Criminal Defense Lawyers

Obstruction Enhancement Risks

When Your Past Actions Add Years to Your Federal Sentence

You just recieved your Pre-Sentence Report and saw the words “obstruction of justice enhancement” in black and white. Your attorney said its “only” 2 levels, but you’re hands are shaking because you know what that means: years added to you’re sentence. That deleted Signal conversation from eight months ago? The text messages you wiped before anyone even contacted you? The phone call with your co-defendant where you discussed the case? Any one of these could trigger a federal sentencing enhancement that doubles you’re prison time.

Look, here’s the thing—the federal sentencing guidelines don’t just punish you for the crime you committed. They also punish you for anything the goverment thinks you did to interfere with there investigation or prosecution. And the bar for “obstruction” is alot lower then you think.

This article explains exactly what triggers obstruction enhancements, the hidden penalties prosecutors don’t mention, the critical 14-day deadline to fight it, and your four tactical options based on 2024-2025 case law that your public defender might not even know exists yet.

What the Obstruction Enhancement Actually Means (And Why It’s Worse Than They’re Telling You)

The obstruction of justice enhancement is found in USSG §3C1.1 of the Federal Sentencing Guidelines. When applied, it adds two levels to you’re base offense level.

Sounds simple, right?

Two levels equals maybe six months, maybe a year depending on where you fall in the sentencing table.

Wrong.

Here’s what they’re not telling you: if the obstruction enhancement is applied, you also lose your acceptance of responsibility reduction under USSG §3E1.1. That reduction is worth 2-3 levels if you plead guilty and accept responsibility for you’re conduct. So your not just fighting a 2-level increase—your fighting a 4-5 level effective increase when you lose both the enhancement and the reduction.

Let me break down what that actually means in time. For someone at Criminal History Category I (no prior record) with a base offense level of 20:

Base level 20 with acceptance reduction (level 17) = 24-30 months. Base level 20 with obstruction enhancement and NO acceptance (level 22) = 41-51 months.

That’s the diffrence between two years and four years. Based off the same underlying crime.

The enhancement applies if you’re “obstructive conduct” occured with respect to the investigation, prosecution, or sentencing of you’re offense. Note that last part—sentencing. Most people think if they made it through trial or plead guilty, there safe from obstruction allegations. Wrong. If you submit false letters of support to the sentencing court, if you lie in your sentencing memorandum, if you influence witnesses during the pre-sentence investigation, the enhancement can still apply.

And here’s the really critical part: the goverment only needs to prove obstruction by a preponderance of the evidence—meaning 51% likelihood, not “beyond a reasonable doubt.” At sentencing, the rules change. The burden of proof drops from 99% certainty to basically “more likely than not.” Federal judges can find you obstructed justice based on evidence that wouldn’t have been enough to convict you at trial.

You also need to understand the timeline your working with. Under Federal Rule of Criminal Procedure 32, the probation office must disclose your Pre-Sentence Report (PSR) at least 35 days before sentencing. You then have exactly 14 days to file objections to anything in that report—including any recommendation for obstruction enhancement. Miss that deadline, and you’ve waived you’re right to challenge it. Not just at sentencing, but on appeal to. Procedural default means your stuck with whatever the PSR says.

I mean, think about it: 14 days to research case law, gather evidence, draft legal objections, and file them with the court. While your also preparing for the biggest court date of you’re life. The system is designed to overwhelm you.

What Conduct Actually Triggers the Enhancement (The Lines Are Blurrier Than You Think)

So what exactly constitutes “obstruction”? The guidelines list specific examples, but there the ones that seem obvious:

• Threatening, intimidating, or otherwise unlawfully influencing a witness
• Committing perjury or suborning perjury
• Producing or attempting to produce a false, altered, or counterfeit document or record
• Destroying or concealing evidence
• Making false statements to law enforcement or investigators
• Providing materially false information to a probation officer

But here’s where it gets tricky. Each of those categories is broader then you think, and federal prosecutors have gotten very creative about what counts as “obstruction.”

Deleted Messages and the “Pre-Investigation” Problem

Lets say you deleted text messages or emails six months before anyone from the FBI contacted you. You had no idea there was going to be an investigation. Maybe you just routinely clear old messages, or you was worried about privacy for legitimate reasons.

Does that count as obstruction?

The answer is: it depends on which federal circuit your in.

In U.S. v. Martinez (SDNY, September 2024), the court held that the obstruction enhancement does not apply if you deleted evidence before you knew—or should of known—that an investigation was pending or imminent. The court said the goverment has to prove you knew or reasonably anticipated an investigation when you destroyed the evidence.

But in the Fifth Circuit, the standard is different. In U.S. v. Lopez (March 2024), the court applied the enhancement even though the defendant deleted evidence before receiving any subpoena or contact from investigators. The court said the defendant “should have known” an investigation was likely based off the nature of his conduct.

So if your in the Southern District of New York, you might have a viable defense. If your in Texas or Louisiana, your probly facing an uphill battle.

Here’s the thing—and this is crucial for anyone reading this in 2025—the Department of Justice has launched what they call a Cyber Obstruction Initiative. There specifically targeting defendants who use encrypted messaging apps like Signal, Telegram, or WhatsApp, especially those with disappearing message features. Prosecutors are arguing that the mere use of encrypted apps shows “consciousness of guilt” and intent to obstruct.

The data backs this up: in 2023, obstruction enhancements was applied in 28% of cybercrimes and cryptocurrency cases. In 2024, that number jumped to 41%. If you’re case involves any digital evidence and you used encrypted communications, the prosecution is gonna argue you was trying to hide evidence.

Real talk: even if you was using Signal for completely legitimate privacy reasons—because your a journalist, because you work in a sensitive industry, because you value privacy—prosecutors will twist it into evidence of criminal intent. I’ve seen it happen.

Talking to Witnesses: The Hair Trigger Problem

You might think you can talk to a co-defendant or potential witness about the case, as long as your not asking them to lie.

Wrong.

In U.S. v. Williams (11th Circuit, October 2024), the court applied the obstruction enhancement where the defendant simply “reminded” a co-defendant of certain exculpatory facts—facts that was actually true. The defendant didn’t ask anyone to lie. He just discussed there shared recollection of events. The court said any communication about testimony is inherently suspect and can support an obstruction finding.

Compare that to the Ninth Circuit, which requires the goverment to prove you actually intended to corrupt or influence testimony, not just that you talked about the case. Same conduct, different result depending on were your charged.

Bottom line: if your facing federal charges and you talk to anyone who might be a witness—coworkers, friends, family members who was present for relevant events—the prosecution can characterize it as witness tampering irregardless of you’re intent.

Trial Testimony as “Perjury”

If you go to trial and testify in you’re own defense, be aware: if the jury convicts you, the prosecution will argue that you’re testimony was false and constitutes perjury for purposes of the obstruction enhancement. Even if they never charged you with perjury. Even if you’re testimony was just you’re version of disputed events.

This is part of what defense attorneys call the “trial tax.” Defendants who go to trial face the obstruction enhancement in 43% of cases. Defendants who plead guilty face it in only 19% of cases. The system punishes you for exercising you’re constitutional right to a trial.

The Pre-Sentence Report Timeline Trap (14 Days to Save Years)

Let me walk you through how this actually plays out, because the timeline is everything and most people don’t realize there in a race against the clock untill its to late.

After you’re convicted (whether by plea or trial), the court orders a Pre-Sentence Investigation. A probation officer interviews you, reviews the evidence, talks to the prosecution, and drafts the Pre-Sentence Report (PSR). This document recommends you’re sentencing range based on the guidelines.

If the probation officer believes you obstructed justice—or if the prosecution pushes for it—the PSR will include a recommendation to apply the §3C1.1 enhancement. That’s often the first time you’ll see it in writing.

Under Fed. R. Crim. P. 32, the probation office must give you the PSR at least 35 days before sentencing. You then have exactly 14 days to file written objections. Not 14 business days—14 calender days.

If you don’t object within that window, you’ve waived you’re right to challenge the enhancement. At sentencing, the judge will likely adopt the PSR’s recommendation without much discussion. And on appeal? Appellate courts will review for “plain error” only—a nearly impossible standard to meet. You’ve basically lost before you started.

Here’s what makes this even more of a trap: the probation officer who writes you’re PSR isn’t bound by the same evidentiary rules as a trial. They can include hearsay, speculation, and assumptions. And courts give there recommendations alot of weight.

But—and this is were recent case law helps you—there not supposed to just guess.

In U.S. v. Thompson (Third Circuit, December 2024), the court reversed an obstruction enhancement that was based solely on the probation officer’s speculation. The PSR said the defendant “must have” deleted text messages because there was no messages from a certain time period in the evidence. No proof of deletion. No forensic analysis. Just absence of evidence treated as evidence of obstruction.

The Third Circuit said that’s not good enough. The goverment needs actual evidence of obstructive conduct, not just suspicion based off what’s missing. This is huge, because probation officers do this all the time—they see gaps in the evidence and assume the defendant destroyed something.

If you’re PSR includes obstruction enhancement language and it’s based on the probation officer’s assumptions rather then hard evidence, Thompson gives you ammunition to fight it. But you have to object within that 14-day window.

So here’s what you need to do the moment you recieve you’re PSR:

Read it immediately. Don’t wait. Look for any mention of obstruction, §3C1.1, or conduct that could be characterized as obstructive. Note the factual basis: is it actual evidence or speculation? Calender the objection deadline (14 days from disclosure). Contact an attorney who knows the 2024-2025 case law, not just the guidelines.

The prosecution is counting on you not knowing this. There counting on you missing the deadline or not understanding that you can challenge the factual basis of the probation officer’s recommendations.

The Hidden Penalties and Double-Counting Traps

Let’s talk about what this actually costs you, because the “2-level enhancement” language makes it sound almost bureaucratic. Clean. Technical.

But were talking about years of you’re life.

I already explained the acceptance of responsibility problem: lose that reduction and the enhancement isn’t 2 levels, its 4-5 levels effective increase. But there’s more traps most people don’t see coming.

The Sentencing Table Math

Your sentence is determined by where you fall on the sentencing table—a grid based on you’re offense level (vertical axis) and criminal history category (horizontal axis). Each level increase moves you up the table, and the higher you go, the bigger the jumps.

At lower offense levels, a 2-level increase might only add 4-6 months. But at higher offense levels—common in fraud, drug trafficking, and conspiracy cases—a 2-level increase can add 12-18 months. And remember, your not just adding 2 levels. Your adding 2 for obstruction and losing 2-3 for acceptance. That 4-5 level swing can mean:

Offense level 25 (no enhancement, with acceptance at 22): 41-51 months. Offense level 25 (with enhancement, no acceptance at 27): 70-87 months.

That’s the diffrence between 3.5 years and 7 years. For the same underlying crime. The obstruction enhancement don’t just add time—it fundamentally changes you’re life trajectory.

And it gets worse. If you was already facing a mandatory minimum sentence, the enhancement can push you above the guidelines range, giving the judge less discretion to sentence below the mandatory minimum.

The Trial Tax in Numbers

Here’s something prosecutors won’t say out loud but defense attorneys know: if you excercise you’re constitutional right to a trial, your far more likely to face the obstruction enhancement.

According to U.S. Sentencing Commission data from 2024, defendants who went to trial faced obstruction enhancements in 43% of eligible cases. Defendants who plead guilty faced it in 19% of cases. That’s a 24-point gap.

Why? Because if you testify at trial and the jury convicts you, prosecutors argue you’re testimony was perjury. If you put on a defense, they argue you was obstructing by contesting there case. If you file pretrial motions challenging the evidence, they say you was trying to suppress there investigation.

The system punishes you for fighting. And that punishment ain’t just the risk of losing at trial—its the near-certainty of an obstruction enhancement on top of whatever sentence you’d of gotten if you’d plead guilty.

I mean, think about it. You was told you have the right to a trial. The Constitution guarantees it. But excercise that right and the goverment will argue you obstructed justice by making them prove there case.

Its fundamentally broken.

The Sophisticated Means Double-Count Trap

If your facing white-collar charges—fraud, money laundering, tax evasion—there’s another trap you need to know about. USSG §2B1.1(b)(10)(C) adds 2 levels if you’re offense involved “sophisticated means.” This usually applies when you used complex financial structures, encrypted communications, offshore accounts, or other methods to conceal the crime.

Now here’s the problem: if you encrypted or destroyed documents as part of that sophisticated scheme, prosecutors will argue you should get both the sophisticated means enhancement and the obstruction enhancement. Same conduct, two enhancements, 4 additional levels.

Whether courts allow this double-counting depends on which circuit your in. The Second and Fourth Circuits have allowed it, reasoning that sophisticated means relates to the crime itself while obstruction relates to the investigation. The Ninth Circuit has prohibited it, saying you can’t punish the same conduct twice under different guidelines provisions.

If your facing both enhancements, this is a 4-level fight—potentially years of difference—and it depends entirely on were you’re charged and whether you’re attorney knows to raise the double-counting objection.

But There’s Hope: Judicial Discretion Post-Booker

Here’s the thing that keeps me going in these cases: the guidelines are advisory, not mandatory. After United States v. Booker, federal judges have discretion to depart downward from the guidelines even when an enhancement technically applies.

And some judges use that discretion. According to sentencing data from 2020-2024, federal judges depart downward from obstruction enhancement recommendations in about 23% of cases. That’s nearly one in four.

Which judges? It varies. Some judges think obstruction enhancements are over-applied and are skeptical of prosecutorial recommendations. Others apply them mechanically. If you’re case has been assigned to a judge, you’re attorney should research that judge’s sentencing patterns—how often they apply enhancements, how often they depart, what arguments they respond to.

This is were local knowledge matters. A federal defense attorney who regularly practices in you’re district will know which judges are enhancement-skeptical and which arguments resonate with them. A lawyer from out of state or someone who doesn’t specialize in federal sentencing won’t have that intelligence.

Recent Case Law Giving You a Fighting Chance (2024-2025 Developments)

If your facing an obstruction enhancement, you need to know about four cases from the last 18 months that have tightened the standards and created openings for defense challenges. You’re lawyer should be citing these in you’re PSR objections and at sentencing.

1. U.S. v. Martinez (SDNY, September 2024): The Pre-Investigation Deletion Defense

Martinez deleted WhatsApp messages eight months before the FBI contacted him. The goverment argued he “should of known” an investigation was coming based on the nature of his buisness activities. The court disagreed.

The court held that for the obstruction enhancement to apply, the defendant must have had actual or constructive knowledge that an investigation was pending or imminent when they destroyed evidence. Routine deletion of old messages—even if it turns out that evidence was relevant—doesn’t meet that standard if it occured before the investigation began.

This case is critical if you deleted emails, texts, or documents before receiving a subpoena, target letter, or any investigative contact. The goverment has to prove you knew the investigation was coming, not just that you should of been suspicious.

2. U.S. v. Thompson (Third Circuit, December 2024): Speculation Isn’t Evidence

Thompson’s PSR recommended obstruction enhancement because “the defendant must have deleted text messages” given that certain time periods had no messages in the evidence. No forensic analysis. No proof of deletion. Just absence.

The Third Circuit reversed, holding that the probation officer’s speculation isn’t sufficient. The goverment needs actual evidence of obstructive conduct—forensic proof of deletion, witness testimony, admissions, something concrete. You can’t just assume someone obstructed because evidence is missing.

If you’re PSR bases the enhancement on assumptions or gaps in the evidence, Thompson is you’re blueprint for challenging it. Demand actual proof.

3. U.S. v. Chen (Ninth Circuit, August 2024): Sentencing Phase Obstruction Applies

This one cuts the other way, but you need to know about it. Chen submitted fabricated letters of support to the sentencing court—letters purportedly from community members who didn’t actually write them or didn’t say what the letters claimed.

The Ninth Circuit upheld the obstruction enhancement, emphasizing that USSG §3C1.1 applies to obstruction during the investigation, prosecution, or sentencing phase. Lying to the probation officer, submitting false documents in support of a lower sentence, or providing materially false information during the PSR interview all qualify.

The takeaway: you’re not safe from obstruction allegations just because you’ve plead guilty or been convicted. The sentencing process itself is covered, and prosecutors are looking for any misstatements or false information you provide during that phase.

4. U.S. v. Williams (Eleventh Circuit, October 2024): Witness Contact Is a Minefield

Williams called a co-defendant and reminded him of there shared recollection of certain events. He didn’t ask the co-defendant to lie. He didn’t threaten him. He just discussed what they both remembered.

The Eleventh Circuit applied the obstruction enhancement anyway, reasoning that any contact with potential witnesses about there testimony is suspect and can constitute obstruction. The court said it doesn’t matter if you didn’t explicitly ask them to lie—the fact that you discussed testimony shows intent to influence.

This case is a warning: if your facing charges with co-defendants or if there’s potential witnesses who are friends, family, or colleagues, do not contact them about the case. Any conversation can be twisted into witness tampering.

These four cases from 2024 show the landscape is shifting. Courts are demanding more proof from prosecutors in some circuits (Martinez, Thompson) while expanding the definition of obstruction in others (Chen, Williams). You’re defense depends on knowing which arguments work in you’re jurisdiction and which recent cases support you’re position.

Your Four Options Right Now (What to Do in the Next 48 Hours)

If your reading this because you’ve received a PSR with obstruction enhancement language, or because you’re attorney warned you its coming, or because your worried about past conduct that might be characterized as obstruction, here’s what you need to do immediately:

Option 1: File a PSR Objection (If Your Still Within the 14-Day Window)

If you recieved you’re PSR within the last 14 days, you’re first priority is filing a written objection. This needs to be done by someone who knows federal sentencing law and the recent case law.

You’re objection should:

• Challenge the factual basis (cite Thompson if its based on speculation)
• Argue lack of knowledge (cite Martinez if conduct was pre-investigation)
• Distinguish you’re conduct from the examples in the guidelines
• Request an evidentiary hearing if there’s disputed facts
• Cite circuit-specific precedent on burden of proof and standards

Missing this deadline means you’ve waived the objection. Don’t let that happen.

Option 2: Negotiate With the Prosecution (If Your Pre-Sentencing)

If your still in plea negotiations or if sentencing hasn’t occured yet, there may be room to negotiate the enhancement away. Prosecutors sometimes agree to withdraw obstruction allegations in exchange for other concessions—cooperation, restitution, agreement not to appeal.

This requires leverage, which usually means you have a viable defense to the enhancement or you have something the goverment wants (information, cooperation, fast resolution). A skilled federal defense attorney can assess whether negotiation is viable in you’re case.

Option 3: Prepare for Sentencing Advocacy (If Objections Have Been Filed)

Even if the court overrules you’re objections and finds the enhancement applies, you’re attorney can still argue for a downward departure at sentencing. Remember: 23% of federal judges depart downward even when enhancements technically apply.

Effective sentencing advocacy involves showing the enhancement overstates the seriousness of the obstruction, distinguishing you’re case from typical obstruction cases, arguing the guidelines are advisory and a lower sentence is sufficient.

Option 4: Preserve the Issue for Appeal (If All Else Fails)

If the district court applies the enhancement over you’re objections, you need to preserve the issue for appeal. Only 12% of obstruction enhancements are reversed on appeal, but that’s not zero. Recent cases like Thompson show appellate courts will reverse when the enhancement is based on insufficient evidence.

To preserve the issue, you’re attorney must object at every stage, create a clear record, cite controlling circuit precedent, and file a timely notice of appeal (14 days after sentencing).

The key is acting fast. The clock is running from the moment you recieved you’re PSR. Every day you wait is a day you can’t get back.

The 14-Day Deadline Doesn’t Care About Your Fear

Right now, the prosecution is drafting there response to you’re PSR. Right now, the probation officer is finalizing recommendations. Right now, the clock is ticking toward you’re sentencing date.

The only variable is whether you fight this with someone who knows the 2024 case law or whether you walk into that courtroom with hope instead of strategy.

The obstruction enhancement isn’t just a technical guideline adjustment. Its the goverments way of punishing you twice—once for the crime, once for protecting yourself.

But you don’t have to accept it without a fight.

Recent case law from 2024 and 2025 has created openings that didn’t exist two years ago. Courts are demanding actual evidence, not speculation. There recognizing that pre-investigation conduct may not qualify irregardless of what the probation officer thinks. Judges are exercising discretion to depart downward when the enhancement overstates culpability.

But none of that matters if you miss the 14-day objection deadline. None of it matters if you’re attorney doesn’t know these cases exist. And none of it matters if you wait untill its to late to act.

You’re sentencing date is fixed. You’re objection deadline is fixed. The only thing you can control is what you do right now, today, in the next 48 hours.

The question is whether you’ll fight this with every tool available or whether you’ll let the system steamroll you because you didn’t know you had options.

Your facing years of you’re life.

That’s worth making a phone call.