United States v. Tostado: Defendants Have Standing to Appeal Rogers–Singletary Errors, and Material Oral/Written Discrepancies in Search Conditions Require Full Resentencing

1. Introduction

In United States v. Amanda Tostado (4th Cir. Mar. 31, 2026), the Fourth Circuit addressed a recurring problem in federal sentencing: a mismatch between a district court’s oral pronouncement of supervised-release conditions at sentencing and the conditions later appearing in the written judgment. The case arose after Amanda Marie Tostado pleaded guilty to two drug offenses in the Eastern District of North Carolina. At sentencing, the court announced a prison term and described certain supervised-release conditions in open court. The written judgment, entered the same day, contained mandatory, standard, and special supervised-release conditions—including a warrantless-search condition worded differently from what the judge stated in court.

The principal issues were: (1) whether the oral and written warrantless-search conditions were materially different (a “Rogers–Singletary” issue), (2) whether various government arguments (lack of objection, PSR notice, plea agreement language, harmlessness) could defeat relief, and (3) an issue the panel raised at argument: whether a defendant has Article III standing to appeal based solely on an asserted Rogers–Singletary discrepancy.

2. Summary of the Opinion

The Fourth Circuit vacated Tostado’s sentence and remanded for resentencing. The majority held:

  • A material discrepancy existed between the oral and written versions of the warrantless-search condition. The oral pronouncement permitted suspicionless searches only for “safety issues,” while the written judgment authorized suspicionless searches whenever a probation officer acted “in the lawful discharge of the officer’s supervision functions,” a broader standard.
  • Under the court’s Rogers–Singletary line, the remedy for a material discrepancy is vacatur and full resentencing, without a separate harmless-error inquiry.
  • The defendant’s failure to object at the sentencing hearing did not forfeit the claim; the claim typically arises only once the written judgment issues.
  • The match between the written judgment and the PSR’s recommended language did not cure the problem absent the district court’s express adoption of the PSR recommendations.
  • The plea agreement language stating Tostado would be bound by certain conditions “regardless of whether” orally pronounced did not render the error harmless, because sentences are imposed by courts, not contracts, and the disputed condition was not validly “imposed” if not pronounced.
  • New holding on standing: a defendant has standing to appeal alleging that the written judgment contains supervised-release conditions not orally pronounced, because until invalidated those conditions create real incentives and risks that affect the defendant’s conduct.

Judge Rushing dissented, arguing the oral pronouncement was at most ambiguous and the written judgment permissibly clarified it; the dissent also emphasized the plea agreement provision and criticized the coherence of Rogers doctrine.

3. Analysis

3.1. Precedents Cited

United States v. Rogers, 961 F.3d 291 (4th Cir. 2020)

Rogers is the foundation: “all non-mandatory conditions of supervised release must be announced at a defendant’s sentencing hearing.” It also establishes (i) the oral pronouncement is the sentence and controls over the written judgment, (ii) de novo review applies to oral/written consistency, and (iii) a defendant need not object at sentencing to preserve the issue because the discrepancy becomes apparent only after entry of judgment. In Tostado, Rogers supplies both the operative rule and the rejection of the government’s preservation argument.

United States v. Singletary, 984 F.3d 341 (4th Cir. 2021)

Singletary supplies the remedial rule: when discretionary conditions appear in the written judgment without proper oral pronouncement, the proper response is to vacate and remand for resentencing. It also characterizes the “fundamental nature of a Rogers error”: the problem is not merely clerical; it is the imposition of liberty-restricting conditions outside the defendant’s presence. The Tostado majority leans heavily on Singletary to reject attempts to treat the written judgment as authoritative or to deem the discrepancy harmless.

United States v. Bullis, 122 F.4th 107 (4th Cir. 2024)

Bullis elaborates what counts as a material discrepancy and rejects the idea that PSR recommendations bind a defendant absent adoption by the court. Tostado uses Bullis in two ways: (1) to characterize the written search condition as “substantially broader” than what was orally stated, and (2) to reject the government’s PSR-based notice/waiver theory (“nonbinding recommendations” remain nonbinding “unless and until” adopted).

United States v. Mathis, 103 F.4th 193 (4th Cir. 2024)

Mathis is cited for two key propositions: (1) the written judgment may clarify the sentence when the oral pronouncement is ambiguous; and (2) the “one rotten apple” principle—one Rogers–Singletary error requires vacatur without deciding whether additional discrepancies exist. Tostado applies Mathis to limit its merits analysis to one clear discrepancy (the search condition) while noting possible additional issues.

United States v. Cisson, 33 F.4th 185 (4th Cir. 2022)

Cisson reinforces that PSR conditions are recommendations unless adopted by the court. In Tostado it functions as a doctrinal bridge: even if the PSR and written judgment match, that alignment is not a substitute for oral pronouncement or explicit adoption.

United States v. Newby, 91 F.4th 196 (4th Cir. 2024); United States v. McLaurin, 168 F.4th 693 (4th Cir. 2026); United States v. Nji, 159 F.4th 259 (4th Cir. 2025)

These cases appear in the standing discussion and to acknowledge that Rogers arguments can fail (Nji). Newby and McLaurin are invoked for the “nullity” characterization—conditions not properly pronounced can be “legal nullities.” The dissent highlights tension between “nullity” language and the majority’s practical-injury rationale for standing; the majority answers by distinguishing what is true after success on appeal from what is at stake before adjudication.

Standing and Article III precedents: Virginia House of Delegates v. Bethune-Hill, 587 U.S. 658 (2019); King v. Youngkin, 122 F.4th 539 (4th Cir. 2024); Ex parte Young, 209 U.S. 123 (1908); Food & Drug Admin. v. Alliance for Hippocratic Med., 602 U.S. 367 (2024)

The majority’s most explicitly “new” work is jurisdictional. It relies on:

  • Virginia House of Delegates v. Bethune-Hill for the court’s obligation to assure itself of jurisdiction (including standing).
  • King v. Youngkin for the caution not to confuse merits strength/weakness with standing.
  • Ex parte Young by analogy: one may challenge a coercive legal regime without first violating it.
  • Food & Drug Admin. v. Alliance for Hippocratic Med. for the proposition that standing is easier where a rule “requires or forbids” action.

Using these, the majority holds that the presence of a contested condition in a written judgment exerts practical coercion and risk sufficient for standing, even if the defendant argues that condition was never validly imposed.

3.2. Legal Reasoning

(a) The core Rogers principle: oral pronouncement controls

The majority sharply rejects the government’s framing that “a district court’s written judgment should reflect its in-court pronouncement.” In the majority’s view, the rule is stronger: the in-court pronouncement is the sentence, and any “contrary or additional” written language is ineffective. This matters because it forecloses “fixing” sentencing defects by appealing to what the written judgment says should have happened.

(b) Material discrepancy analysis applied to the search condition

The warrantless-search condition is treated as paradigmatically material because it governs when the supervisee may be searched—conduct implicating the Fourth Amendment. The oral condition allowed suspicionless searches only for “safety issues” (the only such basis the judge identified), whereas the written condition allowed suspicionless searches whenever conducted by a probation officer in the “lawful discharge” of supervisory functions. The majority reasons that “lawful supervision functions” are broader than safety (citing 18 U.S.C. § 3603(3) to illustrate the breadth of supervisory authority), so the written judgment expanded the liberty restriction beyond what was announced.

The government argued the phrase “for example” signaled that safety was merely one illustration, not a limit. The majority’s response is structural: even if “for example” makes the oral pronouncement less limiting, it does not supply any other basis for suspicionless searches. Thus, the written judgment still adds constraints on liberty that were not announced in the defendant’s presence—precisely what Rogers forbids.

(c) Rejection of procedural and “notice” workarounds

  • No contemporaneous objection required: Under Rogers, the claim arises after judgment, so failure to object during oral pronouncement does not waive it.
  • PSR alignment does not cure: PSR language is only a recommendation unless the judge adopts it. Bullis and Cisson foreclose the government’s PSR-based theory.

(d) Plea agreement and harmlessness

The government argued the discrepancy was harmless in light of plea language by which Tostado purportedly agreed to be bound by certain supervised-release conditions “regardless of whether” they were orally pronounced. The majority declines to treat that as harmlessness for three reasons:

  1. No Fourth Circuit case has found a Rogers–Singletary error harmless; the published cases uniformly vacate and remand without a separate harmlessness inquiry.
  2. Courts impose sentences; this was not a Rule 11(c)(1)(C) agreement that binds the court to a particular sentence upon acceptance.
  3. The majority treats the issue as conceptual: if a condition is not orally pronounced, then under Rogers–Singletary it is not “imposed” and therefore not validly “included” as a sentencing term—making contractual language an insufficient substitute for a lawful sentencing procedure.

Notably, the majority avoids resolving a broader waiver question: whether a defendant can waive via plea agreement the Rule 43-based right “to be present when ... sentenced.”

(e) The opinion’s distinct jurisdictional holding: standing exists

The majority’s standing holding is doctrinally important because it anticipates an argument that, if unannounced conditions are “nullities,” the defendant suffers no injury from their inclusion in the written judgment and thus cannot appeal. The court rejects that logic as premature: “nullity” is the conclusion after the defendant wins. Before resolution, the written judgment presents a real-world coercive constraint: supervisees face uncertainty, risk of enforcement, and incentives to comply to avoid reincarceration or violation proceedings. That practical restraint is sufficient injury for Article III standing.

3.3. Impact

(1) Strengthening enforceability of oral-pronouncement discipline

Tostado reinforces that district courts must ensure supervised-release conditions—especially discretionary and liberty-restricting ones—are correctly announced in open court (or validly incorporated under existing law) and that the written judgment does not broaden them. Given the court’s emphasis on the Fourth Amendment sensitivity of search conditions, the decision invites heightened caution in drafting and pronouncing such conditions.

(2) Standing holding reduces jurisdictional uncertainty in Rogers appeals

The explicit standing holding is likely to be cited to preempt future jurisdictional objections (including sua sponte concerns) in Rogers–Singletary appeals. It frames the injury as the practical coercion of a written judgment that “requires or forbids” action and exposes the defendant to risk. That analysis may also be invoked in other sentencing contexts where written judgments contain arguably unauthorized restraints.

(3) Pressure point: continued tension in “nullity” doctrine

The dissent underscores an internal stress in Fourth Circuit doctrine: calling unannounced conditions “nullities” while also describing them as practically binding enough to injure. The majority attempts to reconcile this temporally (injury before adjudication; nullity after success), but the debate signals continued intra-circuit disagreement—potentially teeing up en banc review or Supreme Court interest, especially on remedy (full resentencing vs. limited correction) and on how “nullity” interacts with revocation proceedings.

4. Complex Concepts Simplified

  • Supervised release: a period after prison when a defendant must comply with court-ordered conditions; violations can lead to reincarceration.
  • Oral pronouncement vs. written judgment: the judge must state the sentence in court; the written judgment is the later document memorializing it. In the Fourth Circuit’s Rogers line, the oral pronouncement controls for discretionary conditions.
  • Discretionary vs. mandatory conditions: mandatory conditions are imposed by statute; discretionary conditions are chosen by the judge and must be announced.
  • Reasonable suspicion: a factual basis—less than probable cause—justifying certain searches; suspicionless searches are more intrusive and more legally sensitive.
  • Material discrepancy: a difference that meaningfully changes the defendant’s obligations or liberty—e.g., expanding when searches may occur.
  • Standing: the constitutional requirement that the appellant has a concrete stake in the dispute; here, the court found the written condition’s coercive effect is enough.
  • Vacated and remanded for resentencing: the sentence is set aside and the district court must conduct a new sentencing proceeding.

5. Conclusion

United States v. Tostado does two major things. First, it applies and strengthens the Fourth Circuit’s Rogers–Singletary framework by holding that a supervised-release warrantless-search condition in a written judgment materially conflicted with the oral pronouncement and therefore required vacatur and full resentencing. Second, it adds an important jurisdictional clarification: a defendant has standing to appeal a written judgment containing conditions allegedly not pronounced in open court, because such conditions exert practical coercion and create real risk until a court rules. The case thus both tightens sentencing-procedure compliance and shores up the appellate pathway for challenging unannounced supervised-release conditions.