Whether the Second Circuit Court of Appeals erred in imposing a vague communication condition of supervision that unfairly impacts the defendant's intimate familial relationships

QUESTIONS PRESENTED Whether the Second Circuit Court of Appeals erred, in violation of U.S. Const. V, when it imposed the communication condition of supervision which is vague, unfairly impacts John Doe #1’s intimate familial relationships, and is an outlier among Courts of Appeals’ decisions that have examined similar issues? Whether a federal district court is permitted boundless discretion to weigh established factors at sentencing, as the Second Circuit has held, or whether, following the majority of circuits, appellate courts must instead determine whether the district court’s weighing of sentencing factors was proper? ll