First Circuit Conditions Internet-Monitoring Fees on Ability-to-Pay and Clarifies Limits on Ex Parte Sentencing Inputs

Introduction

This appeal from a supervised-release revocation raises recurring—and increasingly salient—questions at the intersection of technology, due process at revocation, and the constitutional boundaries of supervision conditions. The First Circuit affirms the district court’s second revocation and sentence for Alexis Negrón-Cruz, a defendant convicted of a child-pornography offense whose supervised release had been revoked multiple times.

Two issues dominated the appeal: (1) whether the district court improperly relied on ex parte communications with a probation officer to find violations and sentence the defendant; and (2) whether two “internet monitoring” conditions—requiring the defendant to use only devices with court-approved monitoring software and to pay associated costs based on his ability to pay—are unconstitutional or unlawfully delegate judicial power to the Probation Office.

The decision clarifies the First Circuit’s ex parte framework: while judges may confer with probation officers for advice, they may not materially rely at sentencing on “new and significant” facts communicated ex parte unless disclosed and tested. Applying that rule, the court finds one ex parte reliance to be harmless and another not “new” because it was in the public record. On the conditions, the court holds that monitoring-only internet restrictions are facially valid; that any First Amendment or equal-protection attacks premised on implementation delays or inability-to-pay are unripe as-applied claims; and that enforcement of monitoring fees must conform to Bearden’s ability-to-pay principles. The court also rejects an unlawful-delegation challenge and explains how supervisees can seek relief under 18 U.S.C. § 3583(e)(2).

Summary of the Judgment

• Jurisdiction and mootness: The appeal from the Second Revocation is not moot despite a subsequent Third Revocation because the defendant remains under supervised release and could obtain equitable relief affecting the length or conditions of ongoing supervision (citing Reyes-Barreto).
• Ex parte communications:
  • Judges may consult probation for advice/analysis. However, it is error to rely ex parte on “new and significant” facts not in the record.
  • The court assumed an ex parte conversation occurred, but held: (a) the “backup phone” fact was not “new” because it was alleged in a filed arrest-warrant motion and went uncontested; (b) the “Uber lie” fact was “new and significant,” so reliance was error, but harmless given other, unchallenged violations that supported revocation and the sentence.
• Internet conditions (Special Conditions 31 and 32):
  • Facially valid: Monitoring conditions are permissible and not a total internet ban. The “ability to pay” clause does not violate equal protection on its face.
  • As-applied challenges unripe: Claims that the Probation Office’s implementation (e.g., a 20-day delay to install software or financial burden) produced excessive speech restrictions or violated Bearden are fact-dependent and must be raised when and if the facts are developed.
  • Ability-to-pay guidance: The court reiterates that enforcement must honor Bearden: probation cannot require payment or cut off internet access for nonpayment absent a finding of ability to pay and willful refusal to do so.
• Delegation: No improper delegation. Probation’s temporary suspension of the monitoring requirement (inconsistent with the condition) did not mean the condition delegated authority to decide whether monitoring would apply. The contractual CIMP program was not enforced and any challenge to its particulars is unripe.
• Disposition: Second Revocation judgment and sentence affirmed in full. Requests for access to a mental health report and reassignment to a different judge denied (no reviewable order and no reversible error).

Factual and Procedural Background

After a 2013 guilty plea to possessing child pornography—conduct that included sharing sexual videos involving minors and attempting to arrange sex with a child—Negrón received 10 years’ prison plus 25 years’ supervised release. Upon starting supervision in December 2019, he faced conditions restricting internet-capable devices without probation’s approval. The First Revocation (February 2022) followed unauthorized internet access; the district court imposed new conditions:

• Special Condition 31: Consent to installation of monitoring/filtering systems; unannounced exams; contribution to the cost “based on his ability to pay.”
• Special Condition 32: No possession/use of any internet-capable device except those with monitoring/filtering systems authorized by probation.

Probation initially allowed the defendant to keep a smartphone until he could afford monitoring. Over the ensuing months, probation reported that Negrón acquired a second smartphone, intermittently failed to follow instructions (e.g., provide passcodes), retained an iPad from a prior employer, and resisted surrendering devices. In early 2023, two preliminary hearings produced probable-cause findings for violations, and in March 2023 probation seized a backup smartphone on the same day it returned the primary phone with monitoring software installed (after about 20 days). At the November 2023 final revocation hearing, the court revoked, imposed “time served,” and re-imposed 270 months’ supervision with the same conditions. Negrón appealed.

While the appeal was pending, the district court revoked supervision a third time (December 2024), imposed two years’ imprisonment and 268 months’ supervision; that separate appeal remains pending. The First Circuit held the Second Revocation appeal was not moot.

Precedents Cited and How They Shaped the Decision

• Ex parte communications and sentencing record:
  • Pepper v. United States and Reyes-Correa: sentencing information is broad but not unlimited; due process requires disclosure and chance to rebut.
  • Bramley: probation officers are extensions of the court; ex parte advisory communications are usually permissible, but new, significant, adverse facts cannot be used unless disclosed and tested.
  • Ramos-Carreras: clarifies “new” (not in record) and “significant” (materially relied upon). Reliance on undisclosed ex parte facts can be reversible.
• Harmless error: Williams v. United States. Even if reliance on ex parte information is error, it is harmless if it did not affect the sentence.
• Ability to pay and equal protection:
  • Bearden v. Georgia: cannot revoke solely for nonpayment without a finding of ability to pay or willful refusal despite bona fide efforts.
  • Merric, Santarpio, Chorney: First Circuit applications of Bearden-type principles; enforcement of financial conditions requires ability-to-pay findings.
• Internet restrictions and the First Amendment:
  • Packingham: the internet is a core forum for speech; sweeping restrictions on internet access raise serious First Amendment concerns.
  • First Circuit supervision cases: Perazza-Mercado, Ramos, Hinkel, Aquino-Florenciani, Windle—consistent theme that total or near-total internet bans are disfavored, but monitoring conditions are permissible tailoring.
  • Other circuits: Eaglin (2d Cir.), Ellis (4th Cir.)—recognize the First Amendment interest; the First Circuit, however, continues to apply abuse-of-discretion review, not a “more searching” standard.
• Delegation of judicial power:
  • Morales-Cortijo, Mike, Sepulveda-Contreras: courts cannot delegate core punishment decisions; probation may perform ministerial tasks and supervise details.
  • Sebastian, Stergios, Mercado: probation may use programs like a CIMP to operationalize conditions; overreach can be corrected by seeking modification under § 3583(e)(2).
• Mootness in supervised-release appeals: Mazzillo, Reyes-Barreto, ACLU of Mass. v. USCCB—appeals are not moot if the defendant remains on supervised release and relief could alter its terms.

Legal Reasoning

1) Ex Parte Communications: Advice Is Permissible, New Facts Are Not—And Harmless Error Matters

The court reaffirmed the First Circuit’s two-step framework. Consulting probation for advice/analysis is allowed; however, reliance on ex parte communications that supply “new and significant” facts is improper unless disclosed and subjected to adversarial testing.

• “Backup smartphone” fact (March 27): Even if conveyed ex parte, it was not “new.” It appeared in a publicly filed arrest-warrant motion and went uncontested at the April preliminary hearing. Information in a filed motion is part of the record, making it “difficult to characterize” as new.
• “Uber lie” finding (January 19): The district court’s finding that Negrón lied about an Uber account activated before that date did rest on “new and significant” information obtained outside the record and was therefore error. But the error was harmless because multiple other, unchallenged lies and employment-notice failures independently supported revocation and the sentence.
• No structural error: Ex parte issues of this kind do not constitute structural error requiring automatic reversal.

2) Internet Monitoring Conditions: Facially Valid, With Bearden Safeguards

Special Conditions 31 and 32 require the defendant to:

• Use only devices that support court-authorized monitoring/filtering; and
• Pay monitoring costs “based on his ability to pay.”

The court draws a line between facial validity and as-applied challenges:

• First Amendment: Monitoring conditions are not a total or partial ban; they are a narrower, tailored alternative, repeatedly approved by the First Circuit. A 20-day gap in access during forensic examination/installation may raise as-applied concerns, but that question is fact-intensive and not ripe on the record presented.
• Equal protection/ability to pay: A condition that ties payment to “ability to pay” is facially valid. Enforcement must follow Bearden: probation cannot penalize a defendant for nonpayment without first finding an ability to pay and, where appropriate, willful refusal to pay. The court underscored that probation cannot bar internet use for nonpayment unless it determines the defendant could pay at least part of the cost and willfully refused.
• Unripe as-applied claims: Because the defense framed its constitutional objections prospectively and the record lacked concrete findings (e.g., what the paystubs showed; what a reasonable forensic timeline is), the First Circuit declined to adjudicate hypothetical or future enforcement disputes.

3) Delegation: No Transfer of Core Sentencing Power

The defendant argued that probation effectively decided “whether” monitoring applies and that a 44-paragraph CIMP contract unlawfully expanded punishment. The court rejected both.

• Monitoring requirement (Condition 32): The text vests the obligation in the court’s condition; probation’s temporary suspension of monitoring without authority did not convert the condition into an unlawful delegation. The condition itself did not give probation discretion to decide whether monitoring applies.
• CIMP contract: CIMPs are recognized implementation tools. Because the defendant never signed it and it was not enforced, challenges to specific CIMP provisions were unripe and would depend on future facts.
• Safety valve: If probation overreaches, defendants can move under § 3583(e)(2) to clarify, modify, enlarge, or reduce conditions.

4) Standard of Review and Circuit Approach

The court declined to adopt the Second Circuit’s “more searching” review for internet conditions (Eaglin), and confirmed First Circuit law: supervised-release conditions are reviewed for abuse of discretion, with fact findings for clear error and legal questions de novo. That approach has consistently been applied even where conditions implicate constitutional interests.

5) Mootness: Appeal Remains Live Despite Later Revocation

Applying Reyes-Barreto, the court held the appeal was not moot. Because the defendant remains on supervised release, relief could affect the ongoing term (for example, by supporting a motion to modify or terminate early under § 3583(e)(1)-(2)). The district court’s reliance on a “pattern of recurrent noncompliance” at the Third Revocation further linked the stakes of this appeal to future supervision.

Impact and Implications

• Ex parte practice: District judges within the First Circuit should ensure that any facts gleaned ex parte from probation are placed on the record before materially relying on them. The decision reinforces an operational rule: advice is fine; new adverse facts must be disclosed and tested. Defense counsel should object contemporaneously when ex parte facts appear to be influencing findings or sentencing.
• Technology fees and Bearden compliance: This opinion applies the Bearden framework to modern supervision technology costs. Probation officers and courts should explicitly document ability-to-pay findings before conditioning device access on payment—or before responding to nonpayment with restrictions. Clear recordkeeping will reduce litigation risk and protect indigent supervisees.
• Internet access conditions: The First Circuit continues to favor tailored monitoring over categorical bans. Courts should:
  • Draft conditions that clearly allow internet use on monitored devices and prohibit unmonitored devices;
  • Specify cost-sharing based on ability to pay and the process for making that determination;
  • Anticipate operational realities (e.g., reasonable timelines for forensic examinations/installation) and build notice/transition mechanisms into orders.
• Ripeness and as-applied litigation posture: Fact-poor, hypothetical objections to enforcement are likely to be dismissed as unripe. Supervising officers and defense counsel should build robust factual records on implementation (cost, timelines, availability of non-internet devices, employment circumstances) and bring targeted § 3583(e)(2) motions if operational burdens become excessive.
• Delegation boundaries: Conditions should preserve the court’s role in setting the punishment while authorizing probation to implement ministerial details. Written program agreements (like CIMPs) should track the condition’s scope and avoid adding punitive terms. Any inconsistency is best resolved by motion practice rather than defaulting to revocation.
• Mootness strategy: For parties litigating serial revocations, this case confirms that appeals can remain live and consequential so long as supervised release continues and later sentences rely on the pattern of violations.

Complex Concepts Simplified

• Supervised release: A post-prison period during which a person must follow court-ordered conditions, monitored by the U.S. Probation Office. Violations can lead to revocation and new sanctions.
• Revocation: When a court finds a violation of conditions, it can revoke supervised release and impose imprisonment and/or a fresh term of supervised release.
• Special vs. standard conditions: Standard conditions are routine requirements (e.g., reporting, employment, truthfulness). Special conditions are tailored to the individual (e.g., technology monitoring, treatment).
• Ex parte communication: A judge’s communication with one side without the other present. With probation officers, judges may seek advice, but may not rely on undisclosed “new and significant” facts against the defendant.
• “New and significant” facts: “New” means not already in the record; “significant” means the judge materially relied on the fact in deciding sentence. Such facts must be disclosed and subject to challenge before use.
• Harmless error: Even if the judge relied on improper information, the sentence stands if the outcome would have been the same without the error.
• Facial vs. as-applied challenges: A facial challenge attacks a rule’s validity in all applications. An as-applied challenge argues the rule is being enforced unconstitutionally under particular facts.
• Ripeness: Courts avoid judging hypothetical disputes. If an issue depends on future facts (e.g., what costs are and whether the defendant can pay), the challenge is unripe until those facts materialize.
• Bearden ability-to-pay rule: A court cannot punish a defendant for nonpayment without finding the defendant had the ability to pay and willfully refused or failed to make bona fide efforts.
• Delegation of judicial power: The court must decide punishment. Probation may handle administrative details but cannot be given authority to decide whether a punitive condition applies.
• § 3583(e)(2) modification: A statutory tool allowing the court to modify, clarify, reduce, or enlarge conditions during supervision when circumstances warrant.

Practical Guidance Going Forward

• For district courts:
  • When relying on information from probation, ensure key facts are in the filed record and give the defendant an opportunity to respond.
  • When imposing monitoring fees, make explicit ability-to-pay findings and set a process for reassessment as finances change.
  • Consider specifying reasonable timeframes for forensic exams/installation to avoid extended de facto internet bans.
• For probation offices:
  • Document ability-to-pay analyses before conditioning access on payment or responding to nonpayment.
  • Avoid suspending or reactivating court-imposed conditions without court authorization; seek clarification or modification when needed.
  • Use CIMP-type agreements to implement, not expand, conditions; flag ambiguities (e.g., limits on number of devices) for court guidance.
• For defense counsel:
  • Object promptly if ex parte facts appear to influence sentencing; seek disclosure and an opportunity to rebut.
  • Develop a record on employment, income, and costs; if the client cannot pay, move for findings and appropriate adjustments under § 3583(e)(2).
  • If installation or forensic delays effectively bar internet access, gather evidence on necessity and reasonableness and seek tailored relief.

Conclusion

United States v. Negrón-Cruz refines the First Circuit’s supervisory-release jurisprudence in two important respects. First, it crisply enforces the boundary on ex parte communications: advisory contacts with probation are permissible, but undisclosed “new and significant” facts cannot ground sentencing—subject to harmless-error analysis. Second, it integrates classic Bearden ability-to-pay protections into the modern context of technology monitoring, confirming that payment-based internet access restrictions must rest on findings of actual ability to pay and willful refusal.

The court’s constitutional analysis underscores a stable through-line in First Circuit law: monitoring obligations are a permissible, narrowly tailored alternative to broad internet bans, but their implementation must be reasonable and rooted in a factual record. As-applied challenges will ripen when facts develop; until then, § 3583(e)(2) remains the primary vehicle to modify, clarify, or correct supervision in real time.

In an era where digital access is both ubiquitous and fraught for certain supervisees, this decision offers practical guardrails for courts and probation, and concrete avenues for supervisees to protect constitutional and financial interests without compromising public safety or the integrity of supervision.