United States v. Qubid Coleman, 806 F.3d 941

Coleman delivered crack for a drug conspiracy; indicted and faced a mandatory life sentence due to prior drug convictions.
After competency proceedings (one examiner found malingering), Coleman pleaded guilty pursuant to a written plea agreement that included appellate and collateral-attack waivers and an admission of at least 280 grams of crack.
At the change-of-plea hearing Coleman said he understood the agreement and that counsel had read it to him; the court addressed the appellate waiver but did not personally explain the collateral-attack (§ 2255) waiver as required by Rule 11.
At sentencing the court granted the government’s § 5K1.1 substantial-assistance motion and imposed 324 months’ imprisonment plus a 10-year term of supervised release with unspecified “standard conditions.”
Coleman did not object below; on appeal he challenged (1) the Rule 11 omission regarding the collateral-attack waiver and (2) vagueness and procedural defects in the supervised-release conditions.

Issue	Coleman’s Argument	Government’s Argument	Held
Rule 11: failure to personally advise defendant of collateral-attack waiver	The omission violated Rule 11 and affected substantial rights, so plea should be vacated	Written plea agreement and colloquy about understanding suffice; any error was harmless	Affirmed conviction: omission was plain error but did not affect substantial rights (no reasonable probability Coleman would go to trial)
Scope of collateral-attack waiver (ineffective-assistance claims)	Waiver could bar collateral attack; challenges to counsel remain possible	Conceded contractual language was too narrow and agreed not to enforce waiver against ineffective-assistance claims	Government’s concession remedied the drafting defect; waiver will not be enforced to bar ineffective-assistance claims concerning the plea
Supervised-release conditions: vagueness and procedural adequacy	Conditions were vague and court failed to explain § 3553(a)-based reasons; remand requested	Government conceded error and waived reliance on appellate waiver to avoid remand	Sentence vacated and case remanded for full resentencing to reassess imprisonment and supervised release conditions

United States v. Kappes, 782 F.3d 828 (7th Cir. 2015) (procedural and substantive rules for imposing supervised-release conditions)
Hurlow v. United States, 726 F.3d 958 (7th Cir. 2013) (collateral-attack waivers cannot bar ineffective-assistance claims attacking the plea)
United States v. Downs, 784 F.3d 1180 (7th Cir. 2015) (when one component of sentence is altered on appeal, whole sentence may need reassessment)
United States v. Williams, 559 F.3d 607 (7th Cir. 2009) (defendant bears burden to show Rule 11 error affected substantial rights)
United States v. Thompson, 777 F.3d 368 (7th Cir. 2015) (example of impermissibly vague supervised-release conditions)
United States v. Polak, 573 F.3d 428 (7th Cir. 2009) (plain-error review for unpreserved Rule 11 errors)
United States v. Sura, 511 F.3d 654 (7th Cir. 2007) (record can supply adequate substitute for omitted Rule 11 colloquy)
Dominguez Benitez v. United States, 542 U.S. 74 (2004) (standard for showing Rule 11 plain error affected substantial rights)
United States v. Vonn, 535 U.S. 55 (2002) (scope of Rule 11 and plain-error review)