Of the Federal Circuit, sitting by designation. *

United States Court of Appeals

For the First Circuit

No. 04-1409

UNITED STATES OF AMERICA,

Appellee,

v.

LUIS SEPÚLVEDA-CONTRERAS,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. Salvador E. Casellas, U.S. District Judge]

Before

Boudin, Chief Judge,

Torruella and Dyk, Circuit Judges. *

Anita Hill-Adames, on brief for appellant.

Mariana E. Bauzá-Almonte, Assistant United States Attorney,

H.S. García, United States Attorney, and Nelson Pérez-Sosa,

Assistant United States Attorney, Senior Appellate Attorney, on

brief for appellee.

October 25, 2006
 Torres-Colón is not a party to this appeal. 1

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TORRUELLA, Circuit Judge. On September 17, 2003,

Defendant-Appellant Luis Sepúlveda-Contreras ("Sepúlveda") pled

guilty to a charge of carjacking under 18 U.S.C. §§ 2 and 2119(2).

Sepúlveda was later sentenced to 235 months in prison and five

years of supervised release. He now appeals, arguing that: (1) the

district court violated his right to be present at sentencing by

imposing certain conditions of supervised release for the first

time in the written judgment without announcing them orally at

sentencing; and (2) the district court improperly delegated to the

probation officer the responsibility for determining the number of

drug tests he must undergo while on supervised release. After

careful review, we vacate the aforementioned supervised release

conditions and remand for re-sentencing consistent with this

opinion.

I. Background

On September 23, 2002, Sepúlveda and his co-defendant,

Frankie Torres-Colón, were walking, accompanied by a small child, 1

in Río Piedras, Puerto Rico, when they saw a man driving a blue

Dodge Intrepid pull into a school parking lot. The two defendants

approached the driver after he exited his car, threatened him with

knives, and demanded his car keys. The victim initially complied,

but when the defendants insisted that he get into the car with
 Sepúlveda's Presentence Report ("PSR") identified him as a 2

career offender and set his Base Offense Level at 34. It then gave

him a three-level deduction for acceptance of responsibility,

resulting in a Total Offense Level at 31. Combined with a Criminal

History Category of VI due to his career offender status, the

applicable Guideline range was 188-235 months in prison.

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them, he refused and a struggle ensued, during which one or both

defendants stabbed him. The defendants then stole the car.

On February 13, 2004, the district court sentenced

Sepúlveda to 235 months in prison -- which represented the upper

limit of the applicable Guideline range -- and a five-year term of

supervised release. The court based its decision to sentence 2

Sepúlveda to the upper limit of the applicable range on several

factors, including: (1) that Sepúlveda had "been previously

involved and convicted of criminal charges at the state level which

clearly shows that [he] has no respect for the criminal justice

system"; (2) that Sepúlveda, who was given an electronic monitoring

bracelet as part of supervised release from state prison on an

unrelated conviction, was wearing the bracelet when he committed

the carjacking; (3) that the carjacking resulted in permanent and

life threatening bodily injury and also put a minor at risk; and

(4) the court's belief that "imposing a stiff sentence will be a

step towards returning control of the communit[y] to its

residents." The court also stated that "[t]he terms and conditions

[of the supervised release] shall be set forth in the [written]

judgment." The court decided not to impose a fine -- although it
 We will refer to these conditions as the "financial disclosure 3

condition" and the "search condition."

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could have imposed a fine ranging from $17,500 to $175,000 -- due

to Sepúlveda's financial condition.

The written judgment was entered on February 17, 2004.

The judgment contained thirteen conditions denominated as

"standard" by the Guidelines and several conditions denominated as

"mandatory" by the Guidelines. See U.S.S.G. § 5D1.3. The judgment

also included three conditions that are the subject of this appeal.

First, the judgment stated that "[t]he defendant shall submit to

one drug test within 15 days of release from imprisonment and at

least two periodic drug tests thereafter as required by the

Probation Officer." (emphasis added). The judgment included two

additional conditions:

1. The defendant shall provide the U.S.

Probation Officer access to any financial

information upon request, and shall produce

evidence to the U.S. Probation office to the

effect that income tax returns have been duly

filed with the Commonwealth of Puerto Rico

Department of Treasury as required by law.

2. The defendant shall submit his person,

residence, office or vehicle to a search,

conducted by a United States Probation Officer

at a reasonable time and in a reasonable

manner, based upon reasonable suspicion of

contraband or evidence of a violation of a

condition of release; failure to submit to a

search may be grounds for revocation; the

defendant shall warn any other residents that

the premises may be subject to searches

pursuant to this condition.3
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After filing this appeal, on February 18, 2004,

Sepúlveda's counsel filed a brief pursuant to Anders v. California,

386 U.S. 738 (1967), requesting to withdraw. We rejected this

request and ordered counsel to file a merits brief addressing: (1)

whether the district court violated Sepúlveda's right to be present

at sentencing by imposing the two non-mandatory, non-standard

conditions in the written judgment without first announcing them at

oral argument; and (2) whether the district court improperly

delegated to the probation officer the responsibility for

determining the number of drug tests Sepúlveda must undergo while

on supervised release.

II. Discussion

A. Non-Mandatory, Non-Standard Conditions

Sepúlveda first argues that the district court violated

his right to be present at sentencing by imposing the financial

disclosure and search condition for the first time in the written

judgment without orally announcing them at sentencing.

We begin by noting that "[d]efendants have a right,

guaranteed by the United States Constitution and the Federal Rules

of Criminal Procedure, to be present during sentencing." MeléndezSantana v. United States, 353 F.3d 93, 99 (1st Cir. 2003),

overruled, in part, on other grounds by United States v. Padilla,

415 F.3d 211, 215 (1st Cir. 2005). Accordingly, "where the

conditions of supervised release announced at the sentencing
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hearing conflict in a material way with the conditions of

supervised release in the written sentencing order, the oral

conditions control." Id. at 100. In Meléndez-Santana, we found

that a district court's imposition of a drug treatment condition

for the first time in the written judgment violated the defendant's

right to be present because it "imposed a potentially significant

new burden on the Defendant." Id.

However, we have stated that "no material conflict exists

where the defendant is on notice that he is subject to the terms

included in the written judgment." United States v. Ortiz-Torres,

449 F.3d 61, 74 (1st Cir. 2006). In determining whether Sepúlveda

had notice of the two conditions imposed in the written judgment,

we must first consider the type of condition. The Sentencing

Guidelines specify different categories of conditions for

supervised release: (1) "mandatory" conditions, U.S.S.G. § 5D1.3

(a); (2) "standard" conditions, id. § 5D1.3(c); (3) "special"

conditions, which become "recommended" if certain criteria are met

and "may otherwise be appropriate in particular cases," id. § 5D1.3

(d); (4) "special" conditions that "may be appropriate on a caseby-case basis, id. § 5D1.3(e); and (5) other conditions that meet

certain criteria, id. § 5D1.3(b). Defendants are deemed to be on

constructive notice for mandatory and standard conditions announced

for the first time in a written judgment, and therefore have no

right-to-be-present claim with respect to any such condition. See
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United States v. Vega-Ortiz, 425 F.3d 20, 22-23 (1st Cir. 2005)

(mandatory conditions); United States v. Tulloch, 380 F.3d 8, 13-14

& n.8 (1st Cir. 2004) (per curiam) (standard conditions).

We also note that at least two other circuits have held

that defendants have constructive notice for "special" conditions

that become "recommended" when certain criteria are met. See,

e.g., United States v. Torres-Aguilar, 352 F.3d 934, 937 (5th Cir.

2003); United States v. Asunción-Pimental, 290 F.3d 91, 94 (2d Cir.

2002) (stating that, where specific factors necessary to make

"special" conditions "recommended" are present, "these 'special'

conditions are no different in practical terms from 'standard'

conditions, that is, they are generally recommended"). But see

United States v. Thomas, 299 F.3d 150, 155 (2d Cir. 2002) (holding

that conditions announced for the first time in a written judgment

that "govern more than the basic administration" of supervised

release violate a defendant's right to be present at sentencing).

The financial disclosure condition imposed by the

district court is a "special" condition that becomes "recommended"

if "the court imposes an order of restitution, forfeiture, or

notice to victims, or orders the defendant to pay a fine."

U.S.S.G. § 5D1.3(d)(3). However, although the district court could

have imposed a fine or restitution order on Sepúlveda, it chose not

to. Therefore, the condition did not become a "recommended"

condition. The search condition is not specifically enumerated in
 The government argues that Sepúlveda has waived any argument 4

regarding the search condition because he "mentioned", but did not

"discuss[]" the condition. We disagree. While Sepúlveda focuses

much of his argument on the financial disclosure condition, he

mentions the search condition and his brief clearly challenges it.

This is not a situation where we are forced to piece together

Sepúlveda's argument for him, see United States v. Zannino, 895

F.2d 1, 17 (1st Cir. 1990), and we therefore find no waiver.

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any of the conditions listed in § 5D1.3; instead, it falls under

the "catch-all" provision found in § 5D1.3(b), and is therefore not

a "recommended" condition. In sum, both of the conditions imposed

by the district court are non-mandatory, non-standard, and nonrecommended conditions of supervised release.

To our knowledge, no circuit has upheld the imposition of

such conditions for the first time in a written judgment in the

face of a right-to-be-present claim. We decline to do so here.

From our review of the record, there is nothing that would have

served to put Sepúlveda on constructive notice that the two

conditions would be imposed for the first time in the written

judgment. Furthermore, the imposition of both conditions could

potentially impose a significant burden on Sepúlveda. We therefore

find that the district court erred in imposing these two conditions

for the first time in the written judgment.4

Having concluded that the district court committed error,

we must now address whether we review for harmless or plain error.

Sepúlveda argues that he did not have an opportunity to object to

the conditions at sentencing, and that our review is therefore for
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harmless error. The government argues that Sepúlveda forfeited his

right to object and that our review is thus for plain error. We

agree with Sepúlveda.

Right-to-be-present claims are subject to harmless error

analysis if the defendant had no opportunity to object before the

conditions were imposed. See Ortiz-Torres, 449 F.3d at 74 (citing

Meléndez-Santana, 353 F.3d at 108). Here, since the conditions

were announced for the first time in the written judgment,

Sepúlveda had no opportunity to object to their imposition.

The government makes two arguments for plain error.

First, it notes that the district court stated at sentencing that

"the terms and conditions [of supervised release] shall be set

forth in the judgment." According to the government, Sepúlveda

should have objected to having the terms and conditions set forth

in the written judgment. We disagree. As our discussion above

illustrates, because these were special, non-mandatory and nonrecommended conditions, Sepúlveda did not have constructive notice

that they would be imposed in the written judgment. We see no

reason for holding that Sepúlveda forfeited objections to

conditions he had no reason to anticipate.

Second, the government argues that Sepúlveda forfeited

the argument by not filing any objections once the written judgment

was entered. We note that it is theoretically possible for a

defendant to object to a previously unannounced written condition
 While Gallant presented a different factual scenario than the 5

instant case, the policy concerns expressed in that opinion apply

with full force to this case.

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after judgment is entered. See, e.g., Fed. R. Crim. P. 35(a)

("Within 7 days after sentencing, the court may correct a sentence

that resulted from arithmetical, technical, or other clear

error."). However, given the context of this case, there are

several reasons why we are not inclined to find that Sepúlveda

should have objected after judgment was entered.

First, we have stated that, in the sentencing context, "a

post-sentence objection is not necessarily required to preserve the

issue for appeal if the defendant could not reasonably have

anticipated the issue would arise until after the court ruled."

United States v. Cortés-Claudio, 312 F.3d 17, 24 (1st Cir. 2002)

(citing United States v. Gallant, 306 F.3d 1181, 1188-89 (1st Cir.

2002)). As we have already discussed, Sepúlveda could not have

reasonably anticipated the imposition of these conditions. Second,

we have also noted that "[t]here is . . . a need for finality and

few trial judges would warm to a rule which requires continued

argument after the court gives its sentence." Gallant, 306 F.3d at

1188-89. Finally, "unlike other areas, there is no Federal Rule 5

of Criminal Procedure giving advance notice to counsel of a

requirement to make post-sentence objections." Id. at 1189. It

would be unwise to encourage a practice of entering objections

after the written judgment has entered, for doing so would
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undermine the interest in finality. For these reasons, we reject

the government's argument that Sepúlveda forfeited the argument by

not objecting after the written judgment was entered. We will

therefore review the imposition of the two conditions for harmless

error.

Under the harmless error standard of review, the burden

is on the government to prove that the error in question is

harmless. United States v. Vázquez-Rivera, 407 F.3d 476, 489 (1st

Cir. 2005). "The standard of proof, however, depends on whether

the error is conceived of as constitutional." Id. If the error is

constitutional in nature, "the government has the burden of proving

beyond a reasonable doubt that the error did not affect the

defendant's substantial rights." Id. If the error is not

constitutional in nature, "the government has the burden of

demonstrating the absence of any grave doubt" regarding the

harmlessness of the error. See id.

Here, the government has the burden of proving beyond a

reasonable doubt that the violation of Sepúlveda's constitutional

right to be present at his sentencing did not compromise his

ability to object to the sentencing conditions imposed by the

district court. To meet this burden, the government would need to

show, beyond a reasonable doubt, that the special conditions would

have been imposed even if Sepúlveda had been present. It has
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failed to do so. We therefore vacate the financial disclosure and

search conditions in Sepúlveda's sentence.

B. Improper Delegation

The written judgment stated that Sepúlveda "shall submit

to one drug test within 15 days of release from imprisonment and at

least two periodic tests thereafter as required by the Probation

Officer." (emphasis added). Both Sepúlveda and the government

acknowledge that, under our precedent, the district court

improperly delegated to the probation officer the authority to

determine the number of drug tests Sepúlveda must undergo while on

supervised release. However, both parties erroneously assume that

our review is for plain error, and that the improper delegation

cannot meet this rigorous test.

In Meléndez-Santana, 353 F.3d at 106, we held that the

plain language of 18 U.S.C. § 3583(d) "requires courts to determine

the maximum number of drug tests to be performed beyond the

statutory minimum of three." Delegating this authority to another

entity is improper. We also held that the improper delegation

constituted plain error. Recently, in Padilla, 415 F.3d at 215, we

overruled Meléndez-Santana's holding that such improper delegation

constituted plain error, although we declined to reconsider

Meléndez-Santana's holding that the delegation was error. If we

were reviewing for plain error, it is unlikely that Sepúlveda would

be successful.
 Furthermore, the constructive notice rationale that we have 6

applied in other cases, see Tulloch, 380 F.3d at 13, is

inapplicable here. Although drug testing is a mandatory condition

under the Guidelines, the Guidelines specifically state that the

number of drug tests are determined by the court, not the probation

officer. See U.S.S.G. § 5D1.3(a)(4). Therefore, even if Sepúlveda

were on constructive notice of the drug testing condition, he

cannot be held to have had constructive notice that the district

court would delegate to the probation officer the authority to

determine the number of drug tests he must undergo.

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However, Sepúlveda's case is distinguishable from Padilla

and Meléndez-Santana because Sepúlveda never had an opportunity to

object to the wording of the drug testing condition. In both 6

Meléndez-Santana and Padilla, the district court included the drug

testing condition that contained the improper delegation in both

the oral and written judgments. By contrast, in the instant case,

the district court announced the drug testing condition only in the

written judgment.

We have stated that "'typically, the court of a appeals

reviews a district court's imposition of a special condition of

. . . supervised release' unless 'the sentencing court affords the

defendant an opportunity to object to the condition but the

defendant holds his tongue,' in which case review is for plain

error." United States v. Mojica-Rivera, 435 F.3d 28, 35 (1st Cir.

2006) (quoting United States v. Brown, 235 F.3d 2, 3 (1st Cir.

2000)). In Mojica-Rivera, the district court included a drug

testing condition in the written judgment that it did not include

in the oral pronouncement of the sentence. In that case, we
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reviewed the imposition of the drug testing condition for abuse of

discretion, see id., and we follow the same course today. Given

our determinations in Meléndez-Santana and Padilla that similar

language in a district court's judgment constituted "clear and

obvious error," see Padilla, 415 F.3d at 220, we herein conclude

that the district court in this case abused its discretion by

delegating to the probation officer the authority to determine the

number of drug tests Sepúlveda must undergo while on supervised

release. We vacate the drug testing provision in Sepúlveda's

sentence.

III. Conclusion

For the forgoing reasons, we vacate the supervised

release conditions regarding financial disclosure, searches, and

drug testing; and we remand for re-sentencing consistent with this

opinion.

Vacated and Remanded.