22-1355-cr
United States v. Arguedas




                                    In the
             United States Court of Appeals
                       For the Second Circuit


                              August Term, 2023
                               No. 22-1355-cr

                        UNITED STATES OF AMERICA,
                                 Appellee,

                                        v.

            ALEXANDER ARGUEDAS, AKA SEALED DEFENDANT 1,
                        Defendant-Appellant. *



 On Appeal from a Judgment of the United States District Court for
               the Southern District of New York.



                         SUBMITTED: APRIL 11, 2024
                          DECIDED: APRIL 9, 2025

           Before: JACOBS, NARDINI, AND MENASHI, Circuit Judges.




       * The Clerk of Court is respectfully directed to unconsolidate Defendant-
Appellant Mark Brock’s appeal, No. 22-543, which has been resolved separately,
see United States v. Brock, No. 22-1355-CR, 

 (2d Cir. May 7, 2024)
(summary order), and to amend the official caption of this case as set forth above.
       Defendant-Appellant Alexander Arguedas pled guilty
pursuant to a plea agreement in the United States District Court for
the Southern District of New York to a racketeering conspiracy, a
narcotics conspiracy, and using and carrying firearms in furtherance
of a narcotics conspiracy. The district court (Jesse M. Furman, District
Judge) imposed a below-Guidelines sentence of 390 months of
imprisonment, to be followed by five years of supervised release, and
a special assessment of $300. The district court also imposed
mandatory, standard, and special conditions of supervised release.
       Arguedas appealed. His appellate counsel has now moved to
be relieved and for appointment of substitute counsel, and submitted
a brief in accordance with Anders v. California, 

 (1967). In
response, the government has moved to dismiss the appeal as barred
by an appeal waiver contained in the plea agreement or, in the
alternative, for summary affirmance.
       Despite appellate counsel’s diligence, the Anders brief is
incomplete because it does not address Arguedas’s conditions of
supervised release, which fall outside the scope of the appeal waiver.
Such a deficiency in an Anders brief, however, is not necessarily fatal
to a lawyer’s motion to withdraw. We hold that we may nevertheless
grant counsel’s motion to be relieved when a deficiency in the Anders
brief is harmless. Where counsel fails to address aspects of the
sentence not covered by the appeal waiver, that deficiency: (1) is
harmless when we can determine from the record that there are no
non-frivolous issues to raise regarding the aspects of the sentence not
covered by the appeal waiver; or (2) can be cured if counsel represents
that he has discussed with the defendant the potential benefits and
risks of challenging those aspects of the sentence that fall outside the
appeal waiver, and that the defendant has authorized counsel not to
pursue an appeal with regard to those matters.
       Applying the harmlessness analysis here, we conclude that
there are no non-frivolous issues with respect to the mandatory,




                                   2
standard, and five of the seven special conditions of supervised
release, and that appellate counsel’s failure to address those
conditions in the Anders brief is therefore harmless. However, the two
remaining special conditions concerning financial disclosure and new
lines of credit potentially raise non-frivolous issues for appeal.
Accordingly, we defer decision on the motions and order the parties
to file supplemental briefing.

                          Brandon D. Harper, Assistant United States
                          Attorney, for Matthew Podolsky, Acting
                          United States Attorney for the Southern
                          District of New York, New York, NY, for
                          Appellee.

                          Lucas Anderson, Rothman, Schneider,
                          Soloway & Stern, LLP, New York, NY, for
                          Defendant-Appellant Alexander Arguedas.


WILLIAM J. NARDINI, Circuit Judge:

       Defendant-Appellant Alexander Arguedas pled guilty
pursuant to a plea agreement in the United States District Court for
the Southern District of New York to (1) a racketeering conspiracy, in
violation of 

(d), (2) a conspiracy to distribute
narcotics, in violation of 

 and 841(b)(1)(A), and
(3) using and carrying firearms in furtherance of a narcotics
conspiracy, in violation of 

(c)(1)(A)(i) and 2. The plea
agreement includes an appeal waiver under which Arguedas agreed
to waive his right to challenge “any sentence within or below the
[advisory range under the United States Sentencing] Guidelines,”
“any term of supervised release that is less than or equal to the
statutory maximum,” “any fine that is less than or equal to




                                     3
$10,000,000,” and “any special assessment that is less than or equal to
$300.” App’x at 96–97.

      The district court (Jesse M. Furman, District Judge) imposed a
below-Guidelines sentence of 390 months of imprisonment, to be
followed by five years of supervised release, and a special assessment
of $300. The district court also imposed mandatory, standard, and
special conditions of supervised release. The district court declined
to impose a fine and deferred entry of an order of restitution.

      Arguedas appealed. His appellate counsel has now moved to
be relieved and for appointment of substitute counsel, and submitted
a brief in accordance with Anders v. California, 

 (1967). In
the Anders brief, appellate counsel argued that there are no non-
frivolous grounds for an appeal of Arguedas’s conviction. Appellate
counsel addressed various aspects of Arguedas’s conviction and
sentence but did not mention his conditions of supervised release. In
response, the government has moved to dismiss the appeal on the
basis that the appeal waiver is enforceable and bars Arguedas’s
appeal.   Alternatively, the government has moved for summary
affirmance of the conviction, arguing that there are no non-frivolous
issues for appeal.

      Despite appellate counsel’s diligence, the Anders brief is
incomplete. As we have recently clarified, an Anders brief in a case
involving an appeal waiver must, among other things, examine “the
scope of an appeal waiver and determin[e] whether there are non-
frivolous issues for appeal regarding sentencing components
arguably not covered by the waiver.” United States v. Reyes-Arzate, 91



                               

, 622 (2d Cir. 2024).         Here, Arguedas’s conditions of
supervised release fall outside the scope of the appeal waiver and
therefore appellate counsel’s failure to address those conditions
renders the Anders brief incomplete.

      We hold that such a deficiency in the Anders brief is not
necessarily fatal to a lawyer’s motion to withdraw: we may
nevertheless grant counsel’s motion to be relieved when a deficiency
in the Anders brief is harmless. Where counsel fails to address aspects
of the sentence not covered by the appeal waiver, that deficiency:
(1) is harmless when we can determine from the record that there are
no non-frivolous issues to raise regarding the aspects of the sentence
not covered by the appeal waiver; or (2) can be cured if counsel
represents that he has discussed with the defendant the potential
benefits and risks of challenging those aspects of the sentence that fall
outside the appeal waiver, and that the defendant has authorized
counsel not to pursue an appeal with regard to those matters.

      Applying the harmlessness analysis here, we conclude that
there are no non-frivolous issues with respect to the mandatory,
standard, and five of the seven special conditions of supervised
release, and that appellate counsel’s failure to address those
conditions in the Anders brief is therefore harmless. However, the two
remaining special conditions concerning financial disclosure and new
lines of credit potentially raise non-frivolous issues for appeal. We
thus cannot conclude that appellate counsel’s failure to address those
two conditions is harmless. Accordingly, we defer decision on the
motions and order the parties to file supplemental briefing.




                                   5
I.    Background

      A. Criminal Conduct and Subsequent Indictment

      From at least 2011 through March 2020, Arguedas was a part of
the Black Stone Gorilla Gang (“BSGG”), a subset of the Bloods gang
that operates in the New York City metropolitan area as well as New
York State jails and prisons. BSGG engaged in, among other things,
acts involving narcotics trafficking, bank fraud, wire fraud, murder,
assault, and robbery. Arguedas was not merely a member of the
BSGG; he also held several leadership roles and eventually served as
a “Godfather” between 2017 and 2020, which is the highest position
in the organization outside prison. As a Godfather, Arguedas had the
power to initiate new members into BSGG, discipline BSGG members,
and order and authorize violent acts against rival gang members.

      Throughout his involvement with the BSGG, Arguedas took
numerous acts in furtherance of the organization’s goals.          For
example, he assaulted a number of people, commissioned or assisted
violent acts against rival gang members, and participated in BSGG’s
narcotics trafficking scheme. He also murdered a rival drug dealer,
Gary Rodriguez, in a dispute over drug territory.

      On March 30, 2021, a grand jury returned a superseding
indictment that charged Arguedas and other BSGG members with
multiple counts arising from their conduct in the BSGG. Arguedas
was charged with ten counts:




                                 6
• Count One: racketeering conspiracy, in violation of 

(d);

• Count Two: murder in aid of racketeering, in violation of
  

(a)(1) and 2;

• Count Three: murder through the use of a firearm, in
  violation of 

(j) and 2;

• Count Four: conspiracy to commit murder in aid of
  racketeering and conspiracy to assault with a dangerous
  weapon in aid of racketeering, in violation of 

(a)(5) and (a)(6);

• Count Five: assault with a dangerous weapon and
  attempted murder in aid of racketeering, in violation of
  

(a)(3), 1959(a)(5), and 2;

• Count Six: use of a firearm in furtherance of assault with
  a dangerous weapon and attempted murder, in violation
  of 

(c)(1)(A)(i), (ii), (iii), and 2;

• Count Seven: attempted assault with a dangerous
  weapon in aid of racketeering, in violation of 

(a)(6) and 2;

• Count Eight: assault with a dangerous weapon in aid of
  racketeering, in violation of 

(a)(3) and 2;

• Count Nine: participation in a narcotics conspiracy, in
  violation of 

 and 841(b)(1)(A), (b)(1)(C),
  and (b)(1)(D); and




                         7
          • Count Ten: possession of firearms in furtherance of a
            narcotics conspiracy, in violation of 

(c)(1)(A)(i) and 2.

      B. Guilty Plea

      Arguedas and the government negotiated a plea agreement to
resolve his charges. Arguedas would plead guilty to Counts One
(racketeering conspiracy), Nine (narcotics conspiracy), and Ten
(possession of a firearm in furtherance of a narcotics conspiracy).
Arguedas would also admit that he participated in the murder of
Rodriguez in furtherance of the BSGG’s goals.          In exchange, the
government would dismiss the remaining counts against Arguedas
and refrain from further prosecution of Arguedas for certain crimes.

      The parties stipulated in the plea agreement that the advisory
Guidelines range was a term of imprisonment of 420 months to life,
with a statutory minimum of 180 months of imprisonment. The
stipulated Guidelines range was based on a total offense level of 40
and a criminal history category of VI. In calculating the total offense
level, the parties used the following two predicate offenses: the
murder of Rodriguez and drug trafficking. The parties classified
Arguedas as a career offender under U.S.S.G § 4B1.1 because he had
two prior state felony convictions for attempted robbery. Arguedas’s
status as a career offender did not affect his total offense level, but it
did increase his criminal history category from V to VI.

      The plea agreement also included an appeal waiver. Arguedas
agreed to forgo his right to bring a direct appeal or collateral challenge




                                    8
“of any sentence within or below the Stipulated Guidelines Range,”
“any term of supervised release that is less than or equal to the
statutory maximum,” “any fine that is less than or equal to
$10,000,000,” and “any special assessment that is less than or equal to
$300.” App’x at 96–97. The government reciprocally agreed to forgo
any appeal of a “sentence within or above the Stipulated Guidelines
Range,” and any appeal or collateral challenge to a “fine that is greater
than or equal to $50,000.” Id. at 97.

      On February 8, 2022, Arguedas appeared before a magistrate
judge (Debra C. Freeman, Magistrate Judge) and, pursuant to the plea
agreement, pled guilty to Counts One, Nine, and Ten. During the
hearing, the magistrate judge informed Arguedas of his rights and the
effects of his guilty plea. For instance, the magistrate judge reviewed
with Arguedas the rights that he would waive by pleading guilty and
the contents of the plea agreement, specifically confirming with
Arguedas that he discussed the plea agreement with his counsel and
that he understood the appeal waiver. The magistrate judge also
reviewed with Arguedas the statutory penalties associated with the
plea including the mandatory minimum prison term of fifteen years
(five of which must be served consecutively to any other term of
imprisonment     imposed),    the   mandatory     minimum      term   of
supervised release of five years, and a possible order of restitution to
any victims of the crimes. And upon prompting from the magistrate
judge, the government explained the elements of Counts One, Nine,
and Ten. Furthermore, the magistrate judge canvassed Arguedas to
ensure that he entered the guilty plea competently and voluntarily




                                    9
and that there was a factual basis for the plea. Based on the colloquy
with Arguedas, the magistrate judge recommended that the district
judge accept Arguedas’s guilty plea. The district judge (Jed S. Rakoff,
District Judge) accepted the guilty plea on February 18, 2022.

      C. Sentencing

      Prior to sentencing, the U.S. Probation Office prepared the
Presentence Investigation Report (“PSR”). Consistent with the plea
agreement, the PSR determined the applicable Guidelines range to be
a term of imprisonment of 420 months to life, based on a total offense
level of 40 and a criminal history category of VI. The PSR’s calculation
of the Guidelines range was the same as that of the plea agreement,
except that the PSR factored in a prior conviction that the plea
agreement did not. That additional conviction, however, had no
impact on the resulting Guidelines range. The PSR also documented
Arguedas’s background and characteristics including his struggles
with mental health and his history of substance abuse.              The
government did not submit any objections to the PSR. Arguedas
objected to the inclusion of certain facts in the PSR but did not
challenge the accuracy of those facts.

      Additionally, included with the PSR was the Probation Office’s
sentencing recommendation in which it listed the mandatory and
standard conditions of supervised release as well as several proposed,
special conditions of supervised release.       The Probation Office
proposed the following special conditions:




                                  10
            • Special Condition #1: Arguedas must participate in an
              outpatient substance abuse treatment program;

            • Special Condition #2: Arguedas must provide any
              requested financial information to the probation officer;

            • Special Condition #3: Arguedas must refrain from
              opening new lines of credit without his probation
              officer’s approval, unless he complies with the
              installment payment schedule for any restitution or fine;

            • Special Condition #4: Arguedas must participate in an
              outpatient mental health treatment program;

            • Special Condition #5: Arguedas must submit himself to a
              reasonable search of his person, property, residence,
              vehicle, papers, computer, and any other electronic
              devices;

            • Special Condition #6: Arguedas must not associate with
              any gang members, particularly members of the Bloods
              gang, or frequent neighborhoods known to be controlled
              by the Bloods gang; and

            • Special Condition #7: Arguedas must be supervised by
              the district of his residence.

      On May 24, 2022, the district court (Jesse M. Furman, District
Judge) 2 sentenced Arguedas. At sentencing, Arguedas confirmed that
he had reviewed and discussed the PSR with his counsel. Neither
Arguedas nor the government disputed the accuracy of the facts or

      2   After the change of plea proceeding, the case was reassigned to Judge
Furman.




                                       11
the Guidelines calculations set forth in the PSR. The district court
subsequently adopted the facts and the Guidelines calculations in the
PSR.

       After remarks from the parties (including from Arguedas
himself), the district court addressed the sentencing factors under 

(a).   The district court explained that “a substantial
sentence is warranted” because Arguedas’s crimes and conduct—
murder, attempted murder, and other “really appalling acts of
violence”—“are among the most despicable there are.” App’x at 128–
29.    The district court pointed to videos in which Arguedas
documented his violent acts, stating that those videos “are deeply
disturbing” and suggest that Arguedas “is a danger to society.” Id. at
129.   The district court also discussed Arguedas’s “lengthy and
disturbing criminal history,” which includes “multiple convictions
for prior acts of violence” and offenses committed while on parole or
probation. Id. Weighing against the severity of Arguedas’s conduct
and criminal history, however, were several mitigating factors
identified by the district court such as Arguedas’s difficult upbringing
and the time that Arguedas had already spent in custody during the
COVID-19 pandemic, which made the conditions of confinement
harsher than normal.

       Relying on the reasons described above, the district court
imposed a slightly below-Guidelines sentence of 390 months of
imprisonment, to be followed by three years of supervised release,
and a special assessment of $300. In connection with the term of
supervised release, the district court imposed the mandatory,




                                  12
standard, and special conditions of supervised release proposed by
the Probation Office. The district court declined to impose a fine,
finding that Arguedas was unable to pay one. The government did
not seek forfeiture. Additionally, because the government had not
been able to reach any victims by the time of sentencing, the district
court deferred entry of an order of restitution for the statutory period
of ninety days under 

(d)(5) and directed the
government to submit a proposed order of restitution in the event it
determined that restitution was appropriate.         The government,
however, never sought an order of restitution after sentencing, and
the district court never imposed one.

      The district court entered judgment on May 25, 2022. The
written judgment accurately reflected the district court’s orally
imposed sentence except with respect to the term of supervised
release: the written judgment imposed the mandatory minimum five
years of supervised release as opposed to the three years orally
imposed by the district court at sentencing.

      D. Appeal

      On June 17, 2022, Arguedas filed a pro se notice of appeal, even
though he was still represented by counsel. In his notice, Arguedas
argued that he had received ineffective assistance of counsel and that
his guilty plea had not been knowingly, willingly, and intelligently
made. He noted that he attempted to file a notice of appeal within the
deadline to file an appeal under Federal Rule of Appellate Procedure
4(b), but a lockdown at his prison prevented him from doing so.




                                  13
       On December 27, 2022, defense counsel, who represented
Arguedas before the district court, moved to be relieved as counsel. 3
Defense counsel argued that such relief was necessary because
Arguedas’s allegations in his notice of appeal—that he had received
ineffective assistance of counsel and that his guilty plea was
improper—presented a conflict of interest. This Court granted the
motion on January 6, 2023, and directed Arguedas to file an
application for appointment of counsel pursuant to the Criminal
Justice Act, 18 U.S.C. § 3006A, if he wished to be represented by
counsel in this appeal. After Arguedas returned his application, this
Court appointed appellate counsel on January 26, 2023.

       On June 14, 2023, appellate counsel moved to be relieved as
counsel and for the appointment of substitute counsel. Appellate
counsel explained that he had notified Arguedas of his intent to
submit a brief in accordance with Anders v. California, 

(1967), based on his belief that no non-frivolous appellate issues
existed.    Appellate counsel further explained that he informed
Arguedas of his “right to: (1) do nothing; (2) request that the Court
provide [him] with substitute counsel; (3) hire a private attorney; (4)
submit pro se papers in support of [his] appeal; or (5) voluntarily
withdraw the appeal.” Dkt. 83, at 2–3. Appellate counsel conveyed
Arguedas’s desire for substitute counsel to be appointed.




       3 Before that motion, defense counsel filed multiple motions to be relieved
as counsel, the first of which was filed on August 23, 2022. This Court denied each
of those motions for noncompliance with Local Rule 4.1(d)(3).




                                        14
      On June 22, 2023, this Court denied appellate counsel’s motion
due to the lack of an Anders brief. Later on the same day, appellate
counsel renewed his request for the appointment of substitute counsel
and moved, in the alternative, for an extension of the briefing
deadline. Appellate counsel stated in the motion that he spoke to
Arguedas the day before and that Arguedas reiterated that “he does
not wish for [appellate counsel] to continue representing him.” Dkt.
88, at 2. On June 23, 2023, this Court granted appellate counsel’s
request for an extension of the briefing schedule.

      On July 13, 2023, appellate counsel filed an Anders brief
accompanied by a motion to be relieved as counsel and for
appointment of substitute counsel. In the Anders brief, appellate
counsel asserted that “there are no non-frivolous grounds for an
appeal of Arguedas’s conviction under Counts One, Nine, and/or
Ten.” Dkt. 96, at 20. After describing the plea proceeding, appellate
counsel argued that the proceeding complied with Federal Rule of
Criminal Procedure 11(b)(1), that Arguedas’s plea was voluntarily
made, and that there was a sufficient factual basis for Arguedas’s
guilty plea.    Appellate counsel further argued that Arguedas
knowingly and voluntarily waived his right to appeal his sentence
under the plea agreement. And even if Arguedas could challenge his
sentence, appellate counsel represented that he was able to identify
only one viable issue with respect to the sentence, which concerned
the application of the career offender designation for the Guidelines
range calculations. But appellate counsel stated that even if the career
offender designation did not apply to Arguedas, the Guidelines range




                                  15
would remain unchanged. Finally, appellate counsel noted that a
successful challenge to Arguedas’s conviction “would give rise to
‘unacceptable risk of a harsher sentence,’” given that he would be
subject to prosecution for the other crimes charged in the superseding
indictment. Dkt. 96, at 26 (quoting United States v. Ibrahim, 

 (2d Cir. 1995)).

      On October 12, 2023, the government moved to dismiss the
appeal, arguing that the appeal waiver is enforceable and bars
Arguedas’s appeal. In the alternative, the government moved for
summary affirmance of the conviction based on its belief that there
are no non-frivolous issues that can be raised on appeal. Appellate
counsel opposed the government’s motion, contending that dismissal
or summary affirmance are premature in light of Arguedas’s pending
motion to appoint substitute counsel.

      In a supplemental filing on December 5, 2023, appellate counsel
stated that during a recent phone call, “Arguedas confirmed that if
this Court does not grant his request for substitute counsel he will
wish to proceed pro se in lieu of having his appeal dismissed.” Dkt.
138, at 2 (emphasis omitted).

II.   Discussion

      Pending before us now are (1) appellate counsel’s motion to be
relieved and to appoint substitute counsel, and (2) the government’s
motion to dismiss or, in the alternative, for summary affirmance. For
the reasons below, we defer decision on the motions and order
supplemental briefing from the parties.



                                   16
      A. The Sufficiency of the Anders Brief

      “The well-established Anders procedure governs requests by
defense counsel to withdraw from an appeal if, after ‘conscientious
examination’ of the record, she determines the appeal ‘to be wholly
frivolous.’” Reyes-Arzate, 91 F.4th at 620 (quoting Anders, 

). Under this procedure, counsel must first file a motion to be
relieved accompanied by an Anders brief that discusses “anything in
the record that might arguably support the appeal.”            

 at 621
(quoting Anders, 

). Afterwards, the defendant may
“’raise any points that he chooses’ in a pro se appellate brief.” United
States v. Fleming, 

 (2d Cir. 2021) (quoting Anders, 

).

      Armed with “a properly prepared Anders brief,” Reyes-Arzate,
91 F.4th at 621 (quoting United States v. Kosic, 

, 451 (2d Cir.
2019)), we then conduct “a full examination” of the proceedings
below “to decide whether the case is wholly frivolous,” 

 (quoting
Anders, 

). Only after “we are satisfied that ‘counsel has
diligently searched the record for any arguably meritorious issue in
support of his client’s appeal,’ and that counsel’s characterization of
the appeal as ‘frivolous is, in fact, legally correct,’” may we grant a
counsel’s motion to be relieved. 

 (quoting United States v. 777
Greene Ave., 

 (2d Cir. 2010)).

      In cases involving an appeal waiver, such as here, we have
imposed specific requirements for an adequate Anders brief. It is not
enough for counsel to address only the enforceability of an appeal




                                    17
waiver because “no appeal waiver, even if valid, ‘serves as an
absolute bar to all appellate claims.’” Reyes-Arzate, 91 F.4th at 622
(quoting Garza v. Idaho, 

 (2019)). “[A] ‘valid and
enforceable appeal waiver . . . only precludes challenges that fall
within its scope.’” 

 (quoting Garza, 

). Thus, to
adequately assess whether any non-frivolous issues exist in such
cases, the Anders brief must address the following “limited issues”:

      (1) [W]hether defendant’s plea and waiver of appellate
      rights were knowing, voluntary, and competent; or (2)
      whether it would be against the defendant’s interest to
      contest his plea; and (3) any issues implicating a
      defendant’s constitutional or statutory rights that either
      cannot be waived, or cannot be considered waived by the
      defendant in light of the particular circumstances.

 at 621 (quoting United States v. Gomez-Perez, 

(2d Cir. 2000) (citations omitted)). Defense counsel’s obligation to
address the third issue “includes examining the scope of an appeal
waiver and determining whether there are non-frivolous issues for
appeal regarding sentencing components arguably not covered by the
waiver.”   Id. at 622.    In other words, “when defense counsel
determines that an appeal waiver covers only part of a sentence,
counsel must separately address the procedural and substantive
reasonableness of the non-covered components.” Id.

      Here, appellate counsel thoroughly addressed in the Anders
brief the validity of Arguedas’s guilty plea, the enforceability of the
appeal waiver, any non-frivolous issues with respect to Arguedas’s




                                  18
term of imprisonment, and whether it is in Arguedas’s best interest to
challenge the conviction. And upon a careful review of the record,
we agree with appellate counsel that Arguedas entered into his plea
knowingly, voluntarily, and competently, and that the appeal waiver
is valid and enforceable.     Because the appeal waiver is valid,
Arguedas is barred from challenging his term of imprisonment, his
term of supervised release, and the special assessment, all of which
fall within the scope of the appeal waiver.

      The Anders brief, however, is incomplete because it fails to
address components of the sentence that fall outside the appeal
waiver. The district court imposed mandatory, standard, and special
conditions of supervised release, none of which are mentioned in the
Anders brief. Under the appeal waiver, Arguedas waived his right to
challenge “any term of supervised release that is less than or equal to
the statutory maximum,” App’x at 97 (emphasis added), but he did
not waive his right to appeal the conditions of supervised release. See
United States v. Burden, 

 (2d Cir. 2017) (“[W]hen an
appeal waiver is silent regarding a specific aspect of a sentence, this
Court generally finds that the appeal waiver does not foreclose
challenges to that aspect of the sentence.” (internal quotation marks
omitted)). Consequently, the absence of discussion of the conditions
of supervised release renders the Anders brief incomplete. See Reyes-
Arzate, 91 F.4th at 622–23 (concluding that the Anders brief was
deficient because it did not address aspects of the sentence, such as
the conditions of supervised release, that fell outside of the appeal
waiver).




                                  19
      B. Harmlessness

      Our finding that the Anders brief is incomplete does not end our
inquiry. Such a deficiency in the Anders brief is not necessarily fatal
to a lawyer’s motion to withdraw. We may nevertheless grant
counsel’s motion to be relieved when the gap in an Anders brief is
harmless.   Where an Anders brief fails to address aspects of the
sentence not covered by the appeal waiver, that omission: (1) is
harmless when we can determine from the record that there are no
non-frivolous issues to raise regarding the aspects of the sentence not
covered by the appeal waiver; or (2) can be cured if counsel represents
that he has discussed with the defendant the potential benefits and
risks of challenging those aspects of the sentence that fall outside the
appeal waiver, and that the defendant has authorized counsel not to
pursue an appeal with regard to those matters.

      It is often the case that a defendant has no desire to challenge
particular portions of his sentence or conviction.      Most criminal
appeals following guilty pleas focus exclusively on the length of the
prison sentence imposed, leaving the remainder of the judgment
untouched. This is unsurprising, given that incarceration is usually
the greatest imposition on a defendant’s liberty that stems from a
criminal sentence. So it is possible that a particular defendant may
have no interest in challenging aspects of his sentence that are not
covered by an appeal waiver. In such circumstances, counsel who
submits an Anders brief may indicate that he has discussed with the
defendant the potential benefits and risks of challenging those
specified aspects of the sentence that fall outside the appeal waiver,




                                  20
and that the defendant has authorized counsel not to pursue an
appeal with regard to those matters. An Anders brief that includes
such a representation would be sufficient and without defect.

      In this case, however, appellate counsel has not yet had an
opportunity to determine, in line with our direction above, whether
Arguedas wishes to challenge his conditions of supervised release.
We thus consider whether the omission of this discussion from the
Anders brief can be disregarded as harmless.

      We begin by explaining why review for harmlessness is
appropriate here.     We have previously held that “we may not
independently determine the merits of an appeal, absent a properly
prepared Anders brief.” United States v. Burnett, 

 (2d
Cir. 1993). This is because the Anders procedure is meant “to vindicate
the [defendant’s] constitutional right to appellate counsel.” Smith v.
Robbins, 

 (2000). Without a proper Anders brief, there
is no guarantee that a defendant was afforded “a diligent and
thorough review of the record and an identification of any arguable
issues revealed by that review.” United States v. Whitley, 

 (2d Cir. 2007) (quoting McCoy v. Court of Appeals of Wisconsin, 

 (1988)); see also Burnett, 

 (“Acceptance of a
non-conforming Anders brief is akin to a constructive denial of
counsel.”). Judicial review of the merits of the case “is no substitute
for [the sort of] adversary representation” promised under the Sixth
Amendment. United States v. Zuluaga, 

 (2d Cir. 1992).




                                   21
      We have applied that principle—that we may not determine
the merits of an appeal without an adequate Anders brief—in a series
of cases where counsel submitted wholly deficient Anders briefs. For
example, in United States v. Zuluaga, counsel’s Anders brief was devoid
of any analysis—the argument section contained three conclusory
sentences. 

. Similarly, in United States v. Burnett, counsel
submitted an “Anders brief consisting solely of one and a half pages
of argument” (despite there being 787 pages of trial transcripts) that
failed to address critical issues raised during trial. 

. In
United States v. Whitley, counsel’s Anders briefs failed to address the
reasonableness of the defendants’ sentences. 

. And in
United States v. Urena, counsel failed to “identify possible issues for
appeal []or discuss the sentencing transcript to demonstrate why no
such issue exists,” providing only “conclusory assertions.” 

, 708–09 (2d Cir. 1994). Counsel in Urena also failed to include
sentencing transcripts and the plea agreement in the appendices to
their briefs, further demonstrating that counsel did not “search the
record with care.” 

.

      In contrast, appellate counsel’s Anders brief here is far from
wholly deficient and therefore does not raise the same concerns
regarding a defendant’s right to counsel. Appellate counsel’s Anders
brief rigorously examines the change of plea proceeding, the term of
imprisonment, and the appeal waiver. Appellate counsel explains
why no meritorious issues exist, often providing citations to the
record in support of his explanation. The brief also assesses whether
it is in the best interest of Arguedas to proceed with an appeal. Along




                                   22
with the brief, appellate counsel submitted an appendix, which
includes relevant transcripts from district court proceedings, the plea
agreement, and the judgment. Appellate counsel’s only mistake is his
failure to address Arguedas’s conditions of supervised release, which
amounts to merely a minor deficiency in this particular Anders brief.

          In short, the brief was “properly prepared” though incomplete.
It   is    clear   from   appellate   counsel’s   submissions    that   he
conscientiously scoured the record for any non-frivolous issues for
appeal. Because the brief was diligently prepared, this is not a case in
which a defective Anders brief “amounts to a constructive denial of
counsel.” United States v. Zuluaga, 

 (2d Cir. 1992). Only
the “[a]ctual or constructive denial of the assistance of counsel
altogether is legally presumed to result in prejudice.” Strickland v.
Washington, 

 (1984) (emphasis added).           When a
defendant receives the assistance of counsel but that assistance may
have been deficient—as, by analogy, the incomplete Anders brief was
here—we        consider   whether     “any   deficiencies   in   counsel’s
performance [were] prejudicial to the defense” before concluding the
assistance was ineffective. 

 In accordance with that framework, we
find review for harmlessness appropriate here and turn to determine
whether there are any non-frivolous issues to raise related to the
conditions of supervised release.

          We generally “review the imposition of conditions of
supervised release for abuse of discretion,” United States v. Eaglin, 

 (2d Cir. 2019). “When[, as here,] the defendant does not
object to the conditions,” we review for plain error. United States v.




                                      23
Green, 

 (2d Cir. 2010); see also Fed. R. Crim. P. 52(b).
“Under plain error review, an appellant must demonstrate that ‘(1)
there is an error; (2) the error is clear or obvious, rather than subject
to reasonable dispute; (3) the error affected the appellant’s substantial
rights, which in the ordinary case means it affected the outcome of the
district court proceedings; and (4) the error seriously affects the
fairness, integrity or public reputation of judicial proceedings.’”
United States v. Napout, 

 (2d Cir. 2020) (quoting United
States v. Marcus, 

 (2010) (brackets and internal
quotation marks omitted)).

      We have applied “a ‘relaxed’ form of plain error review in those
rare cases in which the defendant lacked sufficient prior notice that a
particular condition of supervised release might be imposed.” United
States v. Matta, 

 (2d Cir. 2015). For example, we have
applied the relaxed plain error standard where the defendant first
learned of the challenged condition of supervised release from the
written judgment. See 

. We have also applied that standard
when the defendant was aware of the challenged condition from the
PSR, but the district court’s oral pronouncement of the condition led
the defendant to believe that a different condition would be imposed
than the one described in the PSR and then the written judgment. See
United States v. Washington, 

, 207–08 (2d Cir. 2018).

      That standard is inappropriate here because Arguedas had
sufficient notice of the conditions of supervised release from the
district court’s oral pronouncement but failed to object to them.
Indeed, here Arguedas was alerted of the potential imposition of




                                   24
these conditions even before the hearing began. The PSR listed the
mandatory, standard, and special conditions that were later imposed
by the district court. At sentencing, Arguedas confirmed that he
reviewed and discussed the PSR with his counsel. And when the
district court orally imposed those conditions, its recitation of the
conditions did not deviate from the PSR: it described the mandatory
conditions of supervised release just as they appear in the PSR, and it
referenced the pages of the PSR with the standard and special
conditions of supervised release, effectively incorporating them by
reference. Cf. United States v. Rosado, 

, 124 & n.2 (2d Cir.
2024) (holding the district court did not sufficiently incorporate
special conditions in the PSR at sentencing where: (i) it did not
explicitly refer to the PSR; and (ii) the conditions as orally pronounced
were materially different). The conditions of supervised release set
forth in the written judgment are consistent with the PSR and the
district court’s oral pronouncement.

      “[O]ur caselaw is clear that traditional plain-error review
applies when, as here, a defendant has notice that a condition of
supervised release will be imposed and fails to object.” United States
v. Lewis, 

 (2d Cir. 2025). Accordingly, relaxation of the
plain error standard is not warranted. See also United States v. Dupes,

, 343 n.2 (2d Cir. 2008). We therefore review the district
court’s imposition of the conditions of supervised release under the
traditional plain error standard.

      “Under 

(d), the imposition of certain conditions
of supervised release is mandatory, but district courts also have




                                    25
discretion to impose other, non-mandatory conditions of supervised
release, which are commonly referred to as ‘special conditions.’”
United States v. Kunz, 

 (2d Cir. 2023) (quoting United
States v. Browder, 

 (2d Cir. 2017)). “That discretion is
constrained by 

(d)(1) and Sentencing Guidelines
§ 5D1.3(b), which each require, among other things, that the special
conditions be ‘reasonably related’ to familiar sentencing factors,”
“involve ‘no greater deprivation of liberty than is reasonably
necessary’ to achieve those purposes,” and “be ‘consistent with any
pertinent policy statements issued by the Sentencing Commission.’”
Id. (quoting 

(d)(2)-(3) and U.S.S.G. § 5D1.3(b)).
Sentencing factors include “‘the nature and circumstances of the
offense and the history and characteristics of the defendant’; ‘the need
for the sentence imposed to afford adequate deterrence to criminal
conduct’; ‘the need to protect the public from further crimes of the
defendant’; and ‘the need to provide the defendant with needed
educational or vocational training, medical care, or other correctional
treatment in the most effective manner.’” United States v. Betts, 

 (2d Cir. 2018) (quoting U.S.S.G. § 5D1.3(b)).

      Additionally, “[a] district court is required to make an
individualized assessment when determining whether to impose a
special condition of supervised release, and to state on the record the
reason for imposing it; the failure to do so is error.” Id. “In the
absence of such an explanation, we may uphold the condition
imposed only if the district court’s reasoning is ‘self-evident in the




                                   26
record.’” Id. (quoting United States v. Balon, 

, 41 n.1 (2d Cir.
2004)).

      Applying the harmlessness analysis here, we conclude that
there are no non-frivolous issues with respect to the mandatory,
standard, and five of the seven special conditions of supervised
release (Special Conditions #1, #4, #5, #6, and #7). However, the two
remaining special conditions concerning financial disclosure and new
lines of credit (Special Conditions #2 and #3, respectively) potentially
raise non-frivolous issues.

            i.   Mandatory and Standard Conditions of Supervised
                 Release

      We first hold that the district court did not err, let alone plainly
err, by imposing the mandatory and standard conditions of
supervised release.     Those conditions “are basic administrative
requirements, generally imposed by sentencing courts, and plainly
appropriate to implement supervised release.”            United States v.
Jacques, 

 (2d Cir. 2003). Appellate counsel’s failure to
address the mandatory and standard conditions of supervised release
in the Anders brief is therefore harmless.

           ii.   Special Conditions #1, #4, #5, #6, and #7

      Next, we discern no error in the district court’s imposition of
the special conditions of supervised release pertaining to substance
abuse treatment, mental health treatment, search, non-association
with gang members, and supervision by the district of residence.




                                    27
Although the district court did not articulate its reasons for imposing
these special conditions, we find that its reasons are “self-evident in
the record,” Betts, 

, and that those conditions are
reasonably related to the pertinent sentencing factors. We address
each of those special conditions below.

      The district court imposed Special Conditions #1 and #4, which
require Arguedas to submit to substance abuse treatment and mental
health treatment.     Those conditions are reasonably related to
Arguedas’s characteristics in light of his extensive history of
substance abuse and struggles with mental health. See, e.g., United
States v. Chaklader, 

 (2d Cir. 2000) (upholding
substance abuse program condition where defendant had substance
abuse history).

      The district court also imposed Special Condition #5,
mandating Arguedas to submit to a search by the probation officer of
his person, property, residence, vehicle, papers, computer, and any
other electronic devices, if there is reasonable suspicion that
Arguedas violated a condition of supervised release or committed
unlawful acts. That condition is reasonably related to the nature of
the offense, and it serves the goals of adequate deterrence and
protecting the public from further crimes of the defendant. During
sentencing, the district court expressed its concern with Arguedas’s
criminal history—characterizing it as “lengthy and disturbing”—and
with the fact that the crimes for which Arguedas was being sentenced
consisted of “appalling acts of violence.”     App’x at 129.    Those
characterizations are well-founded in the record, which shows that




                                  28
(1) Arguedas’s criminal history spanned over a decade and involved,
inter alia, assaults, robberies, and possession of a dangerous weapon;
and (2) Arguedas’s conduct leading up to this conviction involved
murder, attempted murder, and numerous violent assaults, as well as
drug trafficking and possession of firearms.

      Given the severity of Arguedas’s conduct and his penchant for
re-offending, the need to deter and protect the public is especially
acute. These reasons alone justify imposition of Special Condition #5
in its entirety. Lest there be any doubt about the appropriateness of
this condition, including the electronic search provision, the record
reveals that Arguedas used electronic devices to document a number
of his assaults and to commission violent acts against rival gang
members. To be clear, we do not suggest that such record evidence is
required for a district court to impose an electronic search condition;
we merely describe that evidence to illustrate the district court’s well-
founded concern about the use of electronic devices. The district
court therefore did not err by imposing the search condition.

      Further, the district court imposed Special Condition #6, which
prohibits Arguedas from associating with any gang members,
particularly   members     of   the        Bloods   gang,   or   frequenting
neighborhoods known to be controlled by the Bloods gang. The
district court’s reason for imposing such a condition is self-evident
based on the record. Arguedas admitted during the plea proceeding
that he was “associated” with the BSGG, a subset of the Bloods gang,
and there was ample evidence that his association with the BSGG was
directly related to the crimes of conviction. See United States v. Bolin,




                                      29


, 211–12 (2d Cir. 2020) (finding a special condition
prohibiting a defendant from associating with white supremacists
was reasonably related to sentencing objectives, where the
defendant’s online activity praising white supremacy eventually led
to the defendant making a fraudulent representation to government
agents); cf. United States v. Sims, 

, 126–29 (2d Cir. 2024)
(concluding that it was not self-evident from the record why the
district court imposed a condition prohibiting a defendant from
associating with any gang members, where the defendant had never
been charged with a crime related to any gang).

      The district court imposed Special Condition #7, which requires
Arguedas to be supervised by the district of his residence. This
condition is “clearly [a] ‘basic administrative requirement’ that [is]
‘necessary to supervised release’” and “provide[s] essential details for
[the defendant’s] compliance with the enumerated standard
conditions,” United States v. Thomas, 

 (2d Cir. 2002)
(alteration omitted) (quoting United States v. Truscello, 

 (2d Cir. 1999)), which are “are presumed suitable in all cases,”
United States v. Asuncion-Pimental, 

 (2d Cir. 2002). The
district court therefore did not err by imposing Special Condition #7.

      In sum, appellate counsel’s failure to address Special
Conditions #1, #4, #5, #6, and #7, is harmless because there are no non-
frivolous issues stemming from those conditions.




                                   30
            iii.   Special Conditions #2 and #3

         Finally, we conclude that the remaining two special conditions
of supervised release, Special Conditions #2 and #3, potentially raise
non-frivolous issues for appeal.        Special Condition #2 requires
Arguedas to “provide the probation officer with access to any
requested financial information.” App’x at 141. The Sentencing
Guidelines recommend the financial disclosure condition when the
district court orders restitution, forfeiture, or payment of a fine.
U.S.S.G. § 5D1.3(d)(3). Special Condition #3 prohibits Arguedas from
“incur[ring] new credit charges or open[ing] additional lines of credit
without the approval of the probation officer unless [he is] in
compliance with the installment payment schedule.” App’x at 141.
The Sentencing Guidelines recommend this condition when the
district court imposes restitution or a fine. U.S.S.G. § 5D1.3(d)(2).

         Here, the district court did not impose any of the financial
obligations described above that warrant Special Conditions #2 and
#3. The district court did not impose a fine, and the government did
not seek forfeiture in this case.       Additionally, the district court
deferred entry of an order of restitution and directed the government
to file a proposed order of restitution if the government determined
that restitution was appropriate. But the government never filed a
proposed order, and the district court ultimately did not impose an
order of restitution. It is not clear whether the district court intended
to impose Special Conditions #2 and #3 given the lack of a restitution
order.




                                   31
       Because the district court did not impose any of the financial
obligations that typically demand special conditions concerning the
defendant’s financial fitness, Special Conditions #2 and #3 potentially
raise non-frivolous issues for appeal. We therefore cannot conclude
that appellate counsel’s failure to address these conditions in the
Anders brief is harmless.     Accordingly, supplemental briefing is
required, and we defer decision on appellate counsel’s motion to
withdraw and to appoint substitute counsel, and the government’s
motion to dismiss or, in the alternative, for summary affirmance.

III.   Conclusion

       In sum, we hold as follows:

       1. Appellate counsel’s Anders brief is incomplete because it
          fails to address components of the sentence that fall outside
          the appeal waiver, specifically Arguedas’s conditions of
          supervised release.

       2. We may nevertheless grant counsel’s motion to be relieved
          when a deficiency in the Anders brief is harmless. Where
          counsel fails to address aspects of the sentence not covered
          by the appeal waiver, that deficiency: (1) is harmless when
          we can determine from the record that there are no non-
          frivolous issues to raise regarding the aspects of the sentence
          not covered by the appeal waiver; or (2) can be cured if
          counsel represents that he has discussed with the defendant
          the potential benefits and risks of challenging those aspects
          of the sentence that fall outside the appeal waiver, and that
          the defendant has authorized counsel not to pursue an
          appeal with regard to those matters.




                                   32
      3. Applying the harmlessness analysis here, we conclude that
         there are no non-frivolous issues with respect to the
         mandatory, standard, and five of the seven special
         conditions of supervised release, and that appellate
         counsel’s failure to address those conditions in the Anders
         brief is therefore harmless. However, the two remaining
         special conditions concerning financial disclosure and new
         lines of credit potentially raise non-frivolous issues for
         appeal. Thus, we cannot conclude that appellate counsel’s
         failure to address those two conditions is harmless.

      Accordingly, we DEFER decision on the motions. Within 30
days of this opinion, appellate counsel must file a supplemental brief
addressing whether Arguedas wishes to appeal Special Conditions #2
and #3.     If Arguedas does not wish to appeal those conditions,
appellate counsel may indicate that he has discussed with Arguedas
the potential benefits and risks of challenging those special conditions
and that Arguedas has authorized counsel not to pursue an appeal
with regard to those matters. But if Arguedas does wish to proceed
with such an appeal, counsel must also address whether those
conditions raise any non-frivolous issues for appeal.        Appellate
counsel’s supplemental brief may address any other issues he deems
relevant.

      Within 30 days of the filing of appellate counsel’s supplemental
briefing, the government is directed to submit a response. If appellate
counsel represents that Arguedas does wish to appeal Special
Conditions #2 and #3 and argues that those conditions raise non-




                                  33
frivolous issues for appeal, the government may respond by
addressing those conditions and stating whether remand to the
district court is necessary.     After appellate counsel and the
government file supplemental briefing, both the Anders motion and
the government’s motion to dismiss and/or for summary affirmance
will be decided by this panel.




                                 34