United States v. Anthony Key, 832 F.3d 837

Anthony Key pleaded guilty in 2006 to possession of child pornography, then failed to appear at sentencing and pled guilty to related perjury and failure-to-appear charges; combined prison term and lifetime supervised release were imposed.
Special Condition Number 6 of Key’s supervised release prohibited him from "possess[ing] obscene material as deemed inappropriate by the probation officer and/or treatment staff." Key did not appeal that condition at the time.
After release in 2015, halfway-house staff found sexually explicit hand-drawn pictures and stories among Key’s belongings, deemed them inappropriate, and turned them over to probation; Key was discharged from the facility for uncooperative behavior.
The probation office petitioned to revoke supervised release; the advisory guideline range for the violation was 3–9 months, but the district court varied upward and sentenced Key to 24 months’ imprisonment.
Key appealed, arguing the special condition was unconstitutionally vague and overbroad (facial and as-applied), that the materials were private noncommercial speech protected by Stanley, and that the court inadequately explained the upward variance.

Issue	Plaintiff's Argument (Key)	Defendant's Argument (Government)	Held
Whether Special Condition No. 6 is unconstitutionally vague	The term "obscene materials" and the Miller test are too subjective to give fair notice	Miller-based obscenity standard is sufficiently definite; precedent forecloses vagueness challenge	Rejected; Miller and Smith control—condition not unconstitutionally vague
Whether the condition is overbroad (facial)	A ban on "obscene material" (especially delegated to probation staff) sweeps too broadly	Condition is narrower than bans previously upheld on pornography/sexually explicit material	Rejected; ban is appropriately tailored given child-pornography conviction
Whether the condition was misapplied/as-applied to Key’s homemade drawings	Miller doesn’t apply to private, noncommercial, homemade materials; Stanley protects private possession	Condition valid for someone convicted of child-pornography offenses; court found materials were obscene	Rejected; as-applied challenge fails and court found materials obscene under the condition
Whether district court inadequately explained 24-month upward variance	Court overemphasized misconduct and didn’t address halfway-house treatment or Key’s mental/physical state	Court explained the severity of violations, repeated revocations, and lack of amenability to supervision	Rejected under plain-error review; court provided adequate explanation for variance

Miller v. California, 413 U.S. 15 (establishes obscenity test)
Smith v. United States, 431 U.S. 291 (Miller standard not unconstitutionally vague)
Stanley v. Georgia, 394 U.S. 557 (private possession of obscene material protected)
Ashcroft v. Free Speech Coal., 535 U.S. 234 (distinguishes "pornography" and "obscenity")
United States v. Ristine, 335 F.3d 692 (Eighth Circuit upholding pornographic-material bans after child-pornography convictions)
United States v. Thompson, 653 F.3d 688 (Eighth Circuit rejecting overbreadth challenges to supervised-release restrictions)
United States v. Deatherage, 682 F.3d 755 (supervised-release conditions may limit rights post-conviction)
United States v. Fonder, 719 F.3d 960 (upholding condition delegating some discretion to probation/treatment staff)
United States v. Hobbs, 710 F.3d 850 (same)
United States v. LeCompte, 800 F.3d 1209 (defendants generally cannot bring facial challenges at revocation; cited for preservation principle)
United States v. Preacely, 702 F.3d 737 (same preservation principle)
United States v. Nolan, 932 F.2d 1005 (same preservation principle)