Ruling: The court AFFIRMED the District Court's judgment on all issues.
Reasoning:
Electronic Search Condition: The court held the condition was procedurally and substantively reasonable. Although the District Court's initial explanation referencing "customary practice" was inadequate, the transcript revealed an appropriately individualized assessment based on Jimenez's lengthy criminal record, crimes of violence, extensive drug trafficking involvement, disciplinary violations involving phone use, and his use of a phone to conduct the drug transactions at issue. The court established that electronic search conditions are reasonably related to sentencing factors in two primary scenarios: (1) when the defendant instrumentalized an electronic device in the commission of the instant offense (which applied here), or (2) in rare circumstances where the defendant presents an unusually high risk of reoffending based on an extremely lengthy criminal history with specific indicators beyond mere number of prior offenses. The court emphasized that such conditions must be rigorously justified and cannot rely on generalized considerations about deterrence and public protection.
Community Service Condition: The court held the condition was procedurally and substantively reasonable. The court addressed ripeness, holding that challenges to conditions are not automatically unripe merely because they involve contingent future events; instead, courts must conduct an issue-specific analysis focusing on whether the challenge raises purely legal questions. The court found: (1) the condition was not impermissibly vague because "known and identified" bases for excusal (disability, schooling, job training) could be read into the condition; (2) the condition was not punitive because imposing conditions to incentivize employment is permissible and relates to rehabilitation; (3) the probation office's discretion to excuse employment was not an improper delegation because it was "additive" to liberty rather than subtractive; and (4) the condition was reasonably related to sentencing factors based on Jimenez's checkered work history and his own acknowledgment that unemployment correlated with criminal activity. The court also held that while the condition could potentially exceed 400 hours of community service (contrary to Sentencing Guidelines recommendations), it was justified because it incorporated a limiting principle by being contingent on unemployment and the District Court provided individualized justification.
Mental Health Treatment Condition: The court held the condition was procedurally and substantively reasonable. The District Court properly imposed the condition based on Jimenez's individual characteristics, including his expressed feelings of loneliness, grief, self-destruction, and stress that he connected to criminal activity, and his prior positive experiences with mental health services. The condition was not vague because it clearly requires participation in counseling and therapy sessions, providing adequate notice of what conduct could violate it, and the court distinguished this from the problematic condition in United States v. Carlineo. The condition did not impermissibly delegate authority because probation officers were merely authorized to handle details of treatment (such as selecting providers or scheduling), not to decide whether treatment would occur at all.
Challenge to Term of Imprisonment: The court held that Jimenez's appeal waiver in his plea agreement barred his challenge to his sentence, even though an intervening change in law (United States v. Gibson) might have lowered his Guidelines range if he were sentenced anew. The court held that while district courts may exceed the scope of limited remands for "compelling circumstances" including intervening changes in controlling law, an appeal waiver nevertheless forecloses such arguments. The court reasoned that allowing defendants to circumvent appeal waivers by raising arguments on remand that would have been barred on direct appeal would create an unwarranted exception to otherwise enforceable waivers. The fact that Jimenez waited to raise the Gibson argument until remand, rather than on his first appeal, did not change this result.