and that of the tax
accountant, the court said, ‘the point at which it must be
drawn, at very least, is where the accountant or non-lawyer
undertakes to pass upon a legal question apart from the
regular pursuit of his calling.’. . .
However, in the case at bar it is not shown that appellants
consulted appellees or sought or obtained their opinion on
any legal subject that was not incidental to their accounting
work. Appellees were preparing the appellants’ 1960 income
tax returns and were the regular accountants for appellants.
They were also doing accounting work in reviewing and
classifying the great volume of papers and records of
appellants necessary to the preparation of the protest of the
tax assessment and to enable them to discuss with the
Revenue Agents the asserted tax liability. It is true that in the
preparation of the protest appellees cited numerous cases in
support of their position, but this was necessary and
incidental to the preparation and presentation of the protest.
Moreover, appellees consulted the appellants’ attorneys
concerning these authorities and other aspects of the work
being done and kept them informed as the work progressed. .
..
It is clear from the record before us that the work performed
by appellees, which appellants assert constituted the
unauthorized practice of law, was only incidental to their
accounting work and was therefore permissible and not
unlawful under New York law.
Appellees assert, and appellants do not deny, that the work
done by appellees was all within the purview of their licenses
to practice before the Treasury Department. It was agreed on
the trial that the court might take judicial notice of the federal

6

law and Treasury regulations on the subject. One of those
regulations, in part, provides:
Practice before the Internal Revenue Service
comprehends all matters connected with
presentations to the Internal Revenue Service
or any of its officers or employees relating to
a client’s rights, privileges, or liabilities under
laws or regulations administered by the
Internal Revenue Service. Such presentations
include the preparation and filing of necessary
documents, correspondence with, and
communications to the Internal Revenue
Service, and the representation of a client at
conferences, hearings, and meetings.
Appellees take the position that if there is a conflict between
the state law and the federal law, the former must yield, and
that, since the regulations referred to were promulgated under
sanction of the federal law, they have the force and effect of
law. We agree with appellees. The rights conferred by the
admission to practice before the Treasury Department are
federal rights which cannot be impinged upon by the states in
their praiseworthy efforts to protect their citizens from
unskilled and unethical practitioners of the law. Sperry v.
State of Florida ex rel. Florida Bar, 373 U.S. 379, 83 S. Ct.
1322, 10 L. Ed.2d 428.
This is not to say that the states have surrendered their right
to regulate and control the practice of law within their
respective boundaries, as was done in the Bercu case. See also
Hexter Title & Abstract Co. v. Grievance Committee, 142
Tex. 506, 179 S.W.2d 946, 157 A.L.R. 268. In fact, one of the
Treasury regulations referred to (§ 10.39) contains this
proviso: ‘And provided further: That nothing in the
regulations in this part shall be construed as authorizing
persons not members of the Bar to practice law.’ See also
Free v. Bland, 369 U.S. 663, 82 S. Ct. 1089, 8 L. Ed.2d 180;
Hatfried, Inc. v. Commissioner of Internal Revenue, 3 Cir.,
162 F.2d 628; Haywood Lumber & Mining Co. v.

7

Commissioner of Internal Revenue, 2 Cir., 178 F.2d 769;
Burton Swartz Land Corp. v. Commissioner of Internal
Revenue, 5 Cir., 198 F.2d 558. Appellants' first point is
overruled….
Finding no error requiring reversal, we affirm the judgment
of the trial court.

Notes and Questions
5. The Grace court cites Sperry v. State of Florida ex rel. Florida Bar, 373
U.S. 379, 83 S. Ct. 1322, 10 L. Ed.2d 428 (1963). The Sperry case
involved a practitioner authorized to practice before the U.S.
Patent Office, but not authorized to practice law in Florida,
which is where he maintained his office. Federal law authorizes
non-lawyers to practice before the U.S. Patent Office. May
someone who is not admitted to practice law in the state in which
he has offices engage in the practice of tax law? How can federal
tax issues and state law issues, such as corporate, creditor, and
property issues, be separated in any practical sense? For example,
if a tax issue requires determination of the nature of an
underlying property right under state law, is someone authorized
to practice tax entitled to opine as to the underlying state law
issue? Or is it that someone authorized to practice tax law is
entitled to opine as to the tax law issue, only if someone else, who
is authorized to practice state law, has opined on the state law
issue? What does Circular 230 § 10.39 mean? As to Circular 230,
see below.
6. What do CPAs do? The National Conference of Lawyers and
Certified Public Accountants issued a study on the relationship
between lawyers and CPAs. Like lawyers, CPAs are licensed to
practice by state professional boards. CPAs engage in accounting
and auditing, tax and management consulting, and especially in
expert examination of financial statements. They develop and
analyze data, especially data expressed in monetary or other
quantitative forms. 8
7. What do lawyers do? Trying to define the “practice of law” in
order to prohibit the unauthorized practice of law has consumed

8

many courts, and few generalizations are useful. Many nonlawyers routinely interpret, apply, and discuss the consequences
of the law (e.g., consider bank employees who advise customers
on the survivorship rights in accounts). Many non-lawyers
routinely prepare legally-binding documents (e.g., consider real
estate agents who prepare sales contracts). And many nonlawyers represent others before agencies (e.g., the U.S. Patent
Office) and in court (e.g., the U.S. Court of Appeals for Veterans
Claims).
8. If CPAs and tax lawyers share the tax field, how is the work
divided? Both may prepare tax returns, though, in practice, few
tax lawyers specialize in routinely preparing income tax returns
for clients. With respect to ascertaining the “probable tax effects
of transactions,” the National Conference of Lawyers and
Certified Public Accountants (“The Conference”) recognize that
both lawyers and CPAs are qualified, but urge CPAs to consult
lawyers when there are uncertainties as to the interpretation or
application of laws, and urge lawyers to consult CPAs when there
are uncertainties as to describing the transaction in money terms
or interpreting financial results. 9 The Conference identifies
preparing legal documents as part of the special training of
lawyers, and the preparation of financial statements and similar
reports as part of the special training of accountants. 10 The
Conference recognizes the opportunity for CPAs to represent
clients before the Tax Court, but, noting that the client may also
pursue remedies in a District Court or the Court of Claims,
suggests that a lawyer be consulted when the IRS issues a notice
of deficiency. 11
9. The Conference concludes that all matters involving criminal
investigations should be referred to lawyers. 12 Why?
10. Usually we think of lawyers as having a monopoly on advising
clients on legal issues and representing clients in court. However,
CPAs are authorized to advise clients on the tax law, and CPAs
are authorized to represent clients in Tax Court. We also usually
think of lawyers as an independent profession—one that
regulates itself. However, tax lawyers, like CPAs, are regulated by

9

the Treasury Department. What is the essence of being a lawyer?
Would it make more sense to classify tax lawyers as part of a “tax
profession” shared with CPAs? Are tax lawyers and medical
malpractice lawyers or criminal defense lawyers members of a
shared profession in any meaningful sense?

10

2. Regulating Tax Lawyering
Lawyers often think of the legal profession’s uniqueness as inhering
in—or reflecting—the profession’s self-regulated nature and its
monopoly on certain services, such as representing clients in courts.
Yet, for tax lawyers, matters are quite different. Whereas most
lawyers are subject to regulation only by the state authorities where
they are admitted and the federal courts in which they practice,
Congress has enacted parts of the Internal Revenue Code to
prescribe tax lawyering standards. Tax lawyers may be subject to both
civil and criminal penalties as a result of their tax advice. The
Treasury Secretary exercises authority over tax lawyers through
Director of the Office of Professional Responsibility (the “OPR”)
and Circular 230. CPAs who “practice tax” are also subject to the
OPR and Circular 230. Unlike most other lawyers, tax lawyers share
their profession with non-lawyers and are regulated by non-lawyers.

2.1. Regulating Tax Lawyering through the IRC
A taxpayer has the right to structure his affairs so as to minimize his
tax liabilities. This is the right to avoid unnecessary taxation, that is,
taxes he is not obligated to pay. However, a taxpayer commits a
felony if he willfully attempts to evade or defeat taxes he is obligated
to pay. Under I.R.C. § 7201, such a taxpayer may be fined $100,000
and imprisoned for up to five years. Of course, lawyers may not
engage in assisting clients in any criminal behavior, including tax
evasion. Model Rule 1.2(d). But where is the line between legal tax
avoidance (for which tax lawyers are well-paid) and criminal tax
evasion (which can land both client and tax lawyer in prison)?
Generally, criminal tax evasion requires that the taxpayer knew her
obligations under the tax law but intentionally did not fulfill those
obligations. In other words, ignorance of the tax law is a defense to
criminal conviction. See, e.g., United States v. Harris, 942 F.2d. 1125
(7th Cir. 1991) (mistresses who received payments but argued
exclusion as “gifts” were not criminally liable for tax evasion as the
prevailing legal standard was too unclear to establish willful evasion).
A civil fraud penalty may also apply. I.R.C. § 6663.

Willfully filing a return that the taxpayer does not believe is true and
correct as to every material matter is a felony punishable by up to
$100,000 and imprisonment for up to three years. I.R.C. § 7206(a)(1).
So is aiding or assisting anyone in doing so:
IRC § 7206. Fraud and false statements
Any person who-***
(2) Aid or assistance.--Willfully aids or assists
in, or procures, counsels, or advises the
preparation or presentation under, or in
connection with any matter arising under, the
internal revenue laws, of a return, affidavit,
claim, or other document, which is fraudulent
or is false as to any material matter, whether
or not such falsity or fraud is with the
knowledge or consent of the person
authorized or required to present such return,
affidavit, claim, or document; […]
***
shall be guilty of a felony and, upon
conviction thereof, shall be fined not more
than $100,000 ($500,000 in the case of a
corporation), or imprisoned not more than 3
years, or both, together with the costs of
prosecution.

Notes and Questions
11. Note that § 6701 provides a civil penalty for aiding and abetting a
tax liability understatement that is very similar to the § 7206(a)(2)
criminal penalty.
12. A lawyer who prepares tax-related documents that are
“fraudulent” or “false as to any material matter” may be
committing a felony under § 7206(a)(2). The false statement need
not be material to calculating the tax liability. U. S. v. Abbas, 504
F.2d 123 (9th Cir. 1974), certiorari denied 95 S. Ct. 1990, 421 U.S.
988, 44 L. Ed.2d 477 (1975). Of course, if the return is audited

12

and the falsity discovered, no tax will be successfully evaded.
However, success in evasion is not relevant. U.S. v. Borgis, 182
F.2d 274 (7th Cir. 1950). Note that § 7206(a)(2) applies to “any
person,” not only a preparer of the return. For example, an
engineer who prepared a fraudulent report about coal reserves,
knowing the report would be used in claiming undue tax benefits,
violated § 7206(a)(2). U.S. v. Nealy, 729 F.2d 961 (4th Cir. 1984).
13. Laura is a second year associate in the tax department of a large
law firm. A corporate client was involved in a merger. It was
essential for the best tax consequences that the merger be
completed on July 1, as this was the first day of the fiscal year for
the parties involved. For two months prior to this deadline,
Laura, along with many of the other lawyers involved, worked 80
hour weeks. The deal seemed to be completed as planned.
However, over the July 4th holiday, the junior partner supervising
Laura asked her into his office. He told her that several
documents that should have been executed on July 1 had not
been. He instructed Laura to prepare the documents with a July 1
date, and that he would send the documents by courier to the
client for immediate execution. If Laura knows that the
documents will be used in preparing the client’s tax returns, is she
committing a § 7206(a)(2) felony if she follows the instructions?
Would she be subject to the IRC § 6701 civil penalty if she
follows the instructions? What if Laura is unsure how these
particular documents relate to the tax return? What if she asks the
partner, and he tells her that it is a good question but not to
worry about it? What if, instead of telling her not to worry about
it, he explains that the documents are very useful for
“housekeeping” purposes but not essential to the tax treatment
and not a material matter for tax purposes? Does Model Rule 5.2
apply? Would complying with the Model Rules protect Laura
from criminal prosecution? Being convicted under § 7206(a)(2)
may lead to being permanently disbarred by the Secretary of the
Treasury (and the state bar). See the Washburn case below.
14. There are multiple IRC sections that impose criminal sanctions.
Review IRC §§ 7201–17. There are also criminal provisions

13

elsewhere in federal law that may apply when tax lawyers assist
their clients in crossing the line from tax avoidance into tax
evasion, such as conspiracy to defraud the United States (18
U.S.C. § 371 (2012)) or making false statements to the federal
government (18 U.S.C. § 1001 (2012)). The mailing of a
fraudulent tax return may be a mail fraud felony (18 U.S.C. §§
1341, 1343 (2012)), which may be a predicate crime for
prosecution under the RICO Act (18 U.S.C. §§ 1341–51 (2012)).
At what point does advising a client on minimizing taxes become
a conspiracy between the lawyer and client to defraud the federal
government of its property? Would it be a prudent office
procedure to avoid mailing tax returns on behalf of clients?
While the criminal penalties and civil fraud penalties for tax evasion
raise many interesting issues, most taxpayers do not willfully evade
their tax liabilities or commit fraud. In fact, American taxpayers
willfully pay the taxes they owe at a rate that is very high compared to
others in the world (about 85%). Most American taxpayers want to
“get it right,” it seems. But given the complexities of tax law, they
may not be able to do so. The tax law is a strict liability law: taxpayers
owe what they owe regardless of their knowledge or intention. When
a client turns to a tax lawyer for advice, the client should be able to
rely on the advice, expecting it to be accurate.
IRC § 6694(a) is prominent in regulating the advice tax lawyers give
in connection with tax return preparation. It sets a relatively high
standard for the advice, and it imposes a penalty on a tax return
preparer if there is an “unreasonable position” on the return that
results in an understatement of tax liability.
§ 6694. Understatement of taxpayer's liability by tax
return preparer
(a) Understatement due to unreasonable
positions.
(1) In general.—If a tax return preparer—
(A) prepares any return or claim of
refund with respect to which any
part of an understatement of

14

liability is due to a position
described in paragraph (2), and
(B) knew (or reasonably should
have known) of the position, such
tax return preparer shall pay a
penalty with respect to each such
return or claim in an amount equal
to the greater of $1,000 or 50
percent of the income derived (or
to be derived) by the tax return
preparer with respect to the return
or claim.
(2) Unreasonable position.—
(A) In general.—Except as
otherwise provided in this
paragraph, a position is described
in this paragraph unless there is or
was substantial authority for the
position.
(B) Disclosed positions.—If the
position was disclosed as provided
in section 6662(d)(2)(B)(ii)(I) and
is not a position to which
subparagraph (C) applies, the
position is described in this
paragraph unless there is a
reasonable basis for the position.
***
(3) Reasonable cause exception.—No penalty
shall be imposed under this subsection if it is
shown that there is reasonable cause for the
understatement and the tax return preparer
acted in good faith.
IRC § 6694(a)(2)(A) and (B) secure two types of positions from being
characterized as “unreasonable.” First are positions for which there is
“substantial authority.” Second are positions for which there is a

15

“reasonable basis” and were disclosed on IRS Form 8275 or 8275-R.
But what does “substantial authority” and “reasonable basis” mean?
“Substantial authority” is often thought to mean “around a 40%
chance of success on the merits.”13 According to IRS Notice 2009-5,
“substantial authority” has the same meaning under IRC § 6694 as in
§ 1.6662-4(d)(2) and (d)(3) which provides as follows:
(2) Substantial authority standard. The
substantial authority standard is an objective
standard involving an analysis of the law and
application of the law to relevant facts. The
substantial authority standard is less stringent
than the more likely than not standard (the
standard that is met when there is a greater
than 50-percent likelihood of the position
being upheld), but more stringent than the
reasonable basis standard as defined in §
1.6662-3(b)(3). The possibility that a return
will not be audited or, if audited, that an item
will not be raised on audit, is not relevant in
determining whether the substantial authority
standard (or the reasonable basis standard) is
satisfied.
(3) Determination of whether substantial
authority is present–
(i) Evaluation of authorities. There is
substantial authority for the tax treatment
of an item only if the weight of the
authorities supporting the treatment is
substantial in relation to the weight of
authorities supporting contrary treatment.
All authorities relevant to the tax
treatment of an item, including the
authorities contrary to the treatment, are
taken into account in determining whether
substantial authority exists. . . . There may
be substantial authority for more than one
position with respect to the same item.
Because the substantial authority standard

16

is an objective standard, the taxpayer's
belief that there is substantial authority for
the tax treatment of an item is not
relevant in determining whether there is
substantial authority for that treatment.
(ii) Nature of analysis. The weight
accorded an authority depends on its
relevance and persuasiveness, and the type
of document providing the authority. For
example, [an] authority that merely states a
conclusion ordinarily is less persuasive
than one that reaches its conclusion by
cogently relating the applicable law to
pertinent facts. . . . For example, a revenue
ruling is accorded greater weight than a
private letter ruling addressing the same
issue. An older [document] must be
accorded less weight than a more recent
one. Any document described in the
preceding sentence that is more than 10
years old generally is accorded very little
weight…. There may be substantial
authority for the tax treatment of an item
despite the absence of certain types of
authority. Thus, a taxpayer may have
substantial authority for a position that is
supported only by a well-reasoned
construction of the applicable statutory
provision.
(iii) Types of authority. [Generally, the]
following are authority for purposes of
determining whether there is substantial
authority for the tax treatment of an item:
Applicable provisions of the Internal
Revenue Code and other statutory
provisions; proposed, temporary and final
regulations construing such statutes;
revenue rulings and revenue procedures;
tax treaties and regulations thereunder;

17

and Treasury Department and other
official explanations of such treaties; court
cases; congressional intent as reflected in
committee reports, joint explanatory
statements of managers included in
conference committee reports, and floor
statements made prior to enactment by
one of a bill's managers; General
Explanations of tax legislation prepared
by the Joint Committee on Taxation (the
Blue Book); private letter rulings and
technical advice memoranda issued after
October 31, 1976; actions on decisions
and general counsel memoranda issued
after March 12, 1981 (as well as general
counsel memoranda published in pre1955 volumes of the Cumulative Bulletin);
Internal Revenue Service information or
press
releases;
and
notices,
announcements and other administrative
pronouncements…. Conclusions reached
in treatises, legal periodicals, legal
opinions or opinions rendered by tax
professionals are not authority. The
authorities underlying such expressions of
opinion where applicable to the facts of a
particular case, however, may give rise to
substantial authority for the tax treatment
of an item…. In the case of court
decisions, for example, a district court
opinion on an issue is not an authority if
overruled or reversed by the United States
Court of Appeals for such district.
However, a Tax Court opinion is not
considered to be overruled or modified by
a court of appeals to which a taxpayer
does not have a right of appeal, unless the
Tax Court adopts the holding of the court
of appeal....

18

A position with a “reasonable basis” is often thought to be one with
a 10–20% chance of success on the merits. 14 Though not as high a
standard as “substantial authority,” Treasury Regulations § 1.6662 3(b)(3) and § 1.6694-2(d)(2) provide that the “reasonable basis”
standard is a relatively high standard of tax reporting, that is,
significantly higher than not frivolous or not patently improper. The
reasonable basis standard is not satisfied by a return position that is
merely arguable or that is merely a colorable claim. If a return
position is reasonably based on one or more of the authorities set
forth above regarding substantial authority, the return position will
generally satisfy the reasonable basis standard even though it may not
satisfy the substantiality authority standard.

Notes and Questions
15. Although § 6694 only applies to a tax return preparer, the
definition of a “preparer” is broader than may be anticipated.
Even if a tax lawyer does not literally prepare the return, she may
be deemed to be a preparer by virtue of providing advice about
an entry on a return. In general, advice given prior to a
transaction does not turn a tax lawyer into a preparer but advice
given afterwards may. The distinction between “before” and
“after” advice is easy to maintain in theory, but may rarely hold in
practice—after all, there are often follow-up questions. Read
Treasury Regulations § 301.7701-15.
16. Laura is a tax lawyer who provides tax advice to a client in
connection with the sale of certain business assets. The client
consummates the transaction as advised by Laura. Laura’s total
time involved in the transaction is thirty hours. After the
transaction is completed, Laura has no additional contact with the
client. The client’s CPA prepares its tax return without consulting
Laura. Is Laura a “preparer” of that return? What if the client and
the client’s CPA call Laura for a thirty minute follow-up on some
of the tax issues so the CPA will know how to prepare the
return? What if the follow up requires fifteen additional hours of
work by Laura? What if the client did not consult with Laura
prior to the transaction but does so only afterwards?

19

17. How does a tax lawyer decide whether a position has a 20% or
40% chance of success if litigated? Why should a tax lawyer ever
be able to advise a client to take a position if the chances are that
a court would hold against the position? After all, at about 40%,
the substantial authority standard is considered a relatively high
standard of legal advice, by definition, the chances are still about
60% that it will lose in court. Could there be substantial authority
for conflicting positions?
18. Private letter rulings are not precedential. Why are they
considered “authority” for these purposes? What makes a treatise
or law journal authoritative?
19. A position for which there is only a “reasonable basis” will not be
considered unreasonable if the position is disclosed to the IRS by
attaching Form 8725 to the tax return. Review Form 8275. What
is the purpose of Form 8275?
20. The § 6694(a) penalty applicable is the greater of $1,000 or 50%
of the preparer’s fee. Other punishments may also apply. For
example, the tax lawyer may be disciplined pursuant to Circular
230, especially if there is a pattern of inappropriate advising. Note
also that § 6694(b) imposes a greater penalty if the
understatement was due to “willful or reckless conduct” rather
than a merely “unreasonable position.” See also Circular 230 §
10.51(13).
21. Alongside the “substantial authority” and “reasonable basis”
standards, there is also protection provided the preparer had
“reasonable cause” and acted in “good faith.” § 6694(a)(3).
Treasury Regulations § 1.6694-2(e) details this exception,
emphasizing factors such as whether or not the provision
involved was complex or highly technical; whether the error was
isolated or part of a pattern; and whether or not the “normal
office practice” of the preparer promotes “accuracy and
consistency.” This final factor emphasizes the importance of
good office practices, such as the routine use of checklists. Even
though a tax lawyer makes a mistake, the processes routinely used

20

in the office may turn out to be very important to providing
penalty protection.

2.2. Regulating Tax Lawyering through Circular 230
Consider the following sections of Circular 230:
§ 10.2 Definitions.
(a) As used in this part, except where the text
provides otherwise—
***
(4) Practice before the Internal Revenue
Service comprehends all matters connected
with a presentation to the Internal Revenue
Service or any of its officers or employees
relating to a taxpayer's rights, privileges, or
liabilities under laws or regulations
administered by the Internal Revenue
Service. Such presentations include, but are
not limited to, preparing and filing
documents,
corresponding
and
communicating with the Internal Revenue
Service, rendering written advice with
respect to any entity, transaction, plan or
arrangement, or other plan or arrangement
having a potential for tax avoidance or
evasion, and representing a client at
conferences, hearings and meetings.
***
§ 10.3 Who may practice.
(a) Attorneys. Any attorney who is not
currently under suspension or disbarment
from practice before the Internal Revenue
Service may practice before the Internal
Revenue Service….
(b) Certified public accountants. Any certified
public accountant who is not currently under
suspension or disbarment from practice

21

before the Internal Revenue Service may
practice before the Internal Revenue
Service….
***
§ 10.20 Information to be furnished.
(a) To the Internal Revenue Service.
(1) A practitioner must, on a proper and
lawful request by a duly authorized officer
or employee of the Internal Revenue
Service, promptly submit records or
information in any matter before the
Internal Revenue Service unless the
practitioner believes in good faith and on
reasonable grounds that the records or
information are privileged.
(2) Where the requested records or
information are not in the possession of, or
subject to the control of, the practitioner or
the practitioner's client, the practitioner
must promptly notify the requesting
Internal Revenue Service officer or
employee and the practitioner must provide
any information that the practitioner has
regarding the identity of any person who the
practitioner believes may have possession or
control of the requested records or
information….
***
§ 10.22 Diligence as to accuracy.
(a) In general. A practitioner must exercise
due diligence—
(1) In preparing or assisting in the
preparation of, approving, and filing tax
returns, documents, affidavits, and other
papers relating to Internal Revenue Service
matters;

22

(2) In determining the correctness of oral or
written representations made by the
practitioner to the Department of the
Treasury; and
(3) In determining the correctness of oral or
written representations made by the
practitioner to clients with reference to any
matter administered by the Internal
Revenue Service.
***
§ 10.27 Fees.
(a) In general. A practitioner may not charge
an unconscionable fee in connection with any
matter before the Internal Revenue Service.
(b) Contingent fees—
(1) Except as provided in paragraphs (b)(2),
(3), and (4) of this section, a practitioner
may not charge a contingent fee for services
rendered in connection with any matter
before the Internal Revenue Service.
(2) A practitioner may charge a contingent
fee for services rendered in connection with
the Service's examination of, or challenge
to—
(i) An original tax return; or
(ii) An amended return or claim for
refund or credit where the amended
return or claim for refund or credit was
filed within 120 days of the taxpayer
receiving a written notice of the
examination of, or a written challenge to
the original tax return.
(3) A practitioner may charge a contingent
fee for services rendered in connection with
a claim for credit or refund filed solely in
connection with the determination of

23

statutory interest or penalties assessed by
the Internal Revenue Service.
(4) A practitioner may charge a contingent
fee for services rendered in connection with
any judicial proceeding arising under the
Internal Revenue Code.
(c) Definitions. For purposes of this section—
(1) Contingent fee is any fee that is based, in
whole or in part, on whether or not a
position taken on a tax return or other filing
avoids challenge by the Internal Revenue
Service or is sustained either by the Internal
Revenue Service or in litigation. A
contingent fee includes a fee that is based
on a percentage of the refund reported on a
return, that is based on a percentage of the
taxes saved, or that otherwise depends on
the specific result attained. A contingent fee
also includes any fee arrangement in which
the practitioner will reimburse the client for
all or a portion of the client's fee in the
event that a position taken on a tax return
or other filing is challenged by the Internal
Revenue Service or is not sustained,
whether pursuant to an indemnity
agreement, a guarantee, rescission rights, or
any other arrangement with a similar effect.
(2) Matter before the Internal Revenue
Service includes tax planning and advice,
preparing or filing or assisting in preparing
or filing returns or claims for refund or
credit, and all matters connected with a
presentation to the Internal Revenue Service
or any of its officers or employees relating
to a taxpayer's rights, privileges, or liabilities
under laws or regulations administered by
the Internal Revenue Service. Such
presentations include, but are not limited to,

24

preparing
and
filing
documents,
corresponding and communicating with the
Internal Revenue Service, rendering written
advice with respect to any entity,
transaction, plan or arrangement, and
representing a client at conferences,
hearings, and meetings.
***
§ 10.33 Best practices for tax advisors.
(a) Best practices. Tax advisors should
provide clients with the highest quality
representation concerning Federal tax issues
by adhering to best practices in providing
advice and in preparing or assisting in the
preparation of a submission to the Internal
Revenue Service. In addition to compliance
with the standards of practice provided
elsewhere in this part, best practices include
the following:
(1) Communicating clearly with the client
regarding the terms of the engagement. For
example, the advisor should determine the
client's expected purpose for and use of the
advice and should have a clear
understanding with the client regarding the
form and scope of the advice or assistance
to be rendered.
(2) Establishing the facts, determining
which facts are relevant, evaluating the
reasonableness of any assumptions or
representations, relating the applicable law
(including potentially applicable judicial
doctrines) to the relevant facts, and arriving
at a conclusion supported by the law and
the facts.
(3) Advising the client regarding the import
of the conclusions reached, including, for
example, whether a taxpayer may avoid

25

accuracy-related penalties under the Internal
Revenue Code if a taxpayer acts in reliance
on the advice.
(4) Acting fairly and with integrity in
practice before the Internal Revenue
Service.
(b) Procedures to ensure best practices for tax
advisors. Tax advisors with responsibility for
overseeing a firm's practice of providing
advice concerning Federal tax issues or of
preparing or assisting in the preparation of
submissions to the Internal Revenue Service
should take reasonable steps to ensure that
the firm's procedures for all members,
associates, and employees are consistent with
the best practices set forth in paragraph (a) of
this section.
§ 10.34 Standards with respect to tax
returns and documents, affidavits and
other papers.
(a) Tax returns.
(1) A practitioner may not willfully,
recklessly,
or
through
gross
incompetence—
***
(ii) Advise a client to take a
position on a tax return or claim
for refund, or prepare a portion of
a tax return or claim for refund
containing a position, that—
(A) Lacks a reasonable basis;
(B) Is an unreasonable position as
described in section 6694(a)(2) of
the Code (including the related
regulations and other published

26

guidance) [i.e., an undisclosed position
without substantial authority, ed.]; or
(C) Is a willful attempt by the
practitioner to understate the
liability for tax or a reckless or
intentional disregard of rules or
regulations by the practitioner as
described in section 6694(b)(2) of
the Code (including the related
regulations and other published
guidance).
(2) A pattern of conduct is a factor that
will be taken into account in determining
whether a practitioner acted willfully,
recklessly, or through gross incompetence.
***
(d) Relying on information furnished by
clients. A practitioner advising a client to take
a position on a tax return, document, affidavit
or other paper submitted to the Internal
Revenue Service, or preparing or signing a tax
return as a preparer, generally may rely in
good faith without verification upon
information furnished by the client. The
practitioner may not, however, ignore the
implications of information furnished to, or
actually known by, the practitioner, and must
make reasonable inquiries if the information
as furnished appears to be incorrect,
inconsistent with an important fact or another
factual assumption, or incomplete.
***
10.36 Procedures to ensure compliance.
(a) Any individual subject to the provisions of
this part who has (or individuals who have or
share) principal authority and responsibility
for overseeing a firm’s practice governed by

27

this part, including the provision of advice
concerning Federal tax matters and
preparation of tax returns, claims for refund,
or other documents for submission to the
Internal Revenue Service, must take
reasonable steps to ensure that the firm has
adequate procedures in effect for all members,
associates, and employees for purposes of
complying with subparts A, B, and C of this
part, as applicable. In the absence of a person
or persons identified by the firm as having the
principal authority and responsibility
described in this paragraph, the Internal
Revenue Service may identify one or more
individuals subject to the provisions of this
part responsible for compliance with the
requirements of this section.
(b) Any such individual who has (or such
individuals who have or share) principal
authority as described in paragraph (a) of this
section will be subject to discipline for failing
to comply with the requirements of this
section if—
(1) The individual through willfulness,
recklessness, or gross incompetence does
not take reasonable steps to ensure that the
firm has adequate procedures to comply
with this part, as applicable, and one or
more individuals who are members of,
associated with, or employed by, the firm
are, or have, engaged in a pattern or
practice, in connection with their practice
with the firm, of failing to comply with this
part, as applicable;
(2) The individual through willfulness,
recklessness, or gross incompetence does
not take reasonable steps to ensure that firm
procedures in effect are properly followed,
and one or more individuals who are

28

members of, associated with, or employed
by, the firm are, or have, engaged in a
pattern or practice, in connection with their
practice with the firm, of failing to comply
with this part, as applicable; or
(3) The individual knows or should know
that one or more individuals who are
members of, associated with, or employed
by, the firm are, or have, engaged in a
pattern or practice, in connection with their
practice with the firm, that does not comply
with this part, as applicable, and the
individual, through willfulness, recklessness,
or gross incompetence fails to take prompt
action to correct the noncompliance.
(c) Effective/applicability date. This section is
applicable beginning June 12, 2014.
§ 10.37 Requirements for written advice.
(a) Requirements.
(1) A practitioner may give written advice
(including by means of electronic
communication) concerning one or more
Federal tax matters subject to the
requirements in paragraph (a)(2) of this
section. Government submissions on
matters of general policy are not considered
written advice on a Federal tax matter for
purposes of this section. Continuing
education presentations provided to an
audience solely for the purpose of
enhancing
practitioners’
professional
knowledge on Federal tax matters are not
considered written advice on a Federal tax
matter for purposes of this section. The
preceding sentence does not apply to
presentations marketing or promoting
transactions.
(2) The practitioner must—

29

(i) Base the written advice on reasonable
factual and legal assumptions (including
assumptions as to future events);
(ii) Reasonably consider all relevant facts
and circumstances that the practitioner
knows or reasonably should know;
(iii) Use reasonable efforts to identify and
ascertain the facts relevant to written
advice on each Federal tax matter;
(iv) Not rely upon representations,
statements, findings, or agreements
(including projections, financial forecasts,
or appraisals) of the taxpayer or any other
person if reliance on them would be
unreasonable;
(v) Relate applicable law and authorities to
facts; and
(vi) Not, in evaluating a Federal tax
matter, take into account the possibility
that a tax return will not be audited or that
a matter will not be raised on audit.
(3) Reliance on representations, statements,
findings, or agreements is unreasonable if
the practitioner knows or reasonably should
know that one or more representations or
assumptions on which any representation is
based are incorrect, incomplete, or
inconsistent.
(b) Reliance on advice of others. A practitioner
may only rely on the advice of another person
if the advice was reasonable and the reliance is
in good faith considering all the facts and
circumstances. Reliance is not reasonable
when—
(1) The practitioner knows or reasonably
should know that the opinion of the other
person should not be relied on;

30

(2) The practitioner knows or reasonably
should know that the other person is not
competent or lacks the necessary
qualifications to provide the advice; or
(3) The practitioner knows or reasonably
should know that the other person has a
conflict of interest in violation of the rules
described in this part.
(c) Standard of review.
(1) In evaluating whether a practitioner
giving written advice concerning one or
more Federal tax matters complied with the
requirements of this section, the
Commissioner, or delegate, will apply a
reasonable
practitioner
standard,
considering all facts and circumstances,
including, but not limited to, the scope of
the engagement and the type and specificity
of the advice sought by the client.
(2) In the case of an opinion the practitioner
knows or has reason to know will be used
or referred to by a person other than the
practitioner (or a person who is a member
of, associated with, or employed by the
practitioner’s firm) in promoting, marketing,
or recommending to one or more taxpayers
a partnership or other entity, investment
plan or arrangement a significant purpose of
which is the avoidance or evasion of any tax
imposed by the Internal Revenue Code, the
Commissioner, or delegate, will apply a
reasonable
practitioner
standard,
considering all facts and circumstances, with
emphasis given to the additional risk caused
by the practitioner’s lack of knowledge of
the taxpayer’s particular circumstances,
when determining whether a practitioner
has failed to comply with this section.

31

(d) Federal tax matter. A Federal tax matter, as
used in this section, is any matter concerning
the application or interpretation of—
(1) A revenue provision as defined in
section 6110(i)(1)(B) of the Internal
Revenue Code;
(2) Any provision of law impacting a
person’s obligations under the internal
revenue laws and regulations, including but
not limited to the person’s liability to pay
tax or obligation to file returns; or
(3) Any other law or regulation administered
by the Internal Revenue Service.
(e) Effective/applicability date. This section is
applicable to written advice rendered after
June 12, 2014.

Notes and Questions
22. Leon is a tax lawyer who regularly e-mails his clients. His clients
appreciate the convenience. Carla has asked Leon to consider the
tax planning possibilities of a particular investment she is
considering, and Leon responds in an e-mail advising her of
various ways the investment can be planned in order to avoid
unnecessary taxes. Is Leon engaged in practice before the IRS? If
so, what are the requirements for the advice he is writing in his email? What if Leon does not e-mail Carla but only explains the
alternatives in a telephone call, is he subject to Circular 230 with
respect to the phone call’s contents?
23. Laura is a tax lawyer. Her client Cody is an impatient business
man, he is always pressing Laura for the “bottom line” and “to
get there without a bunch of lawyer time.” Cody has invested in a
business that has generated a loss this year. Cody’s CPA wants to
avoid the application of the IRC § 469 passive activity loss limit.
In order to do so, Cody’s participation in the activity must have
been “material,” and the CPA is taking the return position that

32

Colby’s participation was material. The CPA has told Cody that
he can be protected from an IRC § 6662 negligence penalty even
if the “material participation” return position is not sustained on
audit or in litigation, so long as he has written advice from a
lawyer. Prompted by his CPA, Cody tells Laura to assume that he
spent more than 500 hours actively engaged in the business. This
is an essential fact, as, if true, it would mean Cody materially
participated and thus is not subject to the passive activity loss
limits. Laura does not know whether Cody spent so much time
with the business. On the one hand, he is a very busy man
involved in many different businesses, but, on the other hand,
she knows he is a very hard worker and it is possible that he did.
Cody has told Laura not to “rack up the legal fees” on this but
just send him a short e-mail advising him of the tax consequences
if the assumption is true. What should Laura do? If she makes the
assumption, she may be violating her duties under Circular 230.
However, if she spends more time on the issue, trying to
document how many hours he spent on the business, she is
violating her client’s instructions (and he will not pay for it!).
Should she undertake the additional work—but simply not
charge Cody for it? Query why the CPA suggested Cody ask
Laura for the analysis and did not provide it herself—after all, the
CPA would earn a fee for the work. (Is the CPA right about so
easily avoiding the negligence penalty? Read Treasury Regulations
§ 1.6664-4(c)).
24. Review the explanation of “substantial authority” in Treasury
Regulations §§ 1.6662-4(d)(2) and (d)(3) (above). Under Circular
230 § 10.34(a)(2), a tax lawyer may not willfully advise a client to
take a position that lacks substantial authority, unless the position
is disclosed to the IRS. As explained above, this is often
characterized as a 40% chance of success on the merits. This is
the minimum standard of confidence required for undisclosed
positions, and it became the requirement in 2011. However, in
1985, the ABA Section of Taxation’s Committee on the
Standards of Tax Practice issued guidelines that tax advice should
have a “realistic possibility” of successful defense in court,

33

meaning a “likelihood of success closely approaching one-third
….”15 Thus, the tax section’s minimum standard is lower than
that of Circular 230. Who regulates the tax bar? Who has the
power to discipline tax lawyers? How much advice is likely to fall
below the “substantial authority” standard while remaining above
the “realistic possibility” standard? Note that, after the changes to
Circular 230, the penalty standard in the Code and the standard in
Circular 230 have been harmonized. Should a tax lawyer ever be
entitled to advise a client to take a position contrary to penalty
standards?
25. While the substantial authority standard might not seem high
compared to the realistic possibility standard, compared to a
standard that legal advice should be merely non-frivolous, the
substantial authority standard seems very high. Advice with even
a 5% chance of success in court may not be frivolous, but the
realistic possibility standard requires about a 33% chance of
success. But, why should a lawyer ever give advice she believes is
more likely than not to fail in court? After all, if the advice has a
40% chance of success, it has a 60% chance of failure. What
percentage of success do you think clients expect to “buy” with
tax advice from a tax lawyer?
26. Liz is a tax lawyer who has met with a potential new client, Chris.
Chris owns several business entities. Chris has not retained Liz.
Rather, after reviewing his information, Liz is going to make a
presentation to Chris and then he will decide whether or not to
hire her. Liz studies the structure of the business entities, and she
discovers that the structure is very tax inefficient. She concludes
that with some straightforward re-structuring she could reduce
the overall tax liabilities of the entities by about $30,000 each
year. The restructuring is very straightforward and Liz is surprised
that Chris has not done it in the past. She believes it is so
straightforward that it will take only about six hours of her time,
which at her standard $500 an hour billing rate is $3000. Liz is
very interested in making a good impression on Chris, hoping to
win his long-term business. She believes she can impress him if
she “guarantees” her work as part of her presentation to him. She

34

is considering offering to charge him a contingent fee of 10% of
the tax savings, which she thinks will be about $3000. Further, if
the IRS successfully challenges the restructuring in the future, she
will refund the fee. Ignoring the complications of reasonably
defining “tax savings,” is this type of fee proper?
27. Circular 230 obligates the lawyer on many issues that are also the
subject of state law, such as conflicts of interest, client
information, and diligence. The Circular 230 requirements and
the state law requirements may not be identical. For example, the
conflict waiver requirements under § 10.29 include time periods
and signatures that may not be found in state bar rules regarding
conflicts of interest. What if the two directly conflict? What if, for
example, information required to be disclosed under § 10.20 is
prohibited from being disclosed by state bar laws? If it is
impossible to comply with both, what is a tax lawyer to do? In
some situations, federal regulations pre-empt state law. Does
Circular 230? (Model Rule 1.6 allows disclosure of confidential
information when necessary to comply with “other law.” Is
Circular 230 “other law”?)
28. Lou is the senior partner in a tax law firm. What are his
responsibilities with respect to the firm’s practices under Circular
230 §§ 10.33 and 10.36? How would Lou educate himself about
what constitutes “best practices?” Recall that Treasury
Regulations § 1.6694-2(e) references office procedures that may
protect tax lawyers from certain penalties.
Circular 230 establishes disciplinary procedures. Those who practice
before the IRS may be reprimanded, suspended, or disbarred.
Circular 230 §§ 10.25–.52. If a practitioner is suspended or disbarred,
no other practitioner may employ or accept assistance from them.
Circular § 10.24. Consider that the agency before which the lawyer
represents clients is the same agency that is authorized to suspend or
disbar him or her from doing so. Is that troubling?
WASHBURN v. SHAPIRO

409 F. Supp. 3 (S.D. Fla. 1976)

35

An accountant was criminally convicted under § 7206(a)(2) (he
knowingly prepared a joint return for a client who signed on behalf
of his wife even though he was not authorized to do so). As a result
of his criminal conviction, the Director of Practice instituted
disbarment proceedings. An administrative law judge held that the
accountant had violated Circular 230 § 10.50 (he had behaved
disreputably), and he disbarred the accountant from practice before
the IRS. The accountant appealed to the General Counsel of the
Treasury Department, who affirmed the administrative law judge’s
decision. The judicial review of this final decision, of an
administrative agency, is “whether there is substantial evidence in the
record to support the challenged administrative determination,” and
the court found there was. The accountant was convicted of a felony
and did not deny it, and under Circular 230 the conviction subjected
him to disbarment. The accountant complained that his rights to due
process had been violated, but, upon reviewing various steps in the
process, the court concluded he received “the requisites of
elementary fairness–due notice and the opportunity to be heard” to
which he was entitled.

2.3. Regulating Tax Lawyering through Malpractice
Standards
Lawyers may be sued by unhappy former clients and, in some cases,
persons who may not have been clients—or who, at least, the lawyer
did not consider to be a client. Most commonly those suits are
premised on the lawyer’s negligence or violation of fiduciary duties to
the client (or non-client third parties) or contractual duties between
the lawyer and client. Lawyering with an eye on a successful defense
of professional judgment can consume the mental and emotional
energy of lawyers on a regular basis. Limiting liability, especially for
the acts of those with whom one works, is an ongoing concern of
lawyers. Many lawyers carry malpractice insurance, which means that
complying with the terms of the policy becomes important. Worrying
about malpractice suits and the consequent strategies for reducing
risk may do far more to regulate lawyering than fear of discipline by
the state bar and, for tax lawyers, the Treasury Department.

36

In a malpractice suit, lawyers are liable for failing to “exercise
the competence and diligence normally exercised by lawyers in similar
circumstances.”16 Both competence and diligence also are required
under Model Rules 1.1 and 1.3 and Circular 230 §§ 10.22 and 10.35.
Of course, the difference is that a malpractice suit may result in a
financial judgment against the lawyer, while violating the ethics rules
may result in disciplinary actions. Generally, in terms of damages, tax
lawyers may find themselves liable for the penalties and interest their
clients had to pay the IRS for the improper tax position, but usually
not the increased tax liability itself.

Notes and Questions
29. Carl is involved in a real estate transaction that could easily have
been structured to qualify for non-recognition under IRC § 1031.
However, his lawyer, Lee, failed to advise him of this possibility.
The result is an immediate $400,000 tax liability that otherwise
might have been deferred indefinitely. What if Lee thought Carl
had a CPA providing him tax advice? What if Lee had written a
letter to Carl stating that he would not be responsible for tax
advice? What if a provision to that effect was in Lee’s
engagement agreement with Carl? Is it ethically appropriate for
Lee to attempt to transfer the burden of the tax advice to a CPA?
Would it make a difference if he attempted to transfer it to
another lawyer? Could he be disciplined by the state bar for
attempting to do this? Would this be a reasonable limit on his
scope of representation? (Read Model Rule 1.2(c).) If you were
representing Carl in a malpractice suit, what would you argue the
damages should be based on? If you were defending Lee, what
would you argue about the right measurement of damages?
30. Lara is a lawyer who has been practicing for a year. She is a solo
practitioner. She has no experience in handling tax matters. She is
handling her first divorce case and she is concerned that there
may be tax issues. She wants to involve a specialist. Her law
school classmate, Ted, is a first year lawyer interested in handling
tax matters. She also knows Terry who is a very experienced tax
lawyer. Lara’s client is of very modest means and the total

37

property involved is of relatively little value. Lara could refer her
client to either Ted or Terry. Ted, as a new lawyer, charges a
much lower fee than Terry. In fact, it seems unlikely that her
client could afford Terry’s fees. Lara also knows an experienced
CPA who would be willing to “help” Lara with the tax issues but
not take primary responsibility. The CPA’s rates are much lower.
What should Lara do? What if she refers the client to Ted,
knowing Ted is not very experienced, would she be liable for
Ted’s mistakes? What if, as a practical matter, the client cannot
afford the tax expertise she needs—but Lara is representing her?
31. Leo is not a tax lawyer. When tax issues arise, he routinely
provides his clients with the names of three tax specialists,
suggesting they interview each of them. He does this in an effort
to protect himself from claims by disgruntled former clients that
he should be liable for the bad advice of the lawyer to whom he
referred them. If a tax issue arises that is so unusual and technical
that only one of those tax lawyers is competent, how should Leo
handle the referral? Since Leo is not a tax lawyer, how would he
recognize that the issue is so unusual and technical that only one
of those lawyers is competent? On a more basic level, how does
Leo spot all the tax issues that need referral when he is not a tax
lawyer?
32. Model Rules 1.1 requires a lawyer to provide “competent
representation.” The comments explain that a “lawyer can
provide adequate representation in a wholly novel field through
necessary study.” Is that really true? What are the risks of taking a
client with the plan of engaging in “necessary study” in order to
competently represent the client?
33. Both lawyers and CPAs practice in the tax field. How do you
think assessment of malpractice risks affect the division of the
field between the two professions?

38

3. Ethical Problems for Tax
Lawyers
While tax lawyers face many of the professional responsibility
problems other lawyers do, such as conflicts of interest and handling
confidential information, there are several distinctive situations that
pose ethical problems for tax lawyers. First are those situations in
which a tax lawyer provides advice to a client in a manner expected
to protect the client from certain penalties, even if the advice turns
out to be wrong. Second are situations involving mistakes, such as
discovering that a prior year’s tax return is incorrect or catching the
IRS making a mistake in the client’s favor. Finally are situations that
involve how private tax lawyers interact with lawyers and other
employees at the IRS.

3.1. Tax Opinions and Tax Shelters
A taxpayer who makes an “honest mistake” still owes the taxes due
(and interest on the amount due), an audit may reveal this. Yet, the
taxpayer must pay additional penalties only in certain situations. For
example, IRC § 6662 imposes a 20% penalty, if the taxpayer
underpaid tax due to “negligence or disregard of the rules or
regulations,” or, regardless of negligence or disregard, if the
underpayment was “substantial” (i.e., more than the greater of $5,000
or 10% of the tax owed). IRC § 6662(b)(1), (b)(2), (d)(1). 17 It is in
seeking protection from penalties that many clients turn to tax
lawyers. Thus, clients will often seek assurances from a tax lawyer as
to a favorable position on the return since such assurances may
protect them from the penalties, even if the position fails to be
sustained on audit or in litigation. Tax lawyers earn significant fees in
providing such assurances (i.e., providing opinions as to the proper
tax treatment).
In general, a taxpayer will not be subject to a § 6662 penalty if she
acted reasonably and in good faith with respect to the return position
that resulted in the underpayment of tax. IRC § 6664(c)(1). A
taxpayer who relies on a tax lawyer’s professional advice may cite

doing so as evidence of acting reasonably and in good faith. Treasury
Regulations § 1.6664-4(b)(1). However, the taxpayer must have
disclosed all relevant facts to the lawyer, and the lawyer must base the
advice on all relevant law taking the facts into consideration, making
no unreasonable assumptions. Treasury Regulations § 1.6664-4(b)(1).
In short, the tax lawyer’s advice must be reasonable and in good faith
and the taxpayer’s reliance itself must be reasonable and in good
faith.
While the taxpayer penalty regime is complex, it is important to note
that there are specific protections provided for different levels of
confidence in tax advice. Similar to the requirements on a tax return
preparer under § 6694, there will be no penalty premised on a tax
position for which there is “substantial authority” or a tax position
that is disclosed on Form 8275 and for which there is a “reasonable
basis.” IRC § 6662(d)(2)(B). Re-read the considerations described
above with respect to § 6694 and the meaning of “substantial
authority” and “reasonable basis.” Remember that a position with
substantial authority is one for which there is about a 40% chance of
success, if litigated, and a position for which there is a reasonable
basis is one for which there is about a 10–20% chance of success if
litigated.
The substantial authority and reasonable basis standards are objective
standards. However, in some instances, in order to avoid a penalty,
the taxpayer must also reasonably believe that the position is “more
likely than not” to be sustained on its merits in litigation. 18 The “more
likely than not” standard is greater than 50%. A taxpayer is
considered to “reasonably believe” if the taxpayer reasonably relies in
good faith on the opinion of a professional tax advisor, if the opinion
is based on the tax advisor’s analysis of the pertinent facts and
authorities … and unambiguously states that the tax advisor
concludes that there is a greater than 50-percent likelihood that the
tax treatment of the item will be upheld if challenged by the Internal
Revenue Service. Treasury Regulations §§ 1.6662-4(g)(4)(i)(B) [noncorporate taxpayer]; 1.6664-4(f)(2)(B)(2) [corporate taxpayer].
This special requirement applies to “tax shelters.” In common usage,
a “tax shelter” is a complicated tax scheme intended to generate

40

substantial tax benefits that do not correspond to the underlying
economic realities of the scheme. In other words, it is a complicated
and abusive tax plan. Tax shelters tend to be marketed as
investments, and those who are marketing the shelters hire tax
lawyers to provide written tax opinions designed to protect the
investors from penalties. 19 Thus, these opinions are extremely
valuable to tax shelter promoters—and providing these opinions on
law firm letterhead can be an extremely lucrative business for tax
lawyers. Over a five year period, one large firm tax partner
“personally netted $93 million”—and hundreds of millions for his
firm—by providing about six hundred tax shelter opinions. 20
However, when the tax shelters began to unravel under IRS scrutiny,
the lawyer and his firm were sued in a class action suit brought by the
tax shelter investors, which resulted in the dissolution of the law firm,
payments to the investors, and criminal penalties. 21
The war against tax shelters began in the 1970s. 22 With income tax
rates exceeding 70%, many high earning individual taxpayers were
investing in tax shelters. These shelters had no economic reality—and
often no other reality—but supposedly generated great tax
deductions that could be used to offset (i.e., “shelter”) other income.
By 1980, the IRS began to focus on written opinions given by tax
advisors. These opinions were given to protect investors from
penalties, even if the underlying tax benefits were ultimately
disallowed. Given the significant tax “savings” of these shelters and
the time value of money, even if the investors had to pay the taxes at
some point, the shelter could remain a good “investment,” so long as
there were no penalties imposed. The IRS focused on four types of
problematic opinions: (1) substantively incompetent opinions; (2)
opinions based only on assumed facts; (3) opinions that discussed the
law and the facts but never related the two; and (4) negative opinions,
those that said there was a reasonable basis but that it was more likely
than not the position would not be sustained. In 1982, Congress
amended the substantive law regarding tax penalties, making these
problematic opinions useless for penalty protection. In that same
year, the American Bar Association Committee on Professional
Responsibility issued guidance requiring tax lawyers writing opinions

41

to make factual inquiries and relate the law to the facts. In the
context of the new penalty law, Circular230 was amended in 1984to
include a new § 10.33 on tax shelter opinions, which essentially
mirrored the ABA guidance. This was the first time that tax advice as
such was covered by Circular 230.
About twenty years later, tax shelters had become increasingly
sophisticated and oriented towards corporate taxpayers. Congress
amended the law to explicitly sanction the regulation of written tax
advice by the IRS and the IRS was encouraged to expand its efforts
against tax shelter opinions. The result was a new Circular 230 §
10.35. The purpose of Circular 230 § 10.35 was to make it more
difficult for taxpayers to evade penalties by claiming good faith
reliance on tax opinions. This was done by forcing tax professionals
to write those opinions in a very detailed way. Each relevant fact had
to be identified and related to the relevant law. In short, all was to be
made explicit, nothing left implicit or assumed or ignored. The
professional had to give a more likely than not opinion on every
significant tax issue. If the professional wasn’t willing to do that, then
the opinion had to inform the taxpayer that it wouldn’t provide
penalty protection.
Many tax lawyers became concerned that Circular 230 § 10.35 did not
apply only to tax shelters, but also might be applied to less
controversial tax avoidance techniques. Considerable anxiety
developed in the tax bar as to giving written advice, and the IRS did
nothing to lessen the anxiety. The only way to avoid having to
provide a detailed written opinion that complied with covered
opinion rules was to include a disclaimer on written advice that it did
not provide penalty protection. The result was the near-universal use
of such disclaimers on lawyer e-mails and other communications.
However, within a decade, it became generally agreed that the effect
of Circular 230 § 10.35 was not so much to increase the quality of tax
advice as it was to increase the amount of boilerplate disclaimers. In
2014, the opinion rules were removed from Circular 230, leaving
written advice to be governed by § 10.37, which required nothing in
particular other than reasonableness.

42

Notes and Questions
34. “Tax shelters” are commonly thought of as abusive transactions.
However, the technical definition of a tax shelter includes “any
plan or arrangement, if a significant purpose of such … plan or
arrangement is the avoidance … of Federal income tax.” IRC §
6662(d)(2)(C). While the organized tax bar disapproves of tax
lawyers engaged in abusive planning, this definition of “tax
shelter” has troubled many tax lawyers because it technically
seems to include legitimate tax planning. How might “tax shelter”
be re-defined so that it included only abusive transactions?
35. It may be that criminal prosecution of tax advisors becomes the
“weapon of choice” for deterring abusive tax scheming. 23 Given
that professional ethics standards have failed, is criminal
prosecution the only alternative left?

3.2. Mistakes
To err is human. But there are many kinds of errors, and when the
errors involve the administration of the tax law, the tax lawyer may
find herself pondering what to do. For example, tax lawyers routinely
ponder what to do when they discover mistakes in a prior year’s
return.
Circular 230 § 10.21 provides as follows:
A practitioner who, having been retained by a
client with respect to a matter administered by
the Internal Revenue Service, knows that the
client has not complied with the revenue laws
of the United States or has made an error in
or omission from any return, document,
affidavit, or other paper which the client
submitted or executed under the revenue laws
of the United States, must advise the client
promptly of the fact of such noncompliance,
error, or omission. The practitioner must
advise the client of the consequences as

43

provided under the Code and regulations of
such noncompliance, error, or omission.
Circular 230 makes it clear that a tax lawyer has the obligation to
advise the client of any “noncompliance, error, or omission.” If a tax
lawyer discovers a mistake on a prior year’s return, it is clear that the
tax lawyer should inform the client of the mistake. Note that there is
no requirement that the client be advised to file an amended return,
but Circular 230 requires the client be advised of the “consequences”
of the mistake. What are the consequences?
It is often said that there is no legal obligation to file an amended tax
return correcting a prior year’s return. Some, however, argue that
because the tax is legally due and owing, the taxpayer is legally
obligated to correct the prior return and pay the tax due. 24 In other
words, the argument is that, even if the IRC does not require an
amended return, other legal principles do. Others may point to
language in the Treasury Regulations that provide that taxpayers
“should” file an amended return, but it is hard to miss that the
regulations do not use the word “must” or “shall.” See Treasury
Regulations §§ 1.45-1(a) and 1.461-1(a)(3). The IRS certainly
encourages the filing of amended returns; it provides forms for that
purpose. Even if filing an amended return is not required by the IRC,
filing the return and paying the tax due may be useful for other
reasons, such as stopping the accrual of interest—after all, the tax
due may be discovered on an audit, even if no amended return is
filed.
What if the mistake on the prior year’s return was not an “honest
mistake,” but intentional? Choosing to amend the return may be the
choice to disclose a crime and Fifth Amendment rights may be
implicated. If a taxpayer has the right not to incriminate himself,
obviously his lawyer is not obligated to advise him to do so.
Tax returns are filed on an annual basis, but a given return may be
relevant across many years. If the client chooses not to amend the
return to correct one year’s mistake, the tax lawyer cannot simply
ignore her knowledge of the mistake in continuing to represent the
client. She must be diligent in ensuring that she does not incorporate

44

the mistake into future planning or reporting. Review Circular 230 §
10.22; Model Rules 1.2, 1.6, 4.1 and 8.4; IRC §§ 6701 and 7206(2).
This may be very difficult in some situations, but not others. In some
situations, the most prudent course of action may be withdrawing
from the representation (and the client should be advised that
withdrawal may be one of the “consequences” implicated by § 10.21.)
Of course, as a client’s circumstances and tax planning changes, and
as the tax law changes, tax positions in prior years may suddenly
become more important in later years than anyone would have
anticipated.
If the client chooses not to correct the return and the return later
becomes the subject of an audit, the tax lawyer’s bind increases and
she may need to withdraw. While the return is being reviewed, it may
be almost impossible for the lawyer not to make a false or misleading
statement about the return, and, of course, she is also generally
unable to disclose the error over the objection of the client. Review
Circular 230 § 10.22; Model Rules 1.2, 1.6, 4.1, and 8.4.
What if the mistake in question was not made by the client on a prior
year’s return but rather by the IRS—and it is a mistake in your
client’s favor? The Committee on Standards of Tax Practice of the
ABA Tax Section considered this issue in detail in its Standards of
Tax Practice 1999-1. The Committee distinguished between
computational and conceptual mistakes, generally advising that the
tax lawyer notify the IRS of the mistake if it is computational (i.e., a
math mistake) but not if it is conceptual. The Committee considered
that, on the one hand, the lawyer may not disclose confidential
information without the client’s consent (Model Rule 1.6(a)) but, on
the other hand, the lawyer may not engage in dishonest conduct
(Model Rule 8.4(c)). If the client objects to disclosing the IRS’s
computational mistake to it, the tax lawyer may have the duty to
withdraw.

Notes and Questions
36. ABA Formal Opinion 314 instructs the lawyer who knows of a
mistake on a prior return to advise the client to file an amended
return. However, Circular 230 only requires advising the client as

45

to the consequences of failing to correct the mistake. Presumably
bar authorities in states that have adopted the Model Rules would
consult the ABA Formal Opinions in considering discipline
under the rules. Such opinions serve as persuasive authority along
with state ethics opinions. But wouldn’t those authorities be likely
to consult Circular 230 too?
37. Lanny is a tax lawyer who has been hired by a new client. In
reviewing the client’s files in order to provide some tax advice for
a possible business deal, Lanny reviews a prior year’s tax return in
detail. During this review, he discovers a minor mistake that
resulted in very limited tax savings and is extremely unlikely to be
relevant in any future years. Lanny believes the mistake was
“honest,” and that no negligence or other penalty would be
applicable. He believes the client has no legal obligation to amend
the return. The client’s CPA prepared the return. Lanny is
surprised to discover any mistake on a return prepared by this
CPA, as she is well-known for her extraordinary work. Lanny is
concerned that if he tells the client of the mistake, the client may
fire the CPA. Lanny believes the client is very hot-tempered and
fairly unsophisticated and is unlikely to comprehend that hiring a
new CPA will not ensure mistake-free returns in the future. It will
also involve a great deal of transition costs as the new CPA
would have to spend a good deal of time learning about the
client’s business and reviewing the files. Lanny believes it is in the
client’s best interests to retain this CPA. Must Lanny tell the
client about the mistake? What if Lanny believes the error was
not a “mistake” but intentional? What if Lanny had prepared the
return, and then later discovered the error?

3.3. Working with IRS Lawyers and Other Employees
Who would want to be an IRS lawyer? It is a complicated role with
considerable regulation. There are, of course, the state ethics rules,
but there is also Circular 230, tax code provisions (such as IRC §§
6103 and 7214), and the general restrictions on all federal
government lawyers and employees. As with all government lawyers
there are inter-agency issues, intra-agency issues, and bureaucratic

46

realities. There is also the fact that IRS employees, in general, and
IRS lawyers in particular, are rarely well-received. Mentioning at a
dinner party that one is a tax lawyer may chill conversation, but
saying that one is a lawyer for the IRS may have even more dire social
consequences. Violence against IRS employees in general is also a
real risk; more than 900 threats against IRS employees are
investigated each year. 25
Yet many tax lawyers choose to work for the IRS. Working for the
federal government has its benefits in terms of lifestyle, even if not in
terms of cash compensation. But many tax lawyers who choose this
line do it for other reasons. Though not as prevalent a professional
development choice as it once was, service in the IRS may be good
professional training for future private tax lawyers, perhaps much like
a stint in the prosecutor’s office serves future defense attorneys. One
reason some tax lawyers choose the IRS is in order to defend the
interests of the honest taxpayers. These lawyers often think of
themselves not as representing “the system” but “all the taxpayers.”
When litigating against a taxpayer who crossed the line, these lawyers
consider themselves to be representing all of the taxpayers who did
not cross the line.
When private tax lawyers believe their clients did not cross the line in
tax planning and their clients’ reputations and assets are on the line,
they too, of course, consider themselves to be carrying on a noble
crusade. The conflict between the private tax lawyer and the IRS tax
lawyer may occur in an emotional and stressful situation for the
client. It is here that professional rules are essential for navigating the
high stakes and high stresses that otherwise might erode the
professional barriers and reduce the conflict to a personal level.
These situations may also involve another source of tension—
potential sanctions against the tax lawyer. Review the readings above
related to “substantial authority” and “reasonable basis” and the
penalties to which tax lawyers may be subject to as a result of their
tax advice (IRC § 6694), as well as the materials above related to the
criminal sanctions that may be imposed on tax lawyers in certain
situations (IRC § 7206). The tax lawyer may be personally at risk as a
result of a review of the client’s tax reporting, and thus the tax lawyer

47

may be defending not only his client but himself. Indeed, it is often
prudent, and in some situations necessary, for the tax lawyer who
provided the tax planning advice not to be the tax lawyer who
defends it.
With these tensions in mind, consider the following from Circular
230:
§ 10.51 Incompetence and disreputable conduct.
(a) Incompetence and disreputable conduct.
Incompetence and disreputable conduct for
which a practitioner may be sanctioned under
§ 10.50 includes, but is not limited to—
***
(4) Giving false or misleading information,
or participating in any way in the giving of
false or misleading information to the
Department of the Treasury or any officer
or employee thereof . . . knowing the
information to be false or misleading. Facts
or other matters contained in testimony,
Federal tax returns, financial statements,
applications for enrollment, affidavits,
declarations, and any other document or
statement, written or oral, are included in
the term “information.”
***
(7)
Willfully
assisting,
counseling,
encouraging a client or prospective client in
violating, or suggesting to a client or
prospective client to violate, any Federal tax
law, or knowingly counseling or suggesting
to a client or prospective client an illegal
plan to evade Federal taxes or payment
thereof.
***
(9) Directly or indirectly attempting to
influence, or offering or agreeing to attempt

48

to influence, the official action of any
officer or employee of the Internal Revenue
Service by the use of threats, false
accusations, duress or coercion, by the offer
of any special inducement or promise of an
advantage, or by the bestowing of any gift,
favor or thing of value.
***
(12) Contemptuous conduct in connection
with practice before the Internal Revenue
Service, including the use of abusive
language, making false accusations or
statements, knowing them to be false or
circulating or publishing malicious or
libelous matter.
(13) Giving a false opinion, knowingly,
recklessly, or through gross incompetence,
including an opinion which is intentionally
or recklessly misleading, or engaging in a
pattern of providing incompetent opinions
on questions arising under the Federal tax
laws. …

Internal Revenue Manual 4.1.1.7.6.1 - Badges of
Practitioner Abuse (05-20-2005)
(1) Practitioners may be subject to discipline
under Circular 230 if they exhibit a pattern of
attempting to influence the case disposition or
a Service employee to obtain the desired
results in several collection investigations by:
 Using abusive language
 Threatening claims of misconduct (e.g.
Section 1203)
 Making false claims of misconduct
 Making false accusations
 Verbal/Physical threats or assaults

49

 Making a bribe (e.g. offering gifts or other
things of value)
***
(2) A second badge of practitioner
misconduct is a pattern of delay by the
practitioner in performing one or more of the
following actions (Circular No. 230 Section
10.20) during the course of several collection
cases:
 Missing appointments
 Canceling appointments at the last
moment with no good cause provided
 Agreeing
to
provide
requested
documentation and/or information and
then refusing to do so, thereby hindering
the Service's efforts to continue its
investigation
 Providing partial information requiring
repeated call backs and correspondence
causing delays

From 1991-2 C.B. 1137:
A practitioner's meeting with IRS representatives concerning a
client's affairs deteriorated into acrimony. As people began to leave
the meeting room, the practitioner grasped a revenue officer by the
shoulder and urged her to continue the meeting. The revenue officer
refused, telling the practitioner to remove his hand. The practitioner
again grasped the revenue officer by the shoulder and repeated his
request, which was refused.
The matter was referred to the Director of Practice. The Director
notified the practitioner of his possible violation of Treasury
Department Circular No. 230, section 10.51(i), which states that a
practitioner may be discharged or suspended for contemptuous
conduct in connection with practice before the IRS.

50

The physical contact, the Director found, was akin to contemptuous
conduct as defined in section 10.51(i). The practitioner consented to
a short suspension from practice before the IRS. The Director
deemed suspension appropriate due to the seriousness of physically
accosting an IRS employee engaged in the performance of his duties.
However, the Director's finding that the practitioner made no
attempt to threaten or coerce was a mitigating circumstance.

Notes and Questions
38. If a tax lawyer is disciplined under Circular 230, how likely is it
she will also be disciplined by state bar authorities? What is the
difference?
39. IRS lawyers may be motivated by the idea that they represent “all
the (other) taxpayers.” But, of course, this is an insufficient
conception of their client’s identity. It is important for a lawyer to
know who the client is, for example, in order to determine with
whom confidential information may be shared. If Leo is an IRS
lawyer, who is his client? The U.S. government? The President?
The Treasury Department? The IRS? The Secretary of the
Treasury? The Commissioner of the IRS? If Leo is asked by
Congress to provide certain information, may he? Must he? In
what circumstances? What if the President requests it? What if
the IRS Commissioner requests it? Lawyering for the government
raises complex professional responsibility issues.
40. If an IRS lawyer concludes that the taxpayer’s argument is very
strong and the government’s argument is very weak, may she
continue to pursue the taxpayer? What if she concludes the law is
squarely on the taxpayer’s side rather than the government’s side?
What if the government’s position is not frivolous, but close to
it? In Rev. Proc. 64-22, 1964-1 C.B. 689, the IRS announces that
it will not assert a “strained construction” of the law. What does
that mean?
41. Lacey is a tax lawyer. She is representing Cory before the IRS.
Lacey discusses the return with both Cory and the CPA who
prepared the return. One of the transactions reflected on Cory’s
return relates to the sale of real property to Cory’s sister-in-law in

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exchange for a promissory note. Lacy learns that, initially, the
transaction “was not documented exactly right,” as the CPA put
it. But, after first being contacted by the IRS, the CPA advised
Cory to contact a lawyer, Abe, who “fixed the problem” by
providing documentation back-dated to the date of sale and
containing the terms the CPA advised should be contained in
order to qualify for the position taken on the return. The CPA
has provided Lacy with an envelope of supporting documents,
most of which are not related to this transaction but rather were
specifically requested by the IRS. If Lacy simply forwards the
envelope to the IRS with a cover letter stating only “enclosed
please find the requested materials,” is she subject to discipline?
Has she committed mail fraud? Has she committed any other
crime?
42. Larry is a tax lawyer. He is representing Casey before the IRS.
The IRS employee has asked Larry for copies of a sales contract,
the minutes of a corporation Casey owns, and a lease agreement.
Larry agrees to send these documents during the first week of
July. When he fails to do so, the IRS employee calls and asks him
for the information. He sends the sales contract in the last week
of July. He then sends several pages of the lease agreement in
mid-August, and then, two weeks later, after receiving another
call from the IRS employee, he sends the remainder of the lease
agreement with a cover letter apologizing for failing to send the
entire agreement earlier. In September he sends the corporation’s
minutes for its annual meeting, and then in October, after the
IRS employee calls to ask if there are other minutes, Larry
provides the minutes for the corporation’s special meetings. Is
this misconduct? Does it matter if Larry is intending to delay the
matter, or if, instead, he is simply disorganized?

1

31 U.S.C. § 330 (2012?).

2

Circular 230 § 10.34.

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Donald B. Tobin, Richard Lavoie, and Richard E. Trogolo, Problems in
Tax Ethics 22 (2009). See Jasper L. Cummings, Jr., The Range of Legal Tax
Opinions, with Emphasis on the ‘Should’ Opinion, Tax Notes, February 17,
2003, p. 1125, 1128.
3

Tax lawyers are said to have a “duty to the system.” Bernard Wolfman,
James P. Holden, and Kenneth L. Harris, Standards of Tax Practice § 101.2
(5th ed., 1999). Professor Deborah Schenk has written that the selfreporting nature of the tax system means that the tax system cannot permit
the “absolute adversarial” relationship that lawyers might have in other
situations. Deborah H. Schenk, Book Review: Tax Ethics, 95 Harv. L. Rev.
1995, 2004 (1982). The idea that “tax ethics … must be approached from a
special perspective”, as a consequence of the self-reporting nature of our
tax system, seems the most common argument for tax lawyers’ duty to the
system. Id. at 89. See also Anthony C. Infanti, Eyes Wide Shut: Surveying
Erosion in the Professional Tax Bar, 22 Va. Tax. Rev. 589, 606 (2003).
However, some have criticized this conception of the tax lawyer. See, e.g.,
David J. Moraine, Loyalty Divided: Duties to Clients and Duties to
Others—the Civil Liability of Tax Attorneys Made Possible by the
Acceptance of a Duty to the System, 63 Tax Law. 169 (2009).
4

See, e.g., Treasury Regulations § 1.6662-4(d)(2) (“The possibility that a
return will not be audited, or, if audited, that an item will not be raised on
audit, is not relevant in determining whether the substantial authority
standard (or the reasonable basis standard) is satisfied.”)
5

6

5 U.S.C. § 500 (2012?).

Indeed, under Circular 230 §10.3(c), enrolled agents may also practice
before the IRS, but this discussion is limited to tax lawyers and CPAs as
these two professions dominate tax planning.
7

National Conference of Lawyers and Certified Public Accountants: A
Study of Interprofessional Relationships, 36 Tax Law. 26, 28–29 (1981).
8

9

Id. at 33–34.

10

Id. at 34.

11

Id. at 34–35.

12

Id. at 35.

Donald B. Tobin, Richard Lavoie, and Richard E. Trogolo, Problems in
Tax Ethics 22 (2009). See Jasper L. Cummings, Jr., The Range of Legal Tax
13

53

Opinions, with Emphasis on the ‘Should’ Opinion, Tax Notes, February 17,
2003, p. 1125, 1128.
Donald B. Tobin, supra, note 11, at 25 Cummings, supra, note 11, 1126–
27.
14

Report of the Special Task Force on Formal Opinion 85-352, 39 Tax
Law. 635, 639-40(1985). The realistic possibility standard does not need to
be met if the position “is advanced by payment of the tax and claim for
refund, which necessarily sets forth in detail each ground upon which a
refund is claimed.” ABA Tax Section’s Report of the Special Task Force on
Formal Opinion 85-352, 39 Tax Law. 635, 639 (1985). See also IRC
§6694(a)(2)(B) and IRC § 6692(d)(2)(B). Note that pursuit-of-refund
alternative would only be available for taxpayers with sufficient funds to pay
the tax upfront and then pursue the refund. This connects with the forumshopping issues between the Tax Court and the federal district
courts/Court of Federal Claims.
15

Restatement (Third) of Law Governing Lawyers § 52 (The Standard of
Care).
16

Additionally, the penalty applies to substantial valuation misstatements.
IRC § 6662(b)(3).
17

If the tax lawyer is considered a preparer (as discussed above), a position
related to a tax shelter or reportable transaction will be considered
unreasonable, unless it was reasonable for the lawyer to believe that the
position was “more likely than not to be sustained on its merits” in
litigation. IRC § 6694(a)(2)(C).
18

The opinions, of course, do not protect the investors from paying any
back taxes (and interest) due when the scheme is audited, but are intended
to protect the investors from penalties.
19

Karen C. Burke and Grayson M.P. Crouch, COBRA Strikes Back:
Anatomy of a Tax Shelter, 62 Tax Law 59, 61-62 (2008).
20

21

Id. at 63.

See Michael Hatfield, Committee Opinions and Treasury Regulation: Tax
Lawyer Ethics, 1965-1985, 15 Fla. Tax Rev. 675–735 (2014).
22

See Scott A. Schumacher, Magnifying Deterrence by Prosecuting
Professionals, 89 Ind. L.J. 511–58 (2014).
23

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It is assumed that a mistaken past return resulting in an overpayment will
be corrected in order to claim a refund.
24

Andrea Ball, Hatred Toward IRS Nothing New, The Dallas Morning
News, March 3, 2010,
http://www.dallasnews.com/sharedcontent/dws/news/texassouthwest/
stories/DN-irsworkers_03tex.ART.State.Edition1.4bdd764.html.
25

55