Henderson v. United States, 133 S. Ct. 1121

Henderson pleaded guilty in 2010 to felon in possession of a firearm and was sentenced to an above-Guidelines term of 60 months by the district court.
The district court imposed the longer sentence in part to qualify Henderson for an in-prison rehabilitative program, a goal Henderson’s counsel did not object to at sentencing.
After sentencing but before appeal, Tapia v. United States held that imposing or lengthening a sentence to promote rehabilitation is unlawful, rendering Henderson’s sentence unlawful.
The Fifth Circuit denied relief under Rule 52(b) because the error was not plain at the time of the district court’s ruling, owing to unsettled circuit law.
The Supreme Court granted certiorari to resolve differences among Circuits about whether plainness under Rule 52(b) should be assessed at trial or appellate review.
The Court ultimately held that plain error must be assessed at the time of appellate consideration, reversing the Fifth Circuit and remanding.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Timing of plain error under Rule 52(b)	Henderson (plaintiff) argued plainness is evaluated at review.	Respondent argued plainness should be determined at trial when error occurred.	Plainness assessed at time of appellate consideration.
Effect of unsettled law at trial	Unsettled law support treating later clarity as plain at review.	Unsettled law should not make trial errors plainly discoverable on appeal.	Unsettled law can be plain at review; time-of-review approach favored.
Johnson v. United States relevance	Johnson supports plainness being enough at appeal when law later becomes settled.	Johnson should not govern mid-unsettled-law cases as here.	Johnson applied to support time-of-appeal plainness in this context.
Policy goals of contemporaneous objection versus Rule 52(b)	Plain-error rule serves to protect fairness when new law is applied on appeal.	Preservation and contemporaneous objection remain important to efficiency.	Rule 52(b) relief can accommodate post-trial law changes without undermining preservation.
Practical consequences of the rule	Time-of-appeal plainness reduces injustice when the law becomes clearly favorable on appeal.	Time-of-appeal approach risks floodgates and complexity.	Time-of-appeal interpretation better aligns with final-law-rule application.

United States v. Olano, 507 U.S. 725 (1993) (establishes four Olano prongs for Rule 52(b) plain-error review)
Tapia v. United States, 564 U.S. 319 (2011) (prohibits using prison terms to promote rehabilitation)
Johnson v. United States, 520 U.S. 461 (1997) (plainness at time of appellate consideration when law later clears)
Schooner Peggy, 1 U.S. Cranch 103 (1801) (principle that appellate law must be applied as of decision time)
Thorpe v. Housing Authority of Durham, 393 U.S. 268 (1969) (applies law in effect at time of decision)
United States v. Frady, 456 U.S. 152 (1982) (timeliness and plain-error considerations in relief analysis)
United States v. Atkinson, 297 U.S. 157 (1936) (structural basis for review with fairness considerations)
Cordery, 656 F.3d 1103 (10th Cir. 2011) (time of review vs time of error in plain-error analysis (cited for contrast))
Mouling, 557 F.3d 658 (D.C. Cir. 2009) (discusses timing in plain-error context)
Garcia, 587 F.3d 509 (2d Cir. 2009) (plain-error considerations in unsettled-law scenarios)
Ross, 77 F.3d 1525 (7th Cir. 1996) (plain-error framework discussions)
Escalante-Reyes, 689 F.3d 415 (5th Cir. 2012) (concerned with plain-error standards and rule implications)