Finality First: Second-in-Time §2255 Filings During a Pending Appeal Are “Second or Successive”; District Courts Must Consider §3553(a) When Asked to Modify Supervised-Release Conditions

Finality First: Second-in-Time §2255 Filings During a Pending Appeal Are “Second or Successive”; District Courts Must Consider §3553(a) When Asked to Modify Supervised-Release Conditions

Introduction

In United States v. Ephren Taylor, II, No. 20-11238 (11th Cir. Sept. 10, 2025), the Eleventh Circuit reaffirmed the primacy of finality in federal habeas proceedings and clarified procedural boundaries for post-judgment filings under the Antiterrorism and Effective Death Penalty Act (AEDPA). Against the backdrop of an unusually tangled post-conviction record—spanning a guilty plea to a large-scale investment-fraud scheme, an initial §2255 motion, multiple post-judgment motions, two district judges, and three appeals—the Court addressed two core questions:

  • When is a later-in-time filing in a habeas case “second or successive” under AEDPA’s gatekeeping regime when an appeal from the first petition is still pending?
  • What must a district court do when a defendant moves under 18 U.S.C. §3583(e)(2) to modify the conditions of supervised release?

The Court, drawing on the Supreme Court’s intervening decision in Rivers v. Guerrero, 605 U.S. 443 (2025), held that once a district court enters a final merits judgment on an initial habeas application, later-in-time filings that assert new habeas claims are generally “second or successive” even if the first appeal remains pending—unless the filing is a timely Rule 59(e) motion. At the same time, the Court vacated the denial of Taylor’s motion to modify his supervised-release conditions because the district court did not demonstrate that it considered the statutorily required 18 U.S.C. §3553(a) factors.

Summary of the Opinion

The Eleventh Circuit:

  • Affirmed the district court’s dismissal of multiple pro se filings—including Rule 60(b) and “reopen/supplement/amend” motions—as unauthorized “second or successive” §2255 applications barred by 28 U.S.C. §2244(b), and alternatively outside the district court’s jurisdiction while an appeal was pending.
  • Held that a limited remand confined to the question of a certificate of appealability (COA) does not expand the district court’s jurisdiction to entertain new habeas claims or amendments.
  • Vacated the denial of Taylor’s motion to modify supervised-release conditions under §3583(e)(2), and remanded because the district court failed to show meaningful consideration of the §3553(a) factors, which include the Sentencing Commission’s policy statements.

The result: affirmed in part, vacated in part, and remanded.

Background

Ephren Taylor, formerly CEO of City Capital Corporation, promoted fraudulent investments—often targeted to African American and Christian communities via a “Building Wealth Tour”—and ran what authorities described as a Ponzi scheme. He pleaded guilty in 2014 to one count of conspiracy to commit wire and mail fraud (18 U.S.C. §§1341, 1349) and received a 235-month sentence, later reduced to 223 months, plus three years’ supervised release and over $15.5 million in restitution.

In 2016, Taylor filed a pro se §2255 motion asserting ineffective assistance of counsel and sentencing errors. The district court denied relief in March 2019 (adopting a magistrate judge’s report and recommendation after de novo review). Taylor then filed a timely Rule 59(e) motion, a notice of appeal, and later a Rule 60(b) motion. During a limited remand for the district court to address a COA, Taylor lodged a flurry of additional motions—including to supplement and amend his §2255 petition and to modify conditions of supervised release. The district court denied most motions and declined a COA. After the Eleventh Circuit denied a COA in the parallel appeal, Taylor pursued this appeal from the denial of the “reopen/supplement/amend” filings and the denial of his motion to modify supervised release.

Analysis

Precedents Cited and Their Influence

  • Rivers v. Guerrero, 605 U.S. 443 (2025): The Supreme Court resolved a circuit split and held that “once the judgment has been entered with respect to the initial habeas petition, a second-in-time filing that makes new habeas claims generally qualifies as a second or successive petition,” even if an appeal is pending. The Court distinguished timely Rule 59(e) motions—which suspend finality and are not “second or successive”—from Rule 60(b) motions, which attack an extant judgment. The Court acknowledged district courts cannot grant Rule 15 amendments while the case is on appeal, though petitioners may seek an indicative ruling under Rule 62.1; Rivers had not done so. The Eleventh Circuit relied on Rivers to conclude Taylor’s later-in-time habeas filings were barred as “second or successive.”
  • Boyd v. Secretary, Dep’t of Corrections, 114 F.4th 1232 (11th Cir. 2024): Before Rivers, the Eleventh Circuit held that after entry of final judgment, Rule 15 amendments are unavailable unless the judgment is first set aside, and attempts to add new claims in separate filings are governed by §2244(b)’s gatekeeping. Boyd also underscored that an appeal divests the district court of jurisdiction over aspects of the case on appeal. Boyd’s framework dovetails with Rivers and supports the Eleventh Circuit’s disposition here.
  • Banister v. Davis, 590 U.S. 504 (2020): Clarified that timely Rule 59(e) motions are part of a single, ongoing habeas proceeding and not “second or successive.” The Eleventh Circuit applied this distinction to explain why Taylor’s later Rule 60(b) and amendment-style filings did not enjoy Rule 59(e)’s protection.
  • Gonzalez v. Crosby, 545 U.S. 524 (2005): Defined “claim” in the §2244(b) context as an asserted federal basis for relief from a conviction; Rule 60(b) motions that present such claims are treated as successive applications. This definition informed the Court’s classification of Taylor’s later filings.
  • Magwood v. Patterson, 561 U.S. 320 (2010) and Wilkinson v. Dotson, 544 U.S. 74 (2005): Emphasized that habeas petitions “seek invalidation” of the judgment authorizing confinement, reinforcing why Taylor’s new allegations (e.g., uncommunicated plea offer, alleged government misrepresentations) qualified as successive claims.
  • United States v. Cordero, 7 F.4th 1058 (11th Cir. 2021): Held that §3583(e)(2) is not a vehicle to collaterally attack the legality of supervised-release conditions—that must be done on direct appeal or through §2255. Cordero also explained that §3583(e) directs courts to consider specified §3553(a) factors when deciding modification requests. Cordero supplied the governing framework for Taylor’s modification motion—and the reason the Eleventh Circuit vacated for lack of §3553(a) analysis.
  • Johnson, 877 F.3d 993 (11th Cir. 2017) and Douglas, 576 F.3d 1216 (11th Cir. 2009): Establish that, while a court need not march through each §3553(a) factor, the record must show the pertinent factors were considered and provide enough for meaningful appellate review.
  • Standards and jurisdiction cases: Stewart v. United States, 646 F.3d 856 (11th Cir. 2011) (de novo review of successive characterization); Zakrzewski v. McDonough, 490 F.3d 1264 (11th Cir. 2007) (de novo on jurisdiction); Davenport v. United States, 217 F.3d 1341 (11th Cir. 2000) (abuse-of-discretion for leave-to-amend rulings); United States v. Diveroli, 729 F.3d 1339 (11th Cir. 2013) (divestiture upon notice of appeal); and Bravo v. United States, 532 F.3d 1154 (11th Cir. 2008) (alternative holdings are binding).
  • Sister-circuit decisions contextualized: United States v. Santarelli, 929 F.3d 95 (3d Cir. 2019) and Whab v. United States, 408 F.3d 116 (2d Cir. 2005) (some circuits hold second-in-time filings in abeyance while the first appeal is pending). Rivers acknowledged this practice but did not mandate it; the Eleventh Circuit endorsed district-court discretion not to hold such motions in abeyance.

Legal Reasoning

1) The habeas “second or successive” classification and jurisdiction

The Court began from AEDPA’s core concern: finality. Under 28 U.S.C. §2244(b) and §2255(h), once a district court has entered final judgment on a first-in-time habeas application, a later filing that asserts new claims is generally “second or successive” and cannot proceed absent authorization from the court of appeals. The doctrinal hinge is final judgment, not the pendency of an appeal.

Applying Rivers and Boyd, the Eleventh Circuit held that:

  • Entry of final judgment on Taylor’s initial §2255 motion occurred when the district court adopted the R&R on March 6, 2019, and, after the court disposed of his timely Rule 59(e) motion on April 11, 2019, finality reattached. Post-judgment filings thereafter—especially the Rule 60(b) motion and the “reopen/supplement/amend” filings—sought to add new habeas claims (e.g., failure to communicate a plea offer; alleged government misrepresentations) and thus qualified as “second or successive.”
  • A notice of appeal divested the district court of jurisdiction over “aspects of the case involved in the appeal.” The limited remand returned jurisdiction solely to decide whether to issue a COA; it did not authorize the court to entertain new claims, amendments, or collateral requests. Taylor’s attempt to “hijack” the limited remand by filing a raft of motions fell outside the remand’s scope and the court’s jurisdiction.
  • Even construing Taylor’s “supplement/amend” filing as a Rule 15 motion, Rivers and Boyd confirm a district court cannot grant a Rule 15 amendment after entry of final judgment and while an appeal is pending; at most, a court could hold such a motion in abeyance or issue an indicative ruling under Rule 62.1. Here, the district court acted within its discretion to treat the motion as successive rather than hold it in abeyance, citing efficiency and the risk of piecemeal litigation.

The Court emphasized that only a timely Rule 59(e) motion suspends finality and avoids “second or successive” classification; a Rule 60(b) motion does not.

2) The supervised-release modification motion

Turning to §3583(e)(2), the Court agreed with the district court that Taylor’s challenges to the legality or constitutionality of his conditions of supervised release were not properly raised in a §3583(e) motion. Under Cordero, such attacks must be pursued on direct appeal or via §2255; §3583(e)(2) is not a vehicle for collateral attacks on a sentence.

But the Court vacated because the district court failed to show it considered the §3553(a) factors when denying Taylor’s request to modify his conditions. Section 3583(e)(2) expressly requires consideration of enumerated §3553(a) factors, including “any pertinent policy statements” of the Sentencing Commission—precisely the ground Taylor invoked when he pointed to clarifying amendments to supervised-release conditions in the Guidelines. The district court did not solicit a government response, did not identify any considered factors, and left no record for meaningful appellate review. That omission constituted an abuse of discretion.

Impact

AEDPA practice and post-judgment strategy

  • Final judgment is the line that matters. After final judgment on a first habeas application, any second-in-time filing asserting new claims is usually “second or successive,” even while the appeal is pending. Petitioners must seek preauthorization under §2244(b)/§2255(h) and satisfy one of the narrow gateways: a new, retroactively applicable rule of constitutional law from the Supreme Court or newly discovered facts establishing actual innocence by clear and convincing evidence.
  • Timing and vehicle selection are crucial. If a party needs to correct or supplement the record post-judgment, a timely Rule 59(e) motion (within 28 days) preserves the “single proceeding” character and avoids successive classification. Later Rule 60(b) motions commonly will be treated as successive if they assert or reassert claims.
  • Know the tools and their limits during an appeal. A district court cannot grant Rule 15 amendments while the case is on appeal. Parties may:
    • Seek an indicative ruling under Fed. R. Civ. P. 62.1 in the district court, and then ask the court of appeals for a limited remand; or
    • Request that the district court or the court of appeals hold a second-in-time motion in abeyance pending resolution of the first appeal. Rivers acknowledges the practice but does not require it; district courts retain discretion and may deny abeyance to prevent piecemeal litigation.
  • Limited remands are just that—limited. A remand solely to decide a COA does not open the district court’s door to new filings or amendments. Practitioners should obtain explicit remand authority for any additional action sought.

Supervised-release litigation

  • Two distinct tracks:
    • Legality/constitutionality challenges to conditions belong on direct appeal or in a §2255 motion.
    • Modification requests under §3583(e)(2) are permissible and must be evaluated against the §3553(a) factors. Courts should create a record demonstrating consideration of the pertinent factors, including Sentencing Commission policy statements and any relevant clarifying amendments to supervised-release conditions.
  • Process matters. Orders denying modification should reflect an individualized assessment. While courts need not recite each §3553(a) factor, the record must allow meaningful appellate review.

Complex Concepts Simplified

  • “Second or successive” habeas application: A later filing that asserts a new federal ground for relief from a conviction after a court has entered final judgment on a prior habeas application. Such filings require preauthorization from the court of appeals and must meet stringent statutory gateways.
  • Finality: The point at which a judgment is no longer subject to change in the district court. A timely Rule 59(e) motion pauses finality; a Rule 60(b) motion does not. Once finality attaches, new filings are typically treated as successive.
  • Rule 59(e) vs. Rule 60(b):
    • Rule 59(e) (within 28 days): part of the same proceeding; not “second or successive.”
    • Rule 60(b): seeks to disturb an existing judgment; if it asserts claims, it will usually be treated as successive under AEDPA.
  • Rule 15 (amendments) during appeal: The district court cannot grant amendments once final judgment has entered and the case is on appeal. A party may seek an indicative ruling (Rule 62.1) and a remand, or ask a court to hold the matter in abeyance (discretionary).
  • Limited remand: An appeal court may return a case to the district court for a narrow purpose (e.g., decide a COA). The district court may act only within that scope.
  • §3583(e)(2) modifications: A mechanism to change supervised-release conditions based on considerations set out in §3553(a) (e.g., defendant’s history, deterrence, public protection, and relevant Sentencing Commission policy statements). Not a route to challenge the legality of the original sentence or conditions.
  • Certificate of appealability (COA): A jurisdictional prerequisite for appealing the denial of habeas relief. The district court should decide it; if not, the court of appeals may issue a limited remand for that purpose.

Conclusion

United States v. Taylor distills and applies a now-settled rule from Rivers v. Guerrero: finality is the touchstone for AEDPA’s “second or successive” inquiry. Once the district court has entered a final merits judgment on an initial habeas filing (and any timely Rule 59(e) motion has been resolved), later-in-time filings that seek to add claims are generally successive even if the first appeal is still pending. Limited remands do not relax this jurisdictional boundary. Petitioners seeking to introduce new matters after final judgment must proceed through §2244(b)/§2255(h)’s narrow gateways or use the proper procedural tools (indicative rulings, targeted remands) in a timely way.

On supervised release, the decision delivers an important procedural reminder: while §3583(e)(2) cannot be used to collaterally attack the legality of conditions, district courts must nonetheless weigh the §3553(a) factors when deciding whether to modify conditions, including consideration of applicable Sentencing Commission policy statements. The failure to make a record of that consideration warrants vacatur and remand.

The case thus reinforces AEDPA’s demand for orderly, single-pass federal collateral review while ensuring that the statutory framework governing supervised-release modifications is scrupulously applied. For litigants, the message is clear: choose the right vehicle at the right time, and build a record that permits meaningful appellate review.

Case Details

Year: 2025
Court: Court of Appeals for the Eleventh Circuit

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