United States v. Iley, 914 F.3d 1274

Donald Iley, a Colorado accountant, admitted in a 2010 administrative "Agreement and Final Agency Order" (the Order) to professionally negligent conduct for failing to promptly remit client payroll-tax funds to the IRS; the Order imposed a $10,000 fine and five years' probation with monitoring, CPE, and quarterly compliance attestations.
Unbeknownst to the Board, Iley engaged in a continuing scheme (2009–2015) that diverted client payroll-tax payments for personal use and submitted false IRS forms; over $11 million and 140+ victims were involved.
The Board later suspended and revoked Iley’s license after learning of continuing failures to remit taxes; Iley was federally indicted and pled guilty to wire fraud and aiding in the preparation of a false tax return.
The Probation Office applied the U.S.S.G. § 2B1.1(b)(9)(C) ("Prior Order") two-level enhancement for violating a prior administrative order; the enhancement raised Iley’s Guidelines range from 78–97 months to 97–121 months.
Iley appealed, arguing (1) the Order did not expressly forbid the fraudulent conduct so the enhancement cannot apply, and (2) the Order punished negligence, not fraud, so subsequent fraud did not violate it. The Tenth Circuit affirmed.

Issue	Plaintiff's Argument (Iley)	Defendant's Argument (Gov't)	Held
Whether § 2B1.1(b)(9)(C) requires an express injunction forbidding the later criminal conduct	Order must expressly enjoin the specific fraudulent conduct to trigger enhancement	Order’s sanctions and conditions gave unmistakable notice and effectively directed Iley to stop the same conduct	Enhancement may apply even without an explicit injunction when the prior order (1) punished similar conduct, (2) imposed prospective remedial conditions reasonably calculated to curb that conduct, and (3) defendant committed the conduct while the order remained in effect (affirmed)
Whether a prior order that punished negligence cannot support enhancement when later conduct is fraudulent	Negligence differs from fraud; a warning against negligence does not equate to a prohibition on stealing	Punishing negligent conduct that is the same or similar in substance still notifies and bars the conduct; later intentional fraud shows aggravated intent deserving enhancement	No mental-state symmetry required; later fraudulent repetition of the same or similar conduct violates the order and supports the enhancement (affirmed)

United States v. Pentrack, 428 F.3d 986 (10th Cir. 2005) (consent order that targeted deception provided adequate notice to support Prior Order enhancement)
United States v. Nash, 729 F.3d 400 (5th Cir. 2013) (fine and warning letter sufficiently directed defendant to stop such conduct; enhancement appropriate)
United States v. Jokhoo, 806 F.3d 1137 (8th Cir. 2015) (administrative sanctions and penalties that followed a hearing supported application of the enhancement)
United States v. Goldberg, 538 F.3d 280 (3d Cir. 2008) (distinguishes informal warnings from definite administrative results like consent decrees; enhancement requires a specific directive)
United States v. Wallace, 355 F.3d 1095 (7th Cir. 2004) (informal warning/voluntary discontinuance insufficient to trigger enhancement)