United States v. Boudreau, 58 F.4th 26

Defendant Jason D. Boudreau had prior sexual/offense history: 2009 conviction (sexualized simple assault of an 11‑year‑old), 2012 second‑degree child molestation, and 2014 state child‑pornography possession conviction.
In 2015 uploads and device seizures, law enforcement found hundreds of child‑pornography images tied to Boudreau; federal indictment charged 34 counts; he pleaded guilty to Counts 19 and 34 under a plea agreement that dismissed the other counts.
The plea agreement included an express appeal waiver: defendant waived appeals of conviction and sentence if the sentence was within or below the Guidelines range determined by the court.
The PSR and district court applied several stipulated and additional Guidelines enhancements (including pattern‑of‑activity), producing offense level 33, Criminal History Category IV, Guidelines range 188–235 months; the court sentenced Boudreau to 235 months and lifetime supervised release.
Special supervised‑release conditions included a suspicionless search provision, restrictions on internet‑capable devices, and a prohibition on contact with persons under 18.
Boudreau appealed, arguing the appeal waiver was invalid (Rule 11 colloquy failures), challenging Guidelines calculations and supervised‑release conditions; the First Circuit held the waiver valid and enforceable and dismissed the appeal.

Issue	Plaintiff's Argument (Boudreau)	Defendant's Argument (Government)	Held
Validity/enforceability of appeal waiver	Waiver invalid because plea colloquy and agreement flaws meant he did not "freely and intelligently" waive appeals	Waiver is clear, defendant confirmed understanding under oath, counsel represented him, waiver enforceable	Waiver valid and bars appeal; appeal dismissed
Adequacy of Rule 11 colloquy	District court failed to advise right to withdraw plea and failed to explain nature of each charge, undermining waiver	These Rule 11 errors (if any) did not affect his ability to understand waiver; arguments were underdeveloped or waived	Colloquy sufficient for waiver; asserted Rule 11 defects do not defeat waiver and fail under plain‑error review
Supervised‑release special conditions	Conditions (suspicionless searches, device/internet ban, no contact with minors) are overbroad and amount to a miscarriage of justice	Conditions are reasonably related to sentencing goals and supported by precedent; within plea scope	Conditions upheld; no clear or obvious error and not a miscarriage of justice
Challenge to overall validity of plea agreement	Plea agreement procedurally invalid (Rule 11 errors) so waiver and agreement should be vacated	Record shows plea was knowing and voluntary; plain‑error standard applies and defendant cannot show but‑for effect	Challenge meritless under plain‑error review; no reasonable probability he would have rejected the plea

United States v. Teeter, 257 F.3d 14 (1st Cir. 2001) (establishes three‑factor test for validity of appeal waivers)
United States v. Morillo, 910 F.3d 1 (1st Cir. 2018) (applies Teeter; clarifies standards for plea‑waiver clarity and colloquy)
United States v. Morales‑Arroyo, 854 F.3d 118 (1st Cir. 2017) (dismissal of appeal when valid waiver applies)
United States v. Rivera‑López, 736 F.3d 633 (1st Cir. 2015) (miscarriage‑of‑justice standard for piercing appeal waivers and review of supervised‑release conditions)
United States v. Dominguez‑Benitez, 542 U.S. 74 (2004) (plain‑error standard for Rule 11 errors affecting pleas)
United States v. Windle, 35 F.4th 62 (1st Cir. 2022) (upholding suspicionless search condition as reasonably related to supervised‑release goals)