Forfeiture of Unraised Rule 11 Challenges and Harmless-Error Review for Plea Colloquy Omissions: United States v. Robert Smith, Jr. (4th Cir. 2025)

Introduction

In United States v. Robert Smith, Jr., the Fourth Circuit affirmed a conviction that followed a guilty plea despite notable omissions in the Rule 11 plea colloquy. The court issued a dual message: district courts must meticulously follow Rule 11, yet the finality of guilty pleas cannot be undone absent a concrete showing of prejudice. The panel (Judge Wilkinson writing, joined by Judges Thacker and Heytens) clarified preservation rules for Rule 11 challenges, applied plain-error and harmless-error frameworks rigorously, reiterated that defects in an appeal waiver do not topple an otherwise valid plea, and applied the six-factor test from United States v. Moore to reject a post-plea withdrawal.

The case arose from an investigation showing that Smith bought fifty-nine firearms over sixteen months while repeatedly listing false Virginia addresses—one of which did not exist—on ATF Form 4473. After a 24-count indictment for making false statements to a federal firearms licensee (18 U.S.C. § 924(a)(1)(A)), Smith pleaded guilty to one count the day before trial in exchange for dismissal of the remaining counts and a three-level acceptance-of-responsibility reduction under U.S.S.G. § 3E1.1. Months later—after his original counsel was recommended for disbarment and ultimately disbarred—Smith moved to withdraw his plea based on ineffective assistance and the incomplete Rule 11 colloquy. The district court denied the motion and imposed a fourteen-month sentence with supervised release. On appeal, Smith challenged the validity of his plea and the denial of his withdrawal motion.

Summary of the Opinion

The Fourth Circuit acknowledged several shortcomings in the plea hearing: the district court failed to explain that the Sentencing Guidelines are advisory and failed to discuss the appeal waiver as required by Rule 11(b)(1)(M) and (N); the court also omitted several best-practice questions from the Federal Judicial Center’s Benchbook (such as inquiries about intoxication, mental health treatment, and whether all plea offers were conveyed). Nonetheless, the court affirmed because:

Preservation: Smith did not challenge the Rule 11 colloquy in the district court; he attacked only counsel’s performance. Therefore, the Rule 11 claim was forfeited and reviewed for plain error, with the burden on Smith.
Prejudice: Smith failed to show a reasonable probability that he would not have pleaded guilty absent the Rule 11 errors. His written plea agreement thoroughly explained the Guidelines and appeal waiver; he confirmed he reviewed it; and the government’s evidence was overwhelming. The court emphasized the finality of guilty pleas.
Appeal waiver: Even if the waiver were deficient, the proper remedy is to sever the waiver rather than to unravel the entire plea agreement.
Plea withdrawal: Applying the Moore factors, the court held that Smith did not present a “fair and just reason” to withdraw. He offered no credible claim of innocence, waited too long to move (approximately 199 days), failed to show but-for prejudice from counsel’s performance, and withdrawal would prejudice the government and waste judicial resources.

Result: Conviction affirmed; denial of plea withdrawal affirmed.

Analysis

Precedents Cited and How They Shaped the Decision

Boykin v. Alabama and Brady v. United States: The court invoked Boykin (requiring that pleas be knowing and voluntary) and Brady (pleas are a grave and solemn act) to underscore the importance of Rule 11 compliance. These cases ground the constitutional solicitousness toward plea canvassing.
McCarthy v. United States: Cited for the proposition that Rule 11 is designed to help district judges make the constitutionally required determination of voluntariness and understanding.
United States v. Lockhart (4th Cir. en banc) and United States v. Sanya (4th Cir.): Examples where the Fourth Circuit has previously admonished district courts to track Rule 11 carefully. They frame the court’s expressed concern about omissions here.
United States v. Wilson (4th Cir.): The court will not “script” Rule 11; not every departure is fatal. This supports a flexible, context-sensitive approach.
United States v. Dominguez Benitez (U.S. Supreme Court): Establishes the standard that a defendant seeking relief for unpreserved Rule 11 error must show a reasonable probability that he would not have pleaded guilty but for the error. Dominguez Benitez also emphasizes the special importance of the finality of guilty pleas.
United States v. Hairston and United States v. Thorne (4th Cir.): Apply the “reasonable probability” prejudice standard in the Rule 11 context.
United States v. Olano (U.S. Supreme Court): Plain-error framework and burden-shifting when error is forfeited, not preserved. The court used Olano to explain why Smith carried the burden on appeal.
United States v. General (4th Cir.): Upholds an appeal waiver where the defendant was represented and had reviewed the written agreement, even when the district court did not expressly question him about it—closely analogous to Smith’s situation.
United States v. Smith, 134 F.4th 248 (4th Cir. 2025): Clarifies that the remedy for an invalid appeal waiver is severance of the waiver clause, not vacatur of the entire plea. The court relied on this principle to show that even a waiver defect would not unravel Smith’s conviction.
United States v. Moore (4th Cir. 1991) and progeny including United States v. Mayberry (4th Cir. 2025) and United States v. Nicholson (4th Cir. 2012): The six-factor framework governing whether a defendant has shown a “fair and just reason” to withdraw a guilty plea, and authority deeming delays of weeks or a few months too long.
United States v. DeFreitas (4th Cir.) and Hill v. Lockhart (U.S. Supreme Court): Ineffective assistance in the plea context requires both deficient performance and a reasonable probability that, but for counsel’s errors, the defendant would have gone to trial.
United States v. Reckmeyer (4th Cir.) and United States v. Dayton (5th Cir. en banc): Acknowledgment that trial judges are human and occasional colloquy deviations happen—context for applying harmless/plain error rather than mandating perfection.
Federal Judicial Center Benchbook: Not binding, but strongly recommended best practices. The court referenced it to note what the district court could have done better.

Legal Reasoning

1) Identified Rule 11 deficiencies. The district court did not explain:

That the Guidelines are advisory and the judge can depart from them (Rule 11(b)(1)(M)).
The appeal waiver (Rule 11(b)(1)(N)).

The court also omitted Benchbook-recommended questions about current intoxication, mental health treatment, and whether all plea offers had been conveyed, and it did not read plea terms verbatim at the hearing. While not Rule 11 violations per se, these omissions weakened the colloquy’s thoroughness.

2) Preservation and standard of review. Crucially, Smith did not challenge the adequacy of the colloquy when he moved to withdraw his plea; he challenged only counsel’s performance. The court held that issues about counsel’s effectiveness and issues about the colloquy are distinct; raising one does not preserve the other. Therefore, the Rule 11 claim was forfeited and reviewed solely for plain error, shifting the burden to Smith to show prejudice under Olano and Dominguez Benitez.

3) No reasonable probability of a different plea decision. The court found that, even with the omissions, the record showed Smith understood the key consequences of pleading guilty:

The written plea agreement, which Smith acknowledged he read and understood, comprehensively explained the sentencing process, the Guidelines’ role, and the appeal waiver.
Smith was represented by counsel and had some college education.
He did not claim impairment or incompetence at the hearing, and nothing in the record suggested he was impaired or unaware.
There was no suggestion of undisclosed plea offers.

Moreover, the counterfactual is telling: had Smith gone to trial, he likely would have lost the acceptance-of-responsibility reduction, faced 23 additional counts, and confronted exceptionally strong government evidence: a non-existent address, residents prepared to testify that he never lived at the other address, and cell-site evidence placing his phone in Maryland at relevant times. On this record, a rational defendant would have maintained the plea agreement.

4) Appeal waiver severability. The panel emphasized that even if the appeal waiver were infirm due to the colloquy omission, the remedy is to sever the waiver—not to vacate the plea. This principle insulates the conviction from the knock-on effects of a waiver error and underscores that plea agreements are not all-or-nothing.

5) Plea withdrawal under Moore. The court rejected the “fair and just reason” claim based on six non-exhaustive factors:

Knowledge and voluntariness: The omissions did not render the plea unknowing or involuntary given the written agreement and the record as a whole.
Assertion of innocence: Smith never asserted legal innocence, and the government’s case was strong. This is often the most weighty factor.
Delay: Approximately 199 days elapsed—far longer than periods previously deemed too long, even when counting from later alternative dates proposed by Smith (e.g., fifty-two days).
Close assistance of competent counsel: Even assuming deficiency, Smith did not show prejudice under Hill v. Lockhart—he never argued that he would have gone to trial but for counsel’s errors. Given the evidence and benefit of the plea, that showing would be particularly difficult.
Government prejudice: With trial preparation already completed and then foregone due to the last-minute plea, requiring the government to reconstruct its case months later would cause prejudice.
Inconvenience/waste: Reopening the case would have required the court to refamiliarize itself and reschedule trial; by the time of appeal, Smith had been released, making further proceedings largely pointless and potentially unjust.

6) Balanced admonition. While affirming, the court repeated its longstanding directive: district courts should hew closely to Rule 11’s text. What may seem redundant to an experienced judge can be a vital protection for a defendant. But departures that cause no prejudice will not undo a plea.

Impact

Preservation clarified: Raising ineffective assistance in a withdrawal motion does not preserve a separate challenge to the Rule 11 colloquy. Defendants must distinctly raise Rule 11 errors below or face plain-error review on appeal. This is a significant procedural clarification for appellate practice in the Fourth Circuit.
Written plea agreements matter: Detailed, signed plea agreements can cure or blunt colloquy omissions, especially for represented defendants, by evidencing understanding of guidelines and waivers.
Appeal waiver severability fortified: The court reaffirmed that even if a waiver is invalidly secured, the remedy is severance—not vacatur of the entire plea—preserving the conviction’s finality while eliminating the defective clause. This reinforces the “contract-like” mutuality of plea bargains.
Moore remains a high bar: Without a credible assertion of innocence, prompt motion, and a concrete showing of but-for prejudice from counsel’s performance, withdrawal will be denied. Delays of weeks or months weigh heavily against withdrawal.
Government prejudice is practical: The court accepted a commonsense view of prejudice—foregone trial preparation and the need to reassemble the case can suffice—especially where the plea came on the eve of trial.
Judicial best practices emphasized: The panel’s reminder to follow Rule 11 and the Benchbook will likely spur district courts to reinforce their colloquy checklists, particularly on advisory Guidelines and appeal waivers, while recognizing that minor missteps are not automatic reversals.

Complex Concepts Simplified

Rule 11 plea colloquy: A scripted set of questions and advisements the judge must deliver to ensure the defendant’s plea is knowing, voluntary, and supported by a factual basis. Key items include maximum penalties, trial rights, the advisory nature of the Guidelines (Rule 11(b)(1)(M)), and any appeal waiver (Rule 11(b)(1)(N)).
Harmless error vs. plain error:
- Harmless error (Rule 11(h)): If errors don’t affect substantial rights, the conviction stands. Typically applied when the issue was preserved.
- Plain error (Olano): When an issue was forfeited (not raised below), the defendant must show a clear error affecting substantial rights and that not correcting it would seriously affect the fairness or integrity of proceedings. In the Rule 11 context, this usually means showing a reasonable probability that the defendant would not have pleaded guilty but for the error (Dominguez Benitez).
Appeal waiver severability: If a waiver of the right to appeal is invalidly obtained, courts can sever the waiver and keep the rest of the plea intact, rather than undoing the entire agreement.
Acceptance of responsibility (U.S.S.G. § 3E1.1): A defendant who admits guilt and accepts responsibility typically receives a two- or three-level sentence reduction; going to trial often forfeits this benefit.
The Moore factors for withdrawing a plea:
- Was the plea knowing/voluntary?
- Has the defendant credibly asserted legal innocence?
- How long was the delay before seeking withdrawal?
- Did the defendant receive close assistance of competent counsel, and would he have gone to trial but for counsel’s errors?
- Would withdrawal prejudice the government?
- Would withdrawal inconvenience the court or waste resources?
These factors are non-exhaustive and collectively guide whether there is a “fair and just reason” to allow withdrawal.

Conclusion

United States v. Robert Smith, Jr. is an instructive, published reaffirmation of two core principles: first, guilty pleas will not be undone for imperfect Rule 11 colloquies absent a concrete showing of prejudice; and second, post-plea withdrawal remains an exceptional remedy, governed by a stringent, factor-based inquiry that demands prompt action, credible claims of innocence, and demonstrable but-for prejudice from counsel’s errors. The decision also cements two procedural clarifications of practical importance:

Preservation matters—raising ineffective assistance does not preserve a separate Rule 11 challenge; unpreserved Rule 11 claims face the steep plain-error standard.
Defective appeal waivers are severable; they do not automatically invalidate the entire plea bargain.

The court’s message is balanced: district courts must “dot i’s and cross t’s” in plea colloquies, yet appellate courts must respect the finality of negotiated pleas in the absence of prejudice. For judges, prosecutors, and defense counsel in the Fourth Circuit, Smith confirms both the importance of meticulous Rule 11 practice and the high threshold defendants must meet to unwind a guilty plea.