United States v. Santiago, 769 F.3d 1

In 2002 Santiago pleaded nolo contendere in Florida to lewd molestation and child abuse based on sexual conduct with a minor; he was placed on probation and required to register as a sex offender under SORNA.
He repeatedly violated probation (missed curfew, moved without permission, failed treatment, failed to register) and was imprisoned in Florida from 2005 until 2010; thereafter he moved to Puerto Rico.
In 2012 a federal indictment charged Santiago under 18 U.S.C. § 2250 for interstate travel and failure to register; he entered a plea agreement recommending a 12–18 month Guidelines range and a 12‑month sentence at the low end.
The plea agreement contained a broad waiver of appeal of “the judgment and sentence”; the magistrate discussed supervised release and explained the waiver at the change‑of‑plea colloquy, and Santiago acknowledged understanding.
At sentencing the district court imposed a 12‑month term of imprisonment and 10 years supervised release with multiple special sex‑offender conditions announced orally; the written judgment added one additional special condition (condition 13) that was not announced at sentencing.
Santiago appealed only the special sex‑offender conditions and condition 13; the government invoked the appellate‑waiver to bar review of most conditions.

Issue	Plaintiff's Argument (Santiago)	Defendant's Argument (Government)	Held
Whether Santiago can appeal special sex‑offender supervised‑release conditions despite an appeal waiver	Waiver did not specify which supervised‑release conditions would be imposed, so conditions fall outside waiver	Waiver covers the entire “judgment and sentence,” which includes supervised release and its conditions	Waiver was knowing and voluntary and bars review of the challenged special‑sex‑offender conditions (appeal dismissed as to those conditions)
Whether condition 13 (ban on sexually explicit materials/frequenting porn/sex establishments) must be vacated because it was not announced at sentencing, violating the right to be present	Condition 13 was imposed in the written judgment for the first time; Santiago had no opportunity to object and thus his right to be present was violated	Government concedes condition 13 was non‑standard but argues facts (victim’s statements, recovered porn) put Santiago on constructive notice	Court held the omission was a clear constitutional error, not harmless beyond a reasonable doubt, and vacated condition 13; remanded for re‑sentencing as to that condition

United States v. Brown, 235 F.3d 2 (1st Cir. 2000) (supervised release is an integral part of a sentence)
United States v. Mandarelli, 982 F.2d 11 (1st Cir. 1992) (supervised release is part of sentence to be served after imprisonment)
United States v. Rodríguez‑Santana, [citation="554 F. App'x 23"] (1st Cir. 2014) (appellate waiver bars review of special sex‑offender conditions under a broadly worded waiver)
United States v. Nguyen, 618 F.3d 72 (1st Cir. 2010) (district court has broad discretion to set supervised‑release conditions; waiver enforcement principles)
United States v. Teeter, 257 F.3d 14 (1st Cir. 2001) (standards for enforcing appellate waivers and miscarriage‑of‑justice exception)
United States v. Sepúlveda‑Contreras, 466 F.3d 166 (1st Cir. 2006) (defendant’s right to be present at sentencing; oral conditions control where material conflict exists)
United States v. Ortiz‑Torres, 449 F.3d 61 (1st Cir. 2006) (harmless‑error framework for unannounced written judgment conditions)