Date: Mar 3, 2026

Eleventh Circuit Enforces Knowing-and-Voluntary Sentence-Appeal Waivers and Channels Guilty-Plea Ineffectiveness Claims to § 2255 Absent a Developed Record

Introduction

United States v. Beatriz Toledo (11th Cir. Feb. 27, 2026) addresses two recurring post-plea appellate issues: (1) whether a defendant may pursue sentencing challenges despite a plea-agreement appeal waiver, and (2) whether an ineffective-assistance-of-counsel claim tied to the guilty plea can be decided on direct appeal. The defendant, Beatriz Toledo, pleaded guilty in the Southern District of Florida to three counts of aiding and assisting in the preparation of false tax returns under 26 U.S.C. § 7206(2), receiving a 57-month sentence. On appeal, she challenged the procedural and substantive reasonableness of her sentence (including application of a sophisticated-means enhancement) and alleged ineffective assistance of counsel in the district court. The government moved to dismiss the appeal based on the plea agreement’s sentence-appeal waiver.

Summary of the Opinion

The Eleventh Circuit (per curiam) held that Toledo’s sentencing challenges are barred by a knowing and voluntary sentence-appeal waiver that was carefully explained during the Fed. R. Crim. P. 11 plea colloquy. Because none of the waiver’s listed exceptions applied, the court dismissed the sentencing portion of the appeal.

As to ineffective assistance, the court declined to adjudicate the claim on direct appeal because the record was insufficiently developed. The panel therefore affirmed the convictions without prejudice, expressly permitting Toledo to raise the ineffective-assistance claim in a later 28 U.S.C. § 2255 proceeding.

Analysis

Precedents Cited

1) Enforceability and scope of appeal waivers

King v. United States, 41 F.4th 1363 (11th Cir. 2022): The court relied on King for de novo review of waiver validity/scope and for recognized, narrow circumstances where a waiver may not be applied (e.g., jurisdictional defects; constitutionally impermissible factors like race; “extreme circumstances”; or a sentence exceeding the statutory maximum). The opinion invoked King to emphasize that none of those extraordinary circumstances were present.
United States v. Bushert, 997 F.2d 1343 (11th Cir. 1993): Bushert supplied the controlling test for whether a waiver is knowing and voluntary—either the district court specifically questions the defendant about the waiver during the plea colloquy, or the record makes clear the defendant understood its significance. The panel applied Bushert directly, finding the district court “specifically questioned” Toledo and accurately explained the waiver and its exceptions.
United States v. Boyd, 975 F.3d 1185 (11th Cir. 2020): Cited for the “touchstone” formulation—whether it was clearly conveyed that the defendant was giving up the right to appeal “under most circumstances.” The opinion treated the district court’s detailed, exception-by-exception explanation as satisfying Boyd.
United States v. Bascomb, 451 F.3d 1292 (11th Cir. 2006): Used for the proposition that the Eleventh Circuit “consistently enforced” knowing and voluntary waivers “according to their terms.” Once validity was established, Bascomb supported straightforward enforcement of the waiver as written.
United States v. Grinard-Henry, 399 F.3d 1294 (11th Cir. 2005): Reinforced that an appeal waiver bars even “difficult or debatable” issues and “even blatant error.” This citation underscores the court’s unwillingness to engage Toledo’s guideline-enhancement and reasonableness arguments once the waiver was found valid.
United States v. Medlock, 12 F.3d 185 (11th Cir. 1994): Supported the “strong presumption” that the defendant’s sworn colloquy statements are true. The court used Medlock to credit Toledo’s affirmative responses that she understood the waiver and had discussed it with counsel.
United States v. Howle, 166 F.3d 1166 (11th Cir. 1999): Cited (via King) for the “public flogging” example illustrating rare “extreme circumstances” that might justify overlooking an otherwise valid waiver. The opinion used this line to emphasize the narrowness of any equitable escape hatch.
United States v. Hardman, 778 F.3d 896 (11th Cir. 2014): Supplied a contract-interpretation principle: plea agreement language gets its “ordinary and natural meaning.” This supported reading Toledo’s waiver to cover the exact sentencing issues she raised.

2) Ineffective assistance claims on direct appeal vs. collateral review

United States v. Rodriguez, 582 F.2d 1015 (5th Cir. 1978) and United States v. Ungar, 794 F.2d 640 (11th Cir. 1986): These cases supported the disposition “affirmed without prejudice” to raise ineffective assistance in a proper § 2255 proceeding when the record is undeveloped.
Bonner v. City of Prichard, 661 F.2d 1206 (11th Cir. 1981) (en banc): Used to explain why pre-October 1981 Fifth Circuit decisions (like Rodriguez) are binding in the Eleventh Circuit.
United States v. Patterson, 595 F.3d 1324 (11th Cir. 2010) and Massaro v. United States, 538 U.S. 500 (2003): These authorities framed the “preferred means” of resolving ineffective assistance through a § 2255 motion, even if the direct-appeal record hints at attorney deficiencies, because collateral proceedings permit factual development.
United States v. Verbitskaya, 406 F.3d 1324 (11th Cir. 2005), abrogated in part on other grounds by United States v. Durham, 795 F.3d 1329 (11th Cir. 2015) (en banc), and United States v. Merrill, 513 F.3d 1293 (11th Cir. 2008): Cited for the “rare instance” standard—direct review is appropriate only when the record is sufficiently developed. The panel concluded Toledo’s case did not qualify.
Strickland v. Washington, 466 U.S. 668 (1984): Provided the two-part framework (deficient performance and prejudice) that would govern any later § 2255 adjudication, and highlighted why a complete evidentiary record is often essential.

3) Waiverability of ineffective assistance and non-jurisdictional enforcement

In re Sealed Case, 901 F.3d 397 (D.C. Cir. 2018) and Williams v. United States, 396 F.3d 1340 (11th Cir. 2005): The opinion acknowledged a circuit split on whether ineffective-assistance claims can be waived, noting the D.C. Circuit’s approach (collecting cases) and the Eleventh Circuit’s willingness to enforce such waivers in some circumstances. But the court treated the debate as “of no moment” here because the waiver text primarily addressed sentencing appeals and, critically, the government did not seek dismissal of the ineffective-assistance claim based on the waiver.
United States v. Lopez, 562 F.3d 1309 (11th Cir. 2009), United States v. McCarthren, 707 F. App’x 951 (11th Cir. 2017), and United States v. Story, 439 F.3d 226 (5th Cir. 2006): These cases were cited to support the broader point that certain non-jurisdictional limitations (including appeal waivers and claim-processing rules) are generally enforced when invoked, but are not themselves jurisdictional and can be forfeited or waived by the party who would benefit. This helped explain why the court did not reach whether the plea waiver barred ineffective assistance in this posture.

Legal Reasoning

Determining waiver validity (knowing and voluntary): The court focused on the Rule 11 colloquy. The district judge explicitly told Toledo that by pleading guilty she could not appeal her sentence “except for some very, very narrow exceptions,” then enumerated the three exceptions mirrored in the agreement: (i) if the government appeals; (ii) if the sentence exceeds the statutory maximum; or (iii) if the court imposes a sentence above the advisory guideline range. Toledo confirmed she understood and had discussed the waiver with counsel, and both sides agreed the court’s summary was accurate. Under United States v. Bushert and United States v. Boyd, that was enough.
Applying the waiver “according to its terms”: Invoking United States v. Bascomb and United States v. Hardman, the panel treated the waiver as a contract-like provision. Because Toledo’s sentence was within the guideline range, below the statutory maximum, and the government did not appeal, none of the express exceptions applied.
No extra-textual “escape” from the waiver: The opinion emphasized the Eleventh Circuit’s longstanding willingness to enforce waivers even where alleged errors are serious (United States v. Grinard-Henry), while recognizing only narrow exceptions (as summarized in King v. United States)—none of which Toledo established.
Separating sentencing-waiver enforcement from guilt-stage ineffective assistance: The court acknowledged that ineffective assistance claims can relate to the voluntariness of the plea itself and thus are often not foreclosed by a mere sentencing appeal waiver. But it avoided mapping the “contours” of that issue because the government only moved to dismiss the sentencing challenges.
Declining to decide ineffective assistance on direct appeal: Relying on Massaro v. United States, United States v. Patterson, and the “rare instance” line of cases (United States v. Verbitskaya; United States v. Merrill), the panel held the record lacked the necessary factual development—Toledo had not raised ineffectiveness in the district court and the existing record did not obviously demonstrate deficiency or prejudice. The court therefore affirmed the convictions without prejudice to § 2255 litigation, citing United States v. Rodriguez and United States v. Ungar.

Impact

Reinforcement of waiver-centric appellate screening: The decision strengthens the practical reality that, in the Eleventh Circuit, a properly explained appeal waiver will usually end sentencing appeals at the threshold—regardless of whether the defendant frames the sentencing issue as guideline error (e.g., sophisticated means) or reasonableness.
Drafting and colloquy discipline: The outcome illustrates how the government can secure predictable finality through precise waiver language and a meticulous Rule 11 colloquy that enumerates exceptions on the record, invites the defendant’s confirmation, and obtains party assent to the court’s summary.
Channeling ineffective-assistance litigation to § 2255: The opinion reiterates that ineffective-assistance claims will ordinarily be deferred to collateral proceedings where evidence outside the trial/plea record (attorney advice, strategic considerations, communications, and prejudice proof) can be developed.
Strategic lessons for defendants and counsel: Defendants seeking to preserve sentencing review must negotiate narrower waivers or ensure an applicable exception. Those contemplating an ineffective-assistance challenge should recognize that direct appeal is usually an ill-suited vehicle unless the record is already fully developed.
Scope caution regarding “waiver of conviction challenges”: Toledo’s agreement also purported to waive certain conviction-related claims (constitutional and “scope of statute” arguments). While not litigated here, the opinion’s structure signals that courts may parse waiver types (sentencing vs. conviction vs. collateral) rather than treating “waiver” as monolithic.

Complex Concepts Simplified

Sentence-appeal waiver: A provision in a plea agreement where the defendant gives up most rights to appeal the sentence. Courts enforce it if the defendant knowingly and voluntarily agreed—typically proven through the plea colloquy.
Rule 11 plea colloquy: The in-court Q&A required by Fed. R. Crim. P. 11 to ensure a guilty plea is voluntary, informed, and supported by an adequate factual basis. Careful discussion of any appeal waiver is central to later enforcement.
Advisory guideline range: The sentencing range recommended by the U.S. Sentencing Guidelines after calculating offense level and criminal history. “Advisory” means the judge must consider it but is not strictly bound by it.
Upward departure / upward variance: An upward departure is an increase based on guideline-authorized reasons; an upward variance is an increase based on the statutory sentencing factors outside the guideline structure. Toledo’s waiver allowed an appeal if the district court sentenced above the guideline range it established.
Procedural vs. substantive reasonableness: Procedural reasonableness concerns the method (correct guideline calculation, adequate explanation, proper consideration of factors). Substantive reasonableness concerns whether the length of the sentence is justified. An appeal waiver can bar both kinds of challenges.
28 U.S.C. § 2255: A post-conviction procedure allowing a federal prisoner to challenge the conviction or sentence on constitutional or jurisdictional grounds (including ineffective assistance). It permits evidentiary hearings and fact development not available on a typical direct appeal record.
Strickland v. Washington: The two-part test for ineffective assistance: (1) counsel performed deficiently (below an objective standard of reasonableness), and (2) the deficiency prejudiced the defendant (it mattered to the outcome—often, in plea cases, whether the defendant would have pleaded differently).

Conclusion

United States v. Beatriz Toledo illustrates the Eleventh Circuit’s firm approach to plea-agreement finality: when a district court clearly explains an appeal waiver and the defendant confirms understanding under oath, the waiver will be enforced “according to [its] terms,” foreclosing routine sentencing disputes—even guideline-enhancement and reasonableness arguments. At the same time, the decision reaffirms that ineffective-assistance claims—especially those implicating the guilty plea—are ordinarily not resolved on direct appeal without a developed record, and instead belong in a § 2255 proceeding under Strickland v. Washington.