22-1013
United States of America v. Rosado

                                         In the
                  United States Court of Appeals
                             For the Second Circuit

                                     August Term 2023

                                      No. 22-1013-cr

                           UNITED STATES OF AMERICA,

                                                          Appellee,

                                     STEVE ROSADO,

                                                          Defendant-Appellant,




                   Appeal from the United States District Court
                      for the Southern District of New York
          No. 1:21CR00003 (JSR), Jed S. Rakoff, District Judge, Presiding.
                (Argued December 15, 2023; Decided July 30, 2024)



       Before:       PARKER, NATHAN, and MERRIAM Circuit Judges.

       Defendant-Appellant Steve Rosado appeals from a judgment of the United
States District Court for the Southern District of New York (Rakoff, J.). He
challenges seven additions to his conditions of supervised release on the ground
that they were not orally pronounced at sentencing, but were added only later in
the written judgment of conviction. We agree with Rosado that the oral
pronouncement of his sentence does not match his subsequent written judgment.
The oral pronouncement controls, and so any burdensome punishments or
restrictions added in the written judgment should be removed. See United States
v. Rosario, 

 (2d Cir. 2004). Accordingly, we VACATE and
REMAND to the district court to strike the challenged conditions from the
written judgment. In a concurrently issued summary order, we affirm the
district court’s judgment as to other challenges raised pro se by Rosado.

                   MATTHEW B. LARSEN, Assistant Federal Defenders, Appeals
                   Bureau, Federal Defenders of New York, New York, NY for
                   Defendant-Appellant

                   JANE Y. CHONG, Assistant United States Attorney (Jonathan L.
                   Bodansky and Stephen J. Ritchin, Assistant United States
                   Attorneys, on the brief), for Damian Williams, United States
                   Attorney for the Southern District of New York, New York,
                   NY

PER CURIAM:

      In November 2021, Steve Rosado pled guilty to attempted enticement of a

minor to engage in illegal sexual activity in violation of 

(b) and

attempted receipt of child pornography after having been convicted of sex

offenses involving minors in violation of 18 U.S.C § 2252A. On appeal, he

challenges seven additions to his conditions of supervised release on the ground

that the district court failed adequately to pronounce them at sentencing but later

added them to the written judgment of conviction.

      We agree that those additions should have been pronounced at sentencing

as required by Federal Rule of Criminal Procedure 43(a) and our precedent. See,

e.g., United States v. Washington, 

 (2d Cir. 2018). Accordingly, we


                                         2
VACATE and REMAND to the district court to enter a modified judgment of

conviction removing the seven unpronounced additions. 1

                                 BACKGROUND

      In December 2020, Rosado met with a woman whom he believed to be the

mother of two girls, ages 12 and 9. In previous online exchanges with the

woman, who was, unbeknownst to him, actually an undercover law enforcement

agent, Rosado expressed a desire to engage in sexual conduct with the daughters.

As Rosado and the undercover agent headed to her purported apartment, he was

arrested. At the time of his arrest, Rosado was a registered sex offender and had

two prior convictions for sex offenses involving minors.

      Rosado was subsequently charged with (1) attempted enticement of a

minor to engage in illegal sexual activity, in violation of 

(b)

(“Count One”), (2) committing that offense while being required by law to

register as a sex offender, in violation of 18 U.S.C. § 2260A (“Count Two”), and

(3) attempted receipt of child pornography after having been convicted of sex




1Proceeding pro se, Rosado raised several other challenges to his convictions that
we have rejected in a summary order filed this day.
                                          3
offenses involving minors, in violation of 18 U.S.C § 2252A(a)(2)(B) and (b)(1)

(“Count Three”).

      Rosado entered into an agreement to plead guilty to Counts One and

Three. The district court sentenced Rosado to 240 months’ imprisonment, to be

served concurrently on both counts, followed by a lifetime term of supervised

release. In addition to imposing most of the mandatory and “standard”

conditions of supervised release detailed in United States Sentencing Guidelines

(“U.S.S.G.”) § 5D1.3(a) and (c), the district court announced several other

conditions that were specific to Rosado. Of these, Conditions Three, Four, and

Six are relevant to this appeal. At sentencing, the district court articulated those

conditions as follows:

      Condition Three: Rosado “will not have any deliberate contact with any
      child under 18 years of age unless approved by the probation office[.]”

      Condition Four: Rosado “will permit the U.S. Probation Office to install
      any application or software that allows it to survey and/or monitor his
      computer and similar activity[.]”

      Condition Six: Rosado “will undergo a sex offense specific evaluation and
      participate in an outpatient sex offender treatment and/or outpatient
      mental health treatment program on the standard terms and conditions[.]”

App’x at 32-33. However, in its subsequent written judgment, the district court

added multiple requirements to Conditions Three, Four, and Six that had not

                                          4
been pronounced at sentencing. In his appeal, Rosado challenges the following

seven additions:

Condition 3:

   • “You must not loiter within 100 feet of places regularly frequented by
     children under the age of 18, such as schoolyards, playgrounds, and
     arcades.”

   • “You must not view and/or access any web profile of users under the age
     of 18. This includes, but is not limited to, social networking websites,
     community portals, chat rooms or other online environment
     (audio/visual/messaging), etc. which allows for real time interaction with
     other users, without prior approval from your probation officer.”

Condition 4:

   • “[Y]ou must allow the probation officer to conduct initial and periodic
     unannounced examinations of any Device(s) that are subject to
     monitoring.”

   • “You will not utilize any peer-to-peer and/or file sharing applications
     without the prior approval of your probation officer.”

Condition 6:

   • You must “submi[t] to polygraph testing[.]”

   • You must “refrain[] from accessing websites, chatrooms, instant
     messaging, or social networking sites to the extent that the sex offender
     treatment and/or mental health treatment program determines that such
     access would be detrimental to your ongoing treatment.”




                                        5
   • “You will not view, access, possess, and/or download any pornography
     involving adults unless approved by the sex-offender specific treatment
     provider.”

App’x at 40.

                             STANDARD OF REVIEW

        “[W]hether the spoken and written terms of a defendant’s sentence differ

impermissibly” presents a question of law that we review de novo. Washington,

. We generally review an issue of law for plain error where, as

here, the defendant has failed to raise the issue in the district court. “But when

the point of law on appeal is a term of the defendant’s sentence and the

defendant lacked prior notice in the district court that the term would be

imposed, we will review the issue de novo even if the defendant failed to raise an

objection in the district court.” 

                                    DISCUSSION

   I.      The Unpronounced Additions to Conditions Three, Four, and Six

        Federal Rule of Criminal Procedure 43(a)(3) requires that a defendant be

present at sentencing. See United States v. Sims, 

 (2d Cir. 2024).

We have interpreted that rule to require that the sentencing court orally

pronounce special conditions of supervised release in open court. 

 We have



                                          6
been clear “that in the event of variation between an oral pronouncement of

sentence and a subsequent written judgment, the oral pronouncement controls,

and any burdensome punishments or restrictions added in the written judgment

must be removed.” United States v. Rosario, 

 (2d Cir. 2004)

(citations omitted); see also Sims, 

 (“[W]hen there is a conflict

between the court’s unambiguous oral pronouncement of a special condition and

the written judgment, the oral pronouncement controls.”).

      Our review of the record yields no indication that the district court

pronounced at sentencing or otherwise provided adequate notice that the seven

additional requirements would be imposed. The government contends that the

additions were included in the Presentence Report (“PSR”) and that the district

court, accordingly, had adopted the PSR’s proposed conditions into its sentence.

According to the government, the district court “paraphrased the first sentences

of these special conditions as they had been described” in the PSR. Appellee’s

Br. 30. But that is not sufficient. If it were, a defendant would leave his

sentencing without the requisite certainty as to which portions of the PSR’s

proposed conditions were imposed and would be left guessing until he obtained




                                           7
a copy of the subsequent written judgment. 2 That lack of clarity is exactly what

Rule 43(a)(3) is intended to guard against. Sentencing must occur in open court

in the defendant’s presence. This requirement affords a defendant and his

counsel an opportunity to obtain a clear understanding of the terms of the

sentence and to object to or seek clarification of its components.

      Although we have identified certain circumstances in which conditions of

supervised release need not be orally pronounced, no such circumstances are

present here. For example, when challenged modifications in the written

judgment add “mere ‘basic administrative requirements that are necessary to

supervised release,’” we do not require pronouncement at sentencing.

Washington, 

 (quoting Rosario, 

). We have also

allowed for additions in the written judgment that merely “clarify the terms of

the spoken sentence.” 

 But we do not make such allowances where, as here,

the modifications or additions impose new “burdensome punishments or


2We have previously suggested that a district court may orally pronounce
supervised release conditions by “indicat[ing] that it [will] incorporate the
conditions listed in the PSR.” United States v. Thomas, 

 (2d Cir.
2002). But without delving into what specifically qualifies as sufficient for
making a district court’s intention to adopt the conditions recommended in the
PSR clear to a defendant, we do not believe that the district court clearly
indicated its intention to do so here.


                                         8
restrictions,” Rosario, 

, or where there is “a substantive

discrepancy between the spoken and written versions of” the sentence,

Washington, 

. As we explain, the seven additions at issue here

should not have been imposed without having been orally pronounced.

      For starters, the two written additions to Condition Three significantly

restrict Rosado’s movement and activity well beyond the pronounced condition’s

instruction that he is not permitted to have any deliberate contact with children

without the permission of the Probation Office. These additions are neither

clarifications nor necessary basic administrative requirements. Rather, they

impose significant new restrictions on Rosado’s liberty.

      As to Condition Four, one challenged addition in the written judgment

provides that Rosado shall “not utilize any peer-to-peer and/or file sharing

applications without the prior approval of [his] probation officer.” App’x at 40.

The other requires Rosado to “allow the probation officer to conduct initial and

periodic unannounced examinations of any Device(s) that are subject to

monitoring.” 

 These additions are not necessary administrative requirements

for monitoring Rosado’s computer activity. They are substantive add-ons that




                                          9
do significantly more than clarify the version of Condition Four that was

pronounced at sentencing.

      As to Condition Six, the district court pronounced at sentencing that

Rosado must “undergo a sex offense specific evaluation and participate in an

outpatient sex offender treatment and/or outpatient mental health treatment

program on the standard terms and conditions.” App’x at 33. The government

contends that the district court’s statement at sentencing that Rosado must

undergo treatment under the “standard terms and conditions” made clear that

all of the requirements recommended in the PSR would be included in the

written judgment. We are not persuaded. A reference to “standard terms and

conditions”—even to the “standard terms and conditions” of a sex offender

treatment program—would not notify a defendant and his counsel of the

significant additional restrictions that subsequently appeared in Rosado’s written

judgment. For instance, such a reference would fail to apprise him that he would

not be able to view legal adult pornography or access “websites” or “social

networking sites”—which, by these broad terms, would include Google,

LinkedIn, or WSJ.com—that his program found detrimental to his treatment.

App’x at 40.



                                       10
      Moreover, a reference to “standard terms and conditions” does not make

clear to a defendant that he would be required to undergo polygraph testing. In

fact, this Court has already held that merely pronouncing that a defendant must

participate in a sex offender treatment program does not obviate the need to

specifically pronounce at sentencing that such treatment will include polygraph

testing. See Washington, 

 (noting that polygraph testing is not a

necessary or invariable part of sex-offender treatment). In sum, we are not

persuaded that any of these unpronounced additions to Condition Six could be

reasonably characterized as merely clarifying terms or basic administrative

requirements.

      Having found that the challenged additions to the written judgment

should have been pronounced at sentencing, we turn to the question of the

appropriate remedy. The government argues that we should remand to the

district court for the limited purpose of orally pronouncing the challenged

additions in Rosado’s presence and giving Rosado an opportunity to object. See

Appellee’s Post-Argument Letter Br., United States v. Rosado, No. 22-1013, ECF

No. 115 (Dec. 22, 2023). In some circumstances, we have granted this or a similar

remedy, even though the typical rule is that unpronounced conditions must be



                                        11
stricken from the judgment upon remand. Compare United States v. Handakas, 

 (2d Cir. 2003) and United States v. DeMartino, 

 (2d

Cir. 1997) with Washington, 

; Rosario, 

; and United

States v. Jacques, 

 (2d Cir. 2003). 3 However, the government

advanced this argument for the first time at oral argument, despite Rosado

arguing in his briefing that the unpronounced conditions should be stricken.

Accordingly, we decline to now consider the government’s request. See, e.g.,

United States v. Greer, 

 (2d Cir. 2000) (declining to consider

arguments not raised in parties’ appellate briefs). 4 We, therefore, will not

diverge from the typical practice of striking unpronounced conditions.




3 Cf. also United States v. Schultz, 

 (5th Cir. 2023) (“Because the
written judgment and oral pronouncement conflict, we REMAND to the district
court to amend the written judgment to conform with the oral announcement.”);
United States v. Martinez, 

 (5th Cir. 2001) (per curiam)
(remanding to amend written judgment to remove unannounced condition of
supervised release).

4
 Moreover, the government fails to show that this is the kind of situation in
which this Court has previously granted the remedy that it now seeks. See, e.g.,
Handakas, 

 (remanding for pronouncement when the
challenged condition had been previously properly imposed at the defendant’s
original sentencing); DeMartino, 

 (declining to conform the
written judgment to the orally pronounced sentence where district court had
failed to provide an adequate explanation for the sentence and where doing so
would potentially result in sentencing error).
                                          12
      We recognize that this decision may, at first glance, appear to be overly

formalistic, and striking conditions simply because they were not pronounced at

sentencing may seem to be a somewhat drastic remedy. However, the

requirement that a district court pronounce a sentence—including the conditions

of supervised release—in the presence of a defendant is an important one. As we

have observed, sentencing requires courts “to carefully balance the goals of

supervised release while remaining mindful of the life-altering effects their

judgments have on defendants, their families, and their communities.” Sims, 

. There is rarely a more significant occasion for a defendant or his

family than when his sentence is announced in open court. That occasion

permits the defendant and counsel not only to hear the sentence, but also to

object, to propose changes, or to seek clarification. That opportunity is lost if a

defendant does not know what punishments and restrictions he will be subjected

to until he later reads the written judgment. Consequently, the pronouncement

requirement is not a mere formality; it is an essential component of the

sentencing process.




                                         13
                                 CONCLUSION

      For the reasons set forth above, we VACATE and REMAND to the district

court with instructions to amend the written judgment to strike all of the

challenged portions of Conditions Three, Four, and Six. 5




5
 Because we conclude that the challenged portions of the conditions must be
stricken, we need not reach Rosado’s remaining arguments as to why these
conditions were impermissible.
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