United States v. Karagianis: The Seventh Circuit Clarifies that Omission of a § 3582(c)(2) Appeal-Waiver During a Rule 11 Colloquy Is Not Plain Error Absent a Showing of Prejudice

1. Introduction

United States v. Nicholas Karagianis, No. 23-2820 (7th Cir. July 11 2025), presented the Court of Appeals with intertwined questions of plea-agreement enforcement, Rule 11 compliance, and sentencing procedure. Nicholas Karagianis pled guilty to federal drug-distribution and felon-in-possession charges pursuant to a non-binding plea agreement that (1) stipulated a total Guidelines offence level of 31 and (2) contained an unusually detailed waiver structure, including a waiver of any appeal from an adverse ruling on a future motion for sentence reduction under 18 U.S.C. § 3582(c)(2). At sentencing, the district court adopted the Presentence Report’s higher offence level of 33, imposed a below-Guidelines sentence, and—during the plea colloquy—failed expressly to mention the waiver of a § 3582(c)(2) appeal.

On appeal, Karagianis argued:

Rule 11 error: the court omitted the specific § 3582(c)(2) appeal-waiver and inadequately explained the role of the PSR.
Government breach: the prosecution failed to object when the PSR recommended a higher offence level than the parties had stipulated.

The Seventh Circuit (Judges Hamilton, Lee, and Maldonado; opinion by Judge Lee) affirmed, creating an important clarification on what constitutes “plain error” where a court neglects to verbalise a limited appellate waiver during a Rule 11 colloquy.

2. Summary of the Judgment

The court recognised that the district judge did err by not specifically advising Karagianis that he was waiving any appeal from a future adverse § 3582(c)(2) ruling. Nevertheless, applying plain-error review, it held:

The error was not “plainly” prejudicial: Karagianis failed to show a reasonable probability that, but for the omission, he would have refused the plea.
The omission did not seriously affect the fairness, integrity, or public reputation of judicial proceedings.
The district court’s explanation of the Guidelines and PSR satisfied Rule 11(b)(1)(M); no explicit PSR tutorial is required.
The government did not clearly breach the plea agreement by remaining silent on the PSR’s higher offence level; even if it did, no substantial-rights prejudice occurred because the imposed sentence fell at the bottom of the range the parties had stipulated.

3. Detailed Analysis

3.1 Precedents Cited and Their Influence

United States v. Dominguez Benitez, 542 U.S. 74 (2004) – Core precedent on Rule 11 plain-error review; requires defendant to show a reasonable probability he would have refused the plea but for the error. The Seventh Circuit applied this framework to the omitted § 3582 waiver.
United States v. Sura, 511 F.3d 654 (7th Cir. 2007) – The Court distinguished Sura (total absence of waiver discussion, vulnerable defendant) emphasizing that Karagianis was educated, coherent, and had acknowledged reading the agreement.
United States v. Navarro, 817 F.3d 494 (7th Cir. 2015) – Source of the four-prong plain-error test reiterated in this case.
United States v. Wyatt, 982 F.3d 1028 (7th Cir. 2020) and United States v. Collins, 986 F.3d 1029 (7th Cir. 2021) – Govern scope and remedy for alleged plea-agreement breaches; relied on to determine no substantial-rights prejudice.
United States v. Woods, 581 F.3d 531 (7th Cir. 2009) – Cited regarding ambiguity about whether similar waiver language bars § 3582 appeals; the Court used it to highlight how unusual and non-obvious the Karagianis waiver was.
Inter-circuit cases (Gall, Ellis, Lovelace) – Surveyed to show doctrinal division over whether silence amounts to a breach, reinforcing that any breach here was not “plain.”

3.2 Legal Reasoning

Plain-Error Framework. The court meticulously applied the four prongs: error, clarity, prejudice, and reputational impact. Only the first prong (existence of error) was satisfied.
Totality-of-the-Circumstances Assessment. To gauge prejudice, the panel looked at contemporaneous evidence: defendant’s age, education, sworn statements, written acknowledgment, and the speculative nature of a future § 3582 amendment.
Narrow Construction of Contractual Duties. Concerning breach, the court parsed the agreement’s text and noted the government never promised to oppose PSR enhancements, illustrating a restrained, textualist approach.
Sentencing Range Comparison. Even if the plea had been honoured verbatim (offence level 31), the low end of the Guidelines (168 months) equaled the sentence actually imposed; hence, no prejudice.

3.3 Impact of the Decision

By anchoring its holding in the “reasonable probability” standard, the Seventh Circuit sets a functional precedent:

Courts in the circuit need not vacate pleas for every technical mis-step in revealing limited appeal waivers; defendants must link the omission to a plausible decision-making change.
Practitioners drafting plea agreements with nested waivers must advise clients thoroughly; failure to object contemporaneously risks plain-error forfeiture.
Prosecutors face minimal risk of breach findings merely for acquiescing in a PSR that diverges upward, absent an express promise to object.
Future litigation over § 3582 appeal waivers will focus on enforceability and voluntariness; this case foreshadows that such waivers can survive silent colloquy omissions.

4. Complex Concepts Simplified

Rule 11 Colloquy: A required in-court dialogue ensuring the defendant’s plea is voluntary and informed. It serves as a safeguard against later claims of misunderstanding.
Plain-Error Review: When a party fails to object below, the appellate court corrects only errors that are obvious, prejudicial, and harmful to the judiciary’s reputation.
§ 3582(c)(2) Motion: A post-sentencing request for sentence reduction when the Sentencing Commission retroactively lowers a Guidelines range.
Presentence Report (PSR): A document prepared by probation officers detailing offence conduct, criminal history, and recommended Guideline calculations; courts often give it great weight.
Plea-Agreement Breach Doctrine: A contract-law analogue under which courts enforce promises made by both sides; prejudice is required for relief under plain-error review.

5. Conclusion

United States v. Karagianis refines the intersection of appellate waivers, Rule 11 duties, and plain-error doctrine. The Seventh Circuit confirms that:

A court’s failure to articulate a nuanced, limited appeal waiver is an error, yet not “plainly” reversible without a concrete demonstration that the defendant would have rejected the plea.
Rule 11 does not obligate judges to outline the PSR’s procedural mechanics so long as defendants are told that Guidelines will be calculated and considered.
Plea-agreement stipulations bind the parties, not the court; government silence in the face of a higher PSR recommendation is not necessarily a breach.

Practically, the decision urges defense counsel to raise objections contemporaneously and to document any misconceptions that might influence a client’s plea. Strategically, prosecutors drafting complex waiver packages would be wise to ensure that judges explicitly canvass each waiver on the record. Above all, the ruling underscores the judiciary’s commitment to balancing procedural exactitude with pragmatic fairness—a balance that preserves the integrity of plea bargaining without elevating technical missteps into automatic reversals.