By Rick Yandle, Esq., CPA — federal criminal & civil tax defense
An extension gives you six more months to file a return. It gives you no more time to pay, and it is no defense to a charge of failing to file. Request one every year and never file, and the extensions can become evidence, year after year, that you knew a return was due. A Connecticut attorney's sentencing last month shows how that plays out.
What happened
On September 14, 2026, a federal judge in Bridgeport sentenced Michael Simes, an attorney from Newtown, Connecticut, to 10 months in prison and a year of supervised release. According to the U.S. Attorney's announcement, Simes did not file returns for 2013 or for 2016 through 2022. He had more than $5.6 million of gross income in those years, and the tax loss came to $1,876,307. For 2016 through 2020 he requested extensions to October of each year, and then filed nothing.
For 2012, 2014, and 2015 he did file, but paid only a fraction of the tax his own returns reported. He pleaded guilty in March to three counts of failure to file. The court ordered restitution of $2,871,676, the presently outstanding balance, and he reports to prison on January 20, 2027.
A misdemeanor, and a simple one to prove
Section 7203 makes it a misdemeanor to willfully fail to file a required return. The government proves three things: the person was required to file, he did not file when the law required, and the failure was willful. Each count carries up to a year in prison.
Willfulness is the only element with any room in it, and the Supreme Court defines it narrowly: a voluntary, intentional violation of a known legal duty (Cheek v. United States, 498 U.S. 192 (1991)). The government does not have to prove a motive to evade, and it does not have to prove the taxpayer hid anything. It has to prove he knew.
That is where the extensions do their damage. Form 4868 asks for an estimate of the tax owed. A taxpayer who requests one is telling the IRS that he knows a return is due and roughly what it will show. The Justice Department's Criminal Tax Manual lists the facts from which willfulness is usually inferred, including failing to file for several years and having filed in earlier years. Five years of extension requests, next to returns filed for 2012, 2014, and 2015, left little room to argue he didn't know a return was due. Knowledge alone does not make the failure willful, but it is the core of the government's proof.
An extension also moves the deadline. Once it is granted, the return is due on the extended date, so the offense is complete in October rather than April. Interest and the failure-to-pay penalty, meanwhile, run from April 15 regardless.
Eight years, three counts
Each year a required return goes unfiled is a separate offense, which gives a prosecutor a menu. Simes had eight unfiled years and pleaded to three. The announcement does not say which three, but some years were never on the menu. The limitations period for failure to file is six years (Section 6531(4)), and 2013 was well past it by the time of the plea.
The uncharged years still count. At sentencing, tax loss is measured across the whole course of conduct, not count by count (U.S.S.G. Section 2T1.1, comment. (n.2)), and the restitution order here reached well past the counts of conviction. A misdemeanor plea caps the prison exposure at a year per count. The money is a separate question.
Why the prosecuted non-filers tend to be professionals
Millions of people fall behind on filing, and very few are prosecuted. Most nonfiler enforcement is notices. In an August 2026 report (No. 2026-308-047), the Treasury Inspector General for Tax Administration found that 38,824 high-priority nonfiler cases from the IRS's high-income nonfiler initiative had sat in first-notice status for more than a year, with about $15.7 billion in potential assessments. The IRS moved them forward in March 2026.
The cases that go criminal share a profile, and Simes fits it:
- High income over several years, so the tax loss is large enough to justify a prosecution.
- A professional whose education and work make an "I didn't know" defense hard to put to a jury. An attorney who files extensions is hard to cast as confused about the filing requirement.
- A paper trail the taxpayer made himself: extensions, earlier returns, and information returns from clients and payers.
- Deterrence value. A prosecuted lawyer, doctor, or CPA reaches the rest of that profession in a way an ordinary case does not.
For a licensed professional, the criminal case is also rarely the last proceeding. A conviction often has to be reported to the licensing authority, and a disciplinary matter tends to follow.
The years he did file
The filed-but-unpaid years are the part of the story easiest to miss. A return filed with a balance due is assessed when it is processed, and collection starts on its own: notices, failure-to-pay penalties, and, for balances of this size, a likely revenue officer. By the time Simes stopped filing, the IRS already had his name, his income, and three years of unpaid balances. A prosecutor can present the unfiled years against that background as a choice made with eyes open.
Failing to pay a reported balance can itself be charged under Section 7203, though it rarely is on its own. Moving or hiding money while the IRS is trying to collect is a different and more serious case: that is the affirmative-act line between this misdemeanor and felony evasion, covered in When "I Can't Pay" Becomes a Crime.
Restitution reaches the whole balance
The restitution figure, $2,871,676, is larger than the $1,876,307 tax loss on all eight unfiled years combined. It was set at the presently outstanding balance, which carries penalties, interest, and the unpaid filed years, none of which were counts of conviction. In a Title 26 case, restitution usually comes through the plea agreement or as a condition of supervised release, and plea agreements in tax cases commonly provide for the full loss, not just the charged years.
The order does not end the collection side. The IRS can assess restitution ordered in a tax case and collect it with its own tools, and a federal appeals court held this year that it is not bound by the payment schedule the sentencing judge set. That is the subject of When Restitution Isn't the End of It.
Triage: file late, or decide on disclosure first
Most people who are behind on filing have a civil problem. The fix is to file accurate returns, address the balance, and ask for penalty relief where it is available. They do not need a criminal tax lawyer, and nothing in the Simes case should frighten them into thinking otherwise.
The decision changes when several of these are true:
- Multiple years unfiled, with substantial income.
- Extensions filed for years that never got a return.
- A professional license, or income the IRS already sees on W-2s and 1099s.
- Any affirmative act: money moved into another name, cash income kept off the books, or a misleading statement to a revenue officer.
- Signs the IRS has already started: a revenue officer asking about unfiled years, a contact from a special agent, or a bank reporting a subpoena.
With that profile, the first question is whether to make a voluntary disclosure through IRS Criminal Investigation before any returns go in. A disclosure is timely only if it comes before the IRS has opened an examination or investigation of the taxpayer, or has received information about him from a third party (IRM 9.5.11.9). Returns filed without making that decision first are signed admissions, and a quiet late filing does not carry the protection a formal disclosure does. The IRS controls when that window closes.
We don't prepare returns. Our role is the legal decision that comes first, and, when returns are needed, bringing in a CPA at counsel's direction so the conversations about what happened, as distinct from the returns themselves, stay within the attorney-client privilege (United States v. Kovel, 296 F.2d 918 (2d Cir. 1961)).
A note for referring counsel
For CPAs and enrolled agents: the client who wants an extension every year and never delivers the documents is the client to talk to now. Each extension filed can become evidence of the client's knowledge, and Circular 230 Section 10.21 already requires a practitioner who knows a client has not filed to advise the client of the noncompliance and its consequences. When the gap reaches multiple years with real income, bring in criminal tax counsel before the returns are prepared, while a voluntary disclosure is still an option. I am glad to consult with counsel on where a client sits.
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