Pinilla Perez v. Bondi: “Reasonable Diligence” Does Not Require Pre-Change Monitoring, and the BIA Must Give a Circumstance-Specific Explanation When Denying Equitable Tolling

1. Introduction

In Pinilla Perez v. Bondi (2d Cir. Feb. 5, 2026), the Second Circuit addressed how the “reasonable diligence” requirement for equitable tolling applies when a noncitizen has already been removed and later seeks to reopen removal proceedings based on favorable changes in law.

The petitioner, Leonel Pinilla Perez, a Panamanian national and lawful permanent resident since 1990, was removed in 2011 following New York drug convictions: a 1993 guilty plea to attempted sale of cocaine (N.Y. Penal Law § 220.39(1)) and several marijuana possession misdemeanors between 2000 and 2009 (N.Y. Penal Law § 221.10 (2018)). After his removal, New York amended its marijuana laws (including repeal and mechanisms for vacatur), and later federal case law (notably United States v. Minter) undermined the categorical removability of New York cocaine offenses.

The key issue was not whether Pinilla ultimately qualified for relief, but whether the Board of Immigration Appeals (“BIA”) adequately justified its conclusion that he lacked “reasonable diligence” and thus could not equitably toll the 90-day deadline for filing an otherwise untimely and number-barred motion to reopen.

2. Summary of the Opinion

The Second Circuit granted Pinilla’s petition for review of the BIA’s denial of reopening (No. 23-6363) and remanded, holding that the BIA provided insufficient reasons for finding a lack of diligence. The Court dismissed as moot the petition challenging the BIA’s denial of reconsideration (No. 24-3151).

Critically, the Court announced two related principles:

  • No pre-change duty: reasonable diligence does not require a removed noncitizen to take steps toward reopening based on an intervening change in law before the change occurs.
  • No conclusory “time elapsed” analysis: the BIA may not deny equitable tolling using a thin, per se temporal measure (e.g., “you waited two years”) without a circumstance-specific explanation that permits meaningful judicial review.

The Court did not decide whether a change in law can qualify as an “extraordinary circumstance” for equitable tolling, because the BIA had denied tolling solely on diligence grounds.

3. Analysis

3.1. Precedents Cited

Equitable tolling framework and reviewability

  • Garcia Pinach v. Bondi, 147 F.4th 117 (2d Cir. 2025): supplied the governing two-part tolling test—(1) “extraordinary” circumstances preventing timely filing, and (2) “reasonable diligence” through the tolled period—and the abuse-of-discretion framework for reviewing the BIA’s tolling denial. The Court also invoked Garcia Pinach for the requirement that the BIA’s reasoning meet a minimum level of analysis to make judicial review meaningful.
  • Guerrero- Lasprilla v. Barr, 589 U.S. 221 (2020): supported jurisdiction, treating the application of equitable tolling standards (including diligence) as a “question of law” reviewable under 8 U.S.C. § 1252(a)(2)(D).
  • Juras v. Garland, 21 F.4th 53 (2d Cir. 2021): reinforced that jurisdictional bars apply in the motion-to-reopen context, with review limited to constitutional claims and questions of law.
  • Castellanos-Ventura v. Garland, 118 F.4th 250 (2d Cir. 2024) and Poradisova v. Gonzales, 420 F.3d 70 (2d Cir. 2005): grounded the principle that agency decisions “stand or fall” on the reasons given, and that conclusory statements are inadequate.

Defining the “tolled period” and “reasonable diligence”

  • Rashid v. Mukasey, 533 F.3d 127 (2d Cir. 2008): provided the “entire period he seeks to toll” concept. Although Rashid arose in ineffective-assistance claims, the Court extended its structure to change-in-law tolling, while rejecting any reading that would require action before the legal basis for relief exists.
  • Wang v. Bd. of Immigr. Appeals, 508 F.3d 710 (2d Cir. 2007): cautioned against rigid, per se timing rules in equitable tolling assessments.
  • Baldayaque v. United States, 338 F.3d 145 (2d Cir. 2003): contributed the equitable benchmark—whether the person acted as diligently as could reasonably be expected under the circumstances (not an “extreme diligence” requirement).
  • Doe v. United States, 76 F.4th 64 (2d Cir. 2023) and Clark v. Hanley, 89 F.4th 78 (2d Cir. 2023): reinforced that diligence is “reasonable,” not “maximum feasible,” and that equitable tolling is circumstance-sensitive.
  • Holland v. Florida, 560 U.S. 631 (2010): the Supreme Court source for “reasonable diligence” and the equity-driven rejection of mechanical rules.

Change-in-law diligence for removed noncitizens (persuasive authorities)

  • Williams v. Garland, 59 F.4th 620 (4th Cir. 2023): heavily relied upon for the proposition that a person cannot be expected to pursue “rights” that the law does not yet recognize; also used to reject “in a vacuum” expectations like contacting X attorneys or asking family members to monitor immigration law.
  • Bracey v. Superintendent Rockview SCI, 986 F.3d 274 (3d Cir. 2021): supplied the practical lens—focus on reasonable expectations “in the petitioner’s position,” including that one need not “continuously monitor public sources for years.”
  • Lugo-Resendez v. Lynch, 831 F.3d 337 (5th Cir. 2016): contributed equity’s animating purpose (avoiding “archaic rigidity”) and the recognition that removed noncitizens often face poverty, limited education, language barriers, and difficulty tracking U.S. law—context that bears directly on what diligence is “reasonable.”
  • Pervaiz v. Gonzales, 405 F.3d 488 (7th Cir. 2005): used for the key corrective: the test is not the length of delay, but whether the claimant could reasonably have been expected to file earlier.
  • Goulart v. Garland, 18 F.4th 653 (9th Cir. 2021) (Korman, J., dissenting): cited as additional support for contextual diligence analysis.

Substantive immigration/criminal-law background

  • United States v. Minter, 80 F.4th 406 (2d Cir. 2023): confirmed New York’s definition of cocaine is categorically broader than the federal definition, undercutting removability based on Pinilla’s 1993 cocaine conviction. The Government conceded that if reopened, that conviction would no longer support removal.
  • I.N.S. v. St. Cyr, 533 U.S. 289 (2001): referenced in discussing former INA § 212(c) relief; the Court found it unnecessary to reach discretionary relief issues given the Government’s concession on removability if reopened.
  • Watson v. United States, 865 F.3d 123 (2d Cir. 2017): distinguished in a footnote—while lack of education/pro se status may not establish “extraordinary circumstances,” those facts may still be relevant to the diligence inquiry.

3.2. Legal Reasoning

  1. Jurisdiction and standard of review: Although criminal-removal jurisdictional bars limit review, the Court held it could review the diligence determination as a legal question under Guerrero- Lasprilla v. Barr.
  2. Equitable tolling elements: The Court reiterated the two-part framework from Garcia Pinach v. Bondi but confined its decision to diligence because the BIA had not resolved whether change in law is an “extraordinary circumstance.”
  3. Defining the relevant diligence window: Using Rashid v. Mukasey’s “entire period sought to be tolled” concept, the Court clarified that—when the asserted basis is a change in law—diligence cannot sensibly require action before that change occurs.
  4. What “reasonable diligence” means post-removal: Grounded in Holland v. Florida, Doe v. United States, and the out-of-circuit change-in-law cases, the Court emphasized a realistic, position-sensitive inquiry. It provided a non-exhaustive set of factors the BIA should consider, including:
    • capacity to learn of and act on the change (e.g., removal abroad, detention, poverty, language barriers, access to legal information);
    • reasonable investigative steps (e.g., reconnecting with prior counsel or seeking new counsel);
    • reasonable promptness after discovery of the change.
  5. Why the BIA’s explanation failed: The BIA effectively relied on a single observation—Pinilla waited “approximately 2 years” after the marijuana-law revisions—without explaining what diligence it expected of a removed person in Panama, what circumstances it credited or rejected, or why earlier filing was reasonably expected. Under Garcia Pinach v. Bondi, Poradisova v. Gonzales, and Pervaiz v. Gonzales, that level of analysis was too conclusory to survive review.

3.3. Impact

  • Constrains categorical “delay-based” denials: The opinion signals that the BIA cannot treat elapsed time as dispositive without explaining why earlier action was reasonably expected in the noncitizen’s real circumstances.
  • Clarifies diligence expectations for removed applicants: By rejecting a duty to monitor legal developments pre-change, the Court reduces the risk that equitable tolling becomes illusory for removed persons who lack resources to track U.S. doctrine.
  • Likely procedural remands, not merits rulings: Because the Court focused on adequacy of agency reasoning, future litigation will likely center on the quality of the BIA’s diligence analysis and record development (e.g., evidence of access barriers, efforts to obtain counsel, and timing of discovery), rather than purely on calendar math.
  • Open question preserved: The Court expressly left unresolved whether a change in law is an “extraordinary circumstance,” ensuring continued doctrinal development on tolling’s first prong in future cases.

4. Complex Concepts Simplified

  • Motion to reopen: a request to restart concluded removal proceedings to consider new facts or new legal grounds.
  • 90-day deadline and “number-bar”: federal law generally allows only limited reopening requests, and usually requires filing within 90 days of the final BIA order (8 U.S.C. § 1229a(c)(7)(C)(i)).
  • Equitable tolling: a fairness doctrine that pauses a filing deadline when extraordinary circumstances prevented timely filing and the party acted with reasonable diligence.
  • Reasonable diligence: not the most aggressive possible effort, but what a reasonable person in the petitioner’s circumstances could be expected to do.
  • Categorical removability / “categorically broader”: a conviction triggers immigration consequences only if the elements of the state offense match (or are narrower than) the federal definition; if state law covers more conduct/substances, it may not categorically qualify.
  • Vacatur: a court order setting aside a conviction. (The opinion notes a likely scrivener’s error in Pinilla’s vacatur documents citing the wrong statutory subsection.)
  • Sua sponte reopening: discretionary reopening initiated by the agency on its own; the Court did not reach this issue because it remanded on the inadequate diligence analysis.

5. Conclusion

Pinilla Perez v. Bondi strengthens equitable tolling doctrine in the motion-to-reopen context by insisting that “reasonable diligence” be assessed through a realistic, removed-person lens and by rejecting any implied requirement that a noncitizen anticipate and act on legal changes before they occur. Just as importantly, the decision reinforces administrative-law fundamentals: when the BIA denies tolling, it must articulate a fact-sensitive rationale that explains why earlier filing was reasonably expected, rather than relying on a conclusory measure of elapsed time. On remand, the BIA must reassess diligence under these principles, while the broader question—whether change in law itself is an “extraordinary circumstance”—remains open for future cases.