 United States Court of Appeals
         FOR THE DISTRICT OF COLUMBIA CIRCUIT



Argued January 18, 2018                Decided May 1, 2018

                        No. 17-3039

                UNITED STATES OF AMERICA,
                        APPELLEE

                             v.

                      JOHN HAN LEE,
                        APPELLANT


        Appeal from the United States District Court
                for the District of Columbia
                   (No. 1:13-cr-00081-1)


    A.J. Kramer, Federal Public Defender, argued the cause
and filed the briefs for appellant.

     Luke M. Jones, Assistant U.S. Attorney, argued the cause
for appellee. With him on the brief were Jessie K. Liu, U.S.
Attorney, and Elizabeth Trosman, Nicholas P. Coleman, and
Michael K. Atkinson, Assistant U.S. Attorneys.

    Before: HENDERSON, ROGERS, and KAVANAUGH, Circuit
Judges.

    Opinion for the Court filed by Circuit Judge KAVANAUGH,
with whom Circuit Judge HENDERSON joins.
                               2
    Dissenting opinion filed by Circuit Judge ROGERS.

     KAVANAUGH, Circuit Judge: When a defendant enters
into a plea agreement with the Government, the defendant may
agree to waive the right to appeal the sentence. At the
defendant’s subsequent plea hearing, the district court must
ensure that the defendant understands that appeal waiver. In
particular, Rule 11(b)(1)(N) of the Federal Rules of Criminal
Procedure requires the district court, at the plea hearing, to
“determine that the defendant understands” the “terms of any
plea-agreement provision waiving the right to appeal” the
defendant’s sentence.

     Suppose that a defendant agrees to plead guilty and signs
a written plea agreement that waives the right to appeal the
sentence. But then the district court, in violation of Rule 11,
fails to discuss the appeal waiver at the plea hearing. On
appeal, do we still enforce the appeal waiver?

     This Court has not yet decided how a district court’s
failure to comply with Rule 11(b)(1)(N) affects the validity of
an appeal waiver. The text of Rule 11(h) guides our analysis.
Rule 11(h) provides that a Rule 11 error must be deemed
harmless if the error did not affect the defendant’s “substantial
rights.” A Rule 11(b)(1)(N) error at the plea hearing does not
affect the defendant’s substantial rights if the defendant still
knowingly, intelligently, and voluntarily waived the right to
appeal. To determine whether the defendant knowingly,
intelligently, and voluntarily waived the right to appeal, the
court of appeals must examine the entire record, including both
the written plea agreement and the plea hearing.

    In this case, defendant John Han Lee entered into a written
plea agreement with the Government. In the plea agreement,
Lee waived his right to appeal a sentence that was within or
                               3
below the applicable Guidelines range. At Lee’s subsequent
plea hearing, the District Court did not discuss the appeal
waiver. Lee pled guilty and was later sentenced to a within-
Guidelines sentence of 18 months in prison, to be followed by
three years of supervised release. He has appealed his
sentence.

     After examining the entire record, we conclude that Lee
knowingly, intelligently, and voluntarily waived the right to
appeal his within-Guidelines sentence. We therefore enforce
the appeal waiver and dismiss Lee’s appeal.

                               I

    In 2013, John Han Lee entered into a written plea
agreement with the Government. Under the terms of the plea
agreement, Lee agreed to plead guilty to one count of bribery
of a public official and one count of conspiracy to commit bank
fraud. The plea agreement included the following appeal
waiver:

   Your client is also aware that the parties’ calculation of the
   sentencing range under the Sentencing Guidelines is not a
   promise of the sentence to be imposed on him and is not
   binding on the Court. Knowing that, your client waives the
   right to appeal his sentence or the manner in which it was
   determined pursuant to 18 U.S.C. § 3742, except to the
   extent that (a) the Court sentences your client to a period of
   imprisonment longer than the statutory maximum, (b) the
   Court departs upward from the applicable Sentencing
   Guidelines range pursuant to the provisions of U.S.S.G.
   §§ 5K2, or (c) the Court imposes a period of incarceration
   above the guidelines range for a total offense level of 25
   based on a Criminal History Category I. . . . In agreeing to
   this waiver, your client is aware that his sentence has not
                               4
   yet been determined by the Court.             Realizing the
   uncertainty in estimating what sentence the Court will
   ultimately impose, your client knowingly and willingly
   waives his right to appeal the sentence, to the extent noted
   above, in exchange for the concessions made by this Office
   in this Plea Agreement.

    Lee signed the plea agreement. The agreement stated that
Lee had read and understood the agreement, that he had
discussed it with his counsel, and that he was entering into the
agreement “without reservation,” “voluntarily,” and of his
“own free will.” The agreement also stated that Lee was
“satisfied” with his counsel’s services. Lee’s counsel – who
was an experienced criminal defense attorney – also signed the
plea agreement, affirming that he had “fully” discussed the
agreement’s provisions with Lee. App. 35.

    Lee then pled guilty before a magistrate judge. At the plea
hearing, Lee stated that he had attended college for a few years.
The magistrate judge asked Lee to confirm that he had
“completely and thoroughly discussed” the plea with his
counsel. Lee said that he had. Lee also said that he was
satisfied with his counsel’s services. Lee confirmed that he had
read the written plea agreement “very carefully” and that his
signature indicated his acceptance of the agreement’s terms.
Finally, the magistrate judge asked Lee if he had any questions
about the plea agreement. Lee said that he did not. App. 39-
42.

   The magistrate judge did not question Lee about the appeal-
waiver provision and, indeed, never mentioned the appeal-
waiver provision. Lee’s counsel did not object to the
magistrate judge’s failure to discuss the appeal-waiver
provision.
                               5
    At the end of the plea hearing, the magistrate judge
determined that Lee was pleading guilty knowingly and
voluntarily. The magistrate judge therefore recommended that
the District Court accept Lee’s plea. The District Court in turn
accepted the plea.

   The District Court later sentenced Lee to a within-
Guidelines sentence of 18 months of imprisonment and three
years of supervised release.

    Lee has appealed his sentence, asking us to vacate most of
the conditions of supervised release. Because we conclude that
Lee waived his right to appeal his sentence, we dismiss the
appeal.

                               II

     We must decide whether to enforce the appeal waiver
contained in Lee’s written plea agreement. We have held that
a “waiver of the right to appeal a sentence is presumptively
valid and is enforceable if the defendant’s decision to waive is
knowing, intelligent, and voluntary.” In re Sealed Case, 702
F.3d 59, 63 (D.C. Cir. 2012). An appeal waiver is knowing,
intelligent, and voluntary if the defendant “is aware of and
understands the risks involved” in waiving the right to appeal.
United States v. Guillen, 561 F.3d 527, 529 (D.C. Cir. 2009).

     To help ensure that a defendant’s appeal waiver is
knowing, intelligent, and voluntary, Rule 11(b)(1)(N) of the
Federal Rules of Criminal Procedure requires the district court,
at the plea hearing, to “inform the defendant of, and determine
that the defendant understands, . . . the terms of any plea-
agreement provision waiving the right to appeal” the
defendant’s sentence.
                                6
     Here, Lee signed a written plea agreement with the
Government in which he waived his right to appeal a within-
or below-Guidelines sentence. At the plea hearing, however,
the magistrate judge failed to discuss the appeal waiver. That
was error under Rule 11(b)(1)(N). The question is: What are
the consequences of that error?

     One might argue that a court of appeals should
automatically deem an appeal waiver not knowing, intelligent,
and voluntary if the district court failed to discuss the appeal
waiver at the defendant’s plea hearing. But no court of appeals
has adopted that automatic approach. That is not a surprise,
because the problem with such an approach is evident. When
the defendant knowingly, intelligently, and voluntarily waives
the right to appeal, it makes little sense to deem the appeal
waiver not knowing, intelligent, and voluntary merely because
it was not mentioned at the plea hearing. Moreover, such an
automatic approach would grant a windfall to the defendant. In
a plea agreement, the defendant obtains certain benefits, and
the Government obtains certain benefits. One of the benefits
the Government sometimes bargains for is the defendant’s
waiver of the right to appeal the sentence. When the defendant
knowingly, intelligently, and voluntarily waives the right to
appeal but later can still appeal because of a technical violation
at the plea hearing, the Government loses that benefit, and the
defendant obtains a windfall.

     Rule 11 deals with those concerns. In particular, Rule
11(h) provides that a district court’s error in the Rule 11 plea
colloquy must be deemed harmless if the error did not affect
the defendant’s “substantial rights.” Fed. R. Crim. P. 11(h).
Rule 11(h) thereby helps ensure that “ceremony” is not
“exalted over substance.” Id., Advisory Committee Notes to
1983 Amendments.
                                  7
     As applied to appeal waivers, Rule 11(h)’s harmless error
rule raises the following question: When does a district court’s
error in failing to discuss an appeal waiver during a plea
hearing affect a defendant’s “substantial rights”? The answer
is straightforward: The district court’s error – failure to
mention the appeal waiver at the plea hearing – cannot possibly
be said to have affected the defendant’s substantial rights if the
defendant still knowingly, intelligently, and voluntarily waived
the right to appeal. Conversely, a defendant’s substantial rights
are affected by a district court’s failure to discuss the appeal
waiver at the plea hearing if the defendant did not knowingly,
intelligently, and voluntarily waive the right to appeal. 1

     To determine whether the defendant knowingly,
intelligently, and voluntarily waived the right to appeal, the
court of appeals must analyze the entire record. See United
States v. Laslie, 716 F.3d 612, 616 (D.C. Cir. 2013) (appeals
court examines entire record to determine whether an appeal
waiver is knowing, intelligent, and voluntary); cf. United States
v. Vonn, 535 U.S. 55, 59 (2002) (appeals court may consult
entire record when considering effect of Rule 11 error on
substantial rights). A written plea agreement in which the
defendant waives the right to appeal is strong evidence that the
defendant knowingly, intelligently, and voluntarily waived the
right to appeal. Of course, a written plea agreement on its own
does not end the inquiry. Rather, the court of appeals must

     1
       Apart from those circumstances, we also will not enforce an
appeal waiver if (1) “the defendant makes a colorable claim he
received ineffective assistance of counsel in agreeing to the waiver,”
(2) “the sentencing court’s failure in some material way to follow a
prescribed sentencing procedure results in a miscarriage of justice,”
or (3) the sentencing court rests the sentence on “a constitutionally
impermissible factor, such as the defendant’s race or religion.”
United States v. Guillen, 561 F.3d 527, 530-31 (D.C. Cir. 2009). Lee
does not invoke any of those three exceptions to enforcement here.
                                  8
examine, among other things, the clarity of the written plea
agreement, the defendant’s signature on the agreement, defense
counsel’s signature on the agreement, the defendant’s
statements at the plea hearing, defense counsel’s statements at
the plea hearing, and the judge’s questioning and statements at
the plea hearing. 2

                                 III

    In the District Court, Lee did not object to the Rule
11(b)(1)(N) error that occurred at his plea hearing. As a result,

     2
       If an appeal waiver is not knowing, intelligent, and voluntary,
then a court of appeals has to decide whether the proper remedy is to
void the appeal waiver while maintaining the guilty plea, to allow the
defendant to withdraw the guilty plea, to give the defendant a choice
between those two remedies, or to do something else altogether. This
Court has previously voided an invalid appeal waiver while allowing
the defendant to preserve his guilty plea. See, e.g., United States v.
Hunt, 843 F.3d 1022 (D.C. Cir. 2016); United States v. Kaufman, 791
F.3d 86 (D.C. Cir. 2015); United States v. Fareri, 712 F.3d 593 (D.C.
Cir. 2013); United States v. Godoy, 706 F.3d 493 (D.C. Cir. 2013).
Other federal courts of appeals vary in their approaches to the
remedy. See, e.g., United States v. Borrero-Acevedo, 533 F.3d 11,
16-19 (1st Cir. 2008); Tellado v. United States, 745 F.3d 48, 53-55
(2d Cir. 2014); United States v. Goodson, 544 F.3d 529, 539-41 (3d
Cir. 2008); United States v. Manigan, 592 F.3d 621, 627-28 (4th Cir.
2010); United States v. Oliver, 630 F.3d 397, 411-12 (5th Cir. 2011);
United States v. Murdock, 398 F.3d 491, 496-98 (6th Cir. 2005);
United States v. Sura, 511 F.3d 654, 658-62 (7th Cir. 2007); United
States v. Frook, 616 F.3d 773, 777 (8th Cir. 2010); United States v.
Arellano-Gallegos, 387 F.3d 794, 796-97 (9th Cir. 2004); United
States v. Edgar, 348 F.3d 867, 870-73 (10th Cir. 2003). The
Supreme Court has not addressed the proper remedy for an invalid
appeal waiver. Cf. United States v. Dominguez Benitez, 542 U.S. 74
(2004) (addressing what a defendant needs to show in order to
reverse his conviction due to a Rule 11 error at the plea hearing).
                                   9
he has the burden to show that the error affected his substantial
rights. He must demonstrate that he did not knowingly,
intelligently, and voluntarily waive his right to appeal. Lee has
not made that showing. 3

     To begin with, the language of the appeal-waiver provision
in the written plea agreement was crystal clear. Lee signed the
agreement. The agreement stated that Lee had read and “fully”
understood the agreement, had discussed it with his counsel,
and was entering into the agreement voluntarily.

     During the plea process, Lee’s counsel was an experienced
criminal defense attorney. Lee’s counsel also signed the plea
agreement and affirmed that he and Lee had “fully” discussed
the agreement’s provisions. As the Federal Public Defender
stated at oral argument in our Court, moreover, it is standard
practice for criminal defense attorneys to discuss appeal
waivers with their clients when considering plea agreements.
See Tr. of Oral Arg. at 38:19-39:1 (Court: “Wouldn’t Counsel
ordinarily discuss the appeal waiver with a Defendant who’s
signing an agreement?” Mr. Kramer: “I have to say yes,
because of course a lawyer is supposed to do that. . . . In how
much detail, varies immensely amongst counsel.”).

    At the plea hearing, Lee orally reaffirmed to the Court that
he had read the plea agreement “very carefully,” had
“completely and thoroughly discussed” the plea deal with his
counsel, and did not have any questions about the plea

     3
       Where, as here, a defendant fails to object to a Rule 11
violation in the district court, our review is for plain error, with the
burden on the defendant to show that the error affected his substantial
rights. If the error had been preserved in the District Court, our
review would be for harmless error, with the burden on the
Government to show that the error did not affect substantial rights.
See United States v. Vonn, 535 U.S. 55, 58-59 (2002).
                              10
agreement. Lee stated, in addition, that he was satisfied with
his counsel.

     On the other side of the ledger, we find no record evidence
suggesting that Lee was confused or somehow misunderstood
the appeal-waiver provision of the plea agreement during the
plea process.

     Lee suggests that the District Court muddied Lee’s
understanding of the appeal-waiver provision when the court
made an overbroad statement at the later sentencing hearing
that Lee had a right to appeal his sentence. In so arguing, Lee
points to cases where we have declined to enforce an otherwise
unambiguous appeal waiver because the district court
mischaracterized the waiver at the plea hearing. See, e.g.,
United States v. Kaufman, 791 F.3d 86, 88 (D.C. Cir. 2015);
United States v. Godoy, 706 F.3d 493, 495-96 (D.C. Cir. 2013).
But Lee’s case is different, because “a statement made at the
sentencing hearing,” even if it was misleading, “could not have
informed (or misinformed)” his decision to waive his right to
appeal, which “was made at the earlier plea hearing.” United
States v. Guillen, 561 F.3d 527, 531 (D.C. Cir. 2009) (emphasis
added); see United States v. Cook, 722 F.3d 477, 482 (2d Cir.
2013).

     In short, we conclude that Lee knowingly, intelligently,
and voluntarily waived his right to appeal his sentence. The
District Court’s Rule 11(b)(1)(N) error at the plea hearing
therefore did not affect Lee’s substantial rights. In so ruling,
we emphasize that Rule 11(h)’s harmless error rule “should not
be read as an invitation to trial judges to take a more casual
approach to Rule 11 proceedings. . . . Subdivision (h) makes no
change in the responsibilities of the judge at Rule 11
proceedings, but instead merely rejects the extreme sanction of
                            11
automatic reversal.” Fed. R. Crim. P. 11(h), Advisory
Committee Notes to 1983 Amendments.

                           ***

    We conclude that Lee knowingly, intelligently, and
voluntarily waived the right to appeal his within-Guidelines
sentence. We therefore dismiss Lee’s appeal.

                                                So ordered.
       ROGERS, Circuit Judge, dissenting: Federal Rule of
Criminal Procedure 11 is a “guilty-plea safeguard[]” for the
right to appeal, United States v. Ruiz, 536 U.S. 622, 631 (2002),
a right “fundamental to the protection of life and liberty and
therefore a necessary ingredient of due process of law,” Griffin
v. Illinois, 351 U.S. 12, 20 (1956) (Frankfurter, J., concurring).
Among the rights of which the district court “must inform the
defendant” prior to accepting a guilty plea is “the terms of any
plea-agreement provision waiving the right to appeal or to
collaterally attack the sentence.” FED. R. CRIM. P. 11(b)(1)(N)
(enacted as Rule 11(c)(6), effective Dec. 1, 1999). The district
court also “must . . . determine that the defendant understands
. . . the terms of” this waiver. Id.

     Rule 11 was amended to include the right to appeal “to
reflect the increasing practice of including provisions in plea
agreements which require the defendant to waive certain
appellate rights.” FED. R. CRIM. P. 11, Advisory Committee
Notes to 1999 Amendments; see United States v. Sura, 511
F.3d 654, 658 (7th Cir. 2007). “[T]he [Advisory] Committee
believed it was important to insure that first, a complete record
exists regarding any waiver provisions, and second, that the
waiver was voluntarily and knowingly made by the defendant.”
Committee Notes to 1999 Amendments. A Rule 11(b)(1)(N)
inquiry is thus of critical importance in ensuring that “[a]n
anticipatory waiver — that is, one made before the defendant
knows what the sentence will be — is nonetheless a knowing
waiver [because] the defendant is aware of and understands the
risks involved in his decision.” United States v. Guillen, 561
F.3d 527, 529 (D.C. Cir. 2009); see United States v. Arellano-
Gallegos, 387 F.3d 794, 797 (9th Cir. 2004).

    Here, the Magistrate Judge who accepted Lee’s guilty plea
pursuant to a plea agreement, and the district court judge who,
by minute order, adopted the Magistrate Judge’s
recommendation to accept the plea, never informed Lee that he
was waiving his right to appeal and to collaterally attack his
                               2
sentence. Lee now seeks to challenge certain supervised
release conditions in the written judgment of conviction, and
the government maintains that his challenge is barred by the
appeal waiver in his plea agreement.

     The harmless error provision of Rule 11, which, excuses
error “not affect[ing] substantial rights,” FED. R. CRIM. P.
11(h), was added as a narrow exception aimed at “end[ing] the
practice . . . of reversing automatically for any Rule 11 error,”
United States v. Vonn, 535 U.S. 55, 66 (2002); see FED. R.
CRIM. P. 11(h), Advisory Committee Notes to 1983
Amendments. Where, as here, no objection was made to a
failure under Rule 11(b)(1)(N), the defendant must show that
the error was plain and affected his substantial rights. Vonn,
535 U.S. at 63 (citing United States v. Olano, 507 U.S. 725,
736 (1993)). Therefore, the threshold question is whether Lee
has demonstrated the failure to inform him as required by Rule
11(b)(1)(N) was error that was plain and affected his
substantial rights.

     Lee has shown there was error, for the plain text of Rule
11(b)(1)(N) imposes a mandatory requirement on the district
court. During the plea colloquy, no mention was made of the
plea agreement provision waiving Lee’s right to appeal by the
Magistrate Judge, or even by the prosecutor or defense counsel.
Nor did the Magistrate Judge expressly determine that Lee
understood the terms of the waiver provision. Lee has also
shown that the error was plain. See United States v. Shemirani,
802 F.3d 1, 3 (D.C. Cir. 2015); Guillen, 561 F.3d at 531; United
States v. Murdock, 398 F.3d 491, 497 (6th Cir. 2005); Arellano,
387 F.3d at 796. What happened in Lee’s case was a
“‘wholesale’” violation of Rule 11(b)(1)(N), Murdock, 398
F.3d at 497 (quoting Arellano, 387 F.3d at 797), not merely a
technical violation as might fall within the narrow scope of
Rule 11(h). So the question is whether Lee has shown that his
                                3
substantial rights were affected, and if so, whether the error
“seriously affect[ed] the fairness, integrity or public reputation
of judicial proceedings.” Olano, 507 U.S. at 732 (internal
quotation marks and citation omitted). For the following
reasons I conclude that there was plain error as to the appeal
waiver, and upon reaching the merits of his appeal I conclude
that Lee’s case must be remanded with regard to the “standard”
conditions of his supervised release.

                                I.

     The Supreme Court has instructed that in seeking reversal
of a conviction after a guilty plea on the ground of plain error
under Rule 11, the defendant “must show a reasonable
probability that, but for the error, he would not have entered the
plea.” United States v. Dominguez Benitez, 542 U.S. 74, 83
(2004). Lee does not seek reversal of his conviction but merely
to void the appellate waiver provision in order to challenge
conditions of his supervised release. This court has yet to apply
Dominguez Benitez in that context, and the circuit courts of
appeal have taken different approaches. See Shemirani, 802
F.3d at 3 (collecting cases). For instance, the Third Circuit has
held that where

       the defendant does not seek the reversal of his
       conviction (i.e., does not seek to withdraw his guilty
       plea) but only challenges the validity of his appellate
       waiver so that he may appeal from his sentence, he is
       obliged to show a reasonable probability that the Rule
       11 error precluded him from understanding that he had
       a right to appeal and that he had substantially agreed to
       give up that right.

United States v. Corso, 549 F.3d 921, 929 (3d Cir. 2008)
(internal quotation marks and citation omitted) (emphasis
                               4
added). Other circuits take the same or a similar approach. See
e.g., Murdock, 398 F.3d at 496; Arellano, 387 F.3d at 797; see
also United States v. Burden, 860 F.3d 45, 53–54 (2d Cir.
2017). Still other circuits have held that a defendant
challenging a Rule 11(b)(1)(N) error who is not seeking
reversal of his conviction must still show that he would not
have otherwise entered the plea. See United States v. Tanner,
721 F.3d 1231, 1236 (10th Cir. 2013); United States v. Polak,
573 F.3d 428, 431 (7th Cir. 2009); United States v. Borrero-
Acevedo, 533 F.3d 11, 16–18 (1st Cir. 2008).

     Interpreting the substantial prejudice standard to
emphasize the defendant’s understanding of his waiver, as in
Corso, Murdock, and Arellano, accords with this court’s
precedent that the record must show a defendant “knows what
he is doing” in waiving the right to appeal. Guillen, 561 F.3d
at 530 (internal quotation marks and citation omitted). Under
this approach, a defendant’s substantial rights were affected if
“there was no functional substitute” for a Rule 11(b)(1)(N)
inquiry. Murdock, 398 F.3d at 497; see Corso, 549 F.3d at 931;
Arellano, 387 F.3d at 797. Even courts requiring a defendant
to show he would not have entered his plea have held that “[i]f
the safeguard required by Rule 11 is missing, the record must
reveal an adequate substitute for it.” Sura, 511 F.3d at 662. A
review of the district court record in Lee’s case, see Vonn, 535
U.S. at 74–76, reveals the “absence of any indication on the
record that the defendant understood that he had a right to
appeal and that he was giving up that right,” Murdock, 398 F.3d
at 497 (citing Arellanos, 387 F.3d at 797).

     This court in Guillen, while agreeing with our sister
circuits that waivers of the right of appeal “generally may be
enforced,” 561 F.3d at 529, and “[d]rawing upon the
experience of sister circuits,” identified “some circumstances
that may lead a reviewing court not to enforce a pre-sentence
                                5
waiver,” id. at 530 (citing decisions from the First, Fourth,
Eighth, and Tenth Circuits). For instance, the court explained:

         Nor should a waiver be enforced if the sentencing
         court’s failure in some material way to follow a
         prescribed sentencing procedure results in a
         miscarriage of justice. If, for example, the district
         court utterly fails to advert to the factors in 18 U.S.C.
         § 3553(a), then this court may disregard the waiver
         and consider the defendant’s argument that the district
         court imposed an unlawful sentence.

Id. at 531 (emphasis added). More recently, the court observed
that “[i]n order to assure consistent enforceability of waivers of
rights in plea agreements, courts conducting plea colloquies
must scrupulously adhere to the obligations of Rule 11.”
Shemirani, 802 F.3d at 3. That did not happen in Lee’s case.

     The court’s analysis today focuses on factors other than
Lee’s understanding of the terms of his waiver of the right to
appeal. Although the court acknowledges that a plea
agreement itself does not dispose of the inquiry of whether
Lee’s substantial rights were affected, see Op. 7, it nonetheless
points to the “clarity of the written plea agreement” along with
Lee’s and his counsel’s signatures on the agreement as
additional evidence of the knowing, intelligent, and voluntary
nature of the plea, id. at 7–8. But these details are all elements
of the written plea agreement, and “‘[t]he point of Rule
11(b)(1)(N) is that a signed piece of paper is not enough.’”
Corso, 549 F.3d at 930 (quoting Sura, 511 F.3d at 662)
(alteration in original).

    The court also overstates the role of Lee’s “experienced”
defense counsel. Op. at 4. The text of Rule 11(b)(1), that “the
court must inform the defendant” of the listed information, is
                                6
mandatory. “A judge is not relieved of the duty to make the
full inquiry required by Rule 11 merely because defense
counsel is present at the plea hearing . . . .” 1A Charles Alan
Wright & Andrew D. Leipold, FEDERAL PRACTICE AND
PROCEDURE: CRIMINAL § 176, at 200 (4th ed. 2008). Similarly,
the court overstates the significance of the response by Lee’s
appellate counsel to its own question about what defense
counsel “ordinarily” advise their clients, Tr. of Oral Arg. at 38
lines 18–25 through 39 lines 1–4 (Jan. 18, 2018), which was
not an observation about what transpired in Lee’s case. See
Op. 9. The Magistrate Judge’s inquiries to Lee whether he had
any questions, see Plea Hr’g Tr. at 4 lines 17–24; 6 lines 24–25
through 7 line 1, effectively shifted to Lee and his counsel the
responsibility that Rule 11(b)(1)(N) places on the district court.

     Further, although Lee responded affirmatively when asked
by the Magistrate Judge whether he understood the plea
agreement, see Plea Hr’g Tr. at 6 lines 11–13, no specific
mention was ever made of the waiver of the right to appeal.
Instead, the Magistrate Judge advised Lee of some of the rights
that he would be waiving by not going to trial — including the
right to claim ineffective assistance of counsel, present witness
testimony and cross-examine the government’s witnesses, and
require the trier of fact to find the government had proven his
guilt beyond a reasonable doubt, id. at 3 lines 19 through 4 line
1 — but “confusingly omitted the right to appeal,” Sura, 511
F.3d at 662.

    In sum, neither the written plea agreement nor defense
counsel’s statement that he had discussed the plea agreement
with Lee, nor anything else in the district court record reveals
“any indication” specifically that Lee “understood that he had
a right to appeal and that he was giving up that right.”
Murdock, 398 F.3d at 497. Indeed, although not dispositive,
see Guillen, 561 F.3d at 531, at his sentencing, the district court
                               7
judge told Lee that he had the right to appeal his sentence,
referred to the date when an appeal had to be filed, and
confirmed that Lee understood he had this right. Sentencing
Hr’g Tr. at 56:17–23. Neither the prosecutor nor defense
counsel attempted to correct the judge’s statement, see United
States v. Kaufman, 791 F.3d 86, 88 (D.C. Cir. 2015); United
States v. Godoy, 706 F.3d 493, 495–96 (D.C. Cir. 2013),
underscoring perhaps the absence of any specific indication
that an express determination had been made that Lee had
knowingly and voluntarily waived his right to appeal his
sentence.

     In thereby showing that his substantial rights were
affected, Lee has also shown that the error seriously affected
the fairness, integrity, and public reputation of our plea
proceedings. The district court’s “‘wholesale failure’ to
ascertain that [Lee] understood the waiver provision,”
Murdock, 398 F.3d at 498 (quoting Arellano, 387 F.3d at 797),
cast aside the safeguard in Rule 11(b)(1)(N) and substituted no
other. The error is exacerbated by the government’s effort to
enforce the waiver even though it failed to object to the
Magistrate Judge’s omission, see id. at 498–99, and to the
sentencing judge’s statement that Lee could appeal his
sentence, see also Guillen, 561 F.3d at 530–31. Consequently,
the appeal-waiver provision in the plea agreement does not bar
Lee’s appeal of conditions of his supervised release in the
written judgment of conviction.

                              II.

    It is long settled that the oral sentence announced at the
sentencing hearing is controlling. See United States v. Jackson,
848 F.3d 460, 465–66 (D.C. Cir. 2017); Kennedy v. Reid, 249
F.2d 492, 495 (D.C. Cir. 1957); United States v. McMillian,
777 F.3d 444, 451 (7th Cir. 2015); FED. R. CRIM. P. 35(c)
                                8
(defining “sentencing” as “the oral announcement of the
sentence”). A written judgment may clarify an oral sentence,
but “‘the written judgment form is a nullity to the extent it
conflicts with the previously pronounced sentence.’” United
States v. Love, 593 F.3d 1, 9 (D.C. Cir. 2010) (quoting United
States v. Booker, 436 F.3d 238, 245 (D.C. Cir. 2006)). Thus,
“[w]hen the two are in conflict, we will order the judgment
corrected to conform to the sentence imposed from the bench.”
Id. (citing United States v. Lewis, 626 F.2d 940, 953 (D.C. Cir.
1980)).

      Lee contends broadly that his case should be remanded to
the district court to delete the supervised release conditions that
were never mentioned at oral sentencing because the district
court judge’s statement that he “will impose standard
conditions of supervised release” was “insufficient to
constitute an oral pronouncement of any particular condition.”
Appellant’s Br. 12. Alternatively, he contends that even if the
court does not vacate the 13 “standard” conditions, ten of the
13 “standard” conditions are invalid because they are vague or
otherwise invalid for lack of notice or justification. 1 As to his
first contention, Lee relies on Love, 593 F.3d at 11. In Love,
this court recognized that “[o]ral pronouncements of
supervised release conditions are often worded imprecisely”
and emphasized the necessity of considering context when
determining whether a written judgment is consistent with an

    1
      See generally Appellant’s Br. 16–20 (citing United States
v. Kappes, 782 F.3d 828, 835–36, 842–48 (7th Cir. 2015);
United States v. Thompson, 777 F.3d 368, 372–73, 378–79 (7th
Cir. 2015) (citing, inter alia, Christine S. Scott-Hayward,
Shadow Sentencing: The Imposition of Federal Supervised
Release, 18 BERKELEY J. CRIM. L. 180 (2013))).
                               9
oral sentence. See id. at 10. There, the court concluded some
of the conditions in the written judgment were consistent with
the oral sentence, but ordered vacatur of a condition in the
written judgment that conflicted with the oral sentence,
because it prohibited the defendant from possessing
pornography while the more limited condition announced at
“sentencing” prohibited patronizing places where pornography
could be accessed. Id. at 10–11. Even assuming Lee’s
interpretation of Love — that a mere difference between a
written judgment and oral sentence warrants remand — may be
overbroad, his challenge to the supervised release conditions
embraces the narrower principle in Love that a conflict between
a written judgment and oral sentence warrants remand.

     Lee contests application of the plain error standard, as the
government urges, on the ground that he had no opportunity to
object to conditions in the written judgment because he had no
knowledge at oral sentencing of the challenged conditions. The
Sentencing Guidelines separately identify the “mandatory,”
“standard,” and “special” conditions for supervised release and
refer generally to other conditions that may be imposed, subject
to two limitations, U.S.S.G. § 5D1.3 (2015 & 2016); defense
counsel is presumed to be familiar with the Guidelines, United
States v. Abney, 812 F.3d 1079, 1089–90 (D.C. Cir. 2016). If
there were any confusion or ambiguity, Lee offers no reason
why clarification could not have been sought from the
sentencing judge on the specific supervised release conditions
being imposed. See United States v. Mack, 841 F.3d 514, 518,
526 (D.C. Cir. 2016). Even if Lee has the burden of showing
plain error, however, this court has acknowledged that his
burden to show prejudice is “somewhat lighter in the
sentencing context,” requiring only “a reasonable likelihood
that the sentencing court’s obvious errors affected his
sentence.” United States v. Saro, 24 F.3d 283, 288 (D.C. Cir.
1994). This is because the interest in finality is of a lesser
                               10
order, given that resentencing is “nowhere near as costly or as
chancy an event as a trial.” Id. at 287–88.

     The record shows Lee was substantially prejudiced as a
result of the lack of specificity at oral sentencing regarding the
“standard” conditions. As the government notes, Appellee’s
Br. 23 n.3, the 2015 Guidelines were amended prior to Lee’s
sentencing. Although his plea was entered in 2014, Lee was
sentenced on April 26, 2017; the amended Guidelines took
effect November 1, 2016. Yet the written judgment of May 8,
2017, imposes the “standard” conditions in the 2015 version of
the Guidelines when the Guidelines required that the 2016
version, which was in effect at the time Lee was sentenced, be
applied. U.S.S.G § 1B1.11(a) (2015 & 2016); see United
States v. Haipe, 769 F.3d 1189, 1191 (D.C. Cir. 2014).
Inclusion of the 2015 Guidelines’ supervisory release
conditions in the written judgment was error, and the
contextual approach applied in Love, 593 F.3d at 10, does not
resolve Lee’s challenge because there is a conflict between the
written judgment and the oral sentence. The district court
judge is presumed to have referred to the correct, 2016
Guidelines, see, e.g., United States v. Kenny, 846 F.3d 373, 376
(D.C. Cir. 2017), but this version is not reflected in the written
judgment. The significance of this conflict is manifest from the
discrepancies between the 2015 and 2016 Sentencing
Guidelines because the “standard” conditions in the 2016
Guidelines address Lee’s vagueness objections to some of the
conditions in the written judgment. For example, the 2016
version defines the term “judicial district” to mean the place
where the defendant resides while the 2015 Guidelines were
unclear, Lee notes, whether the term referred only to the
District of Columbia where he entered the plea and was
sentenced and not Virginia where he resides. Compare
U.S.S.G. § 5D1.3(c)(3) (2016) with id. § 5D1.3(c)(1) (2015).
Additionally, the 2016 Guidelines, unlike the 2015 Guidelines,
                              11
define what it means to “work regularly.” Compare id.
§ 5D1.3(c)(7) (2016) with id. § 5D1.3(c)(5) (2015). The 2016
Guidelines also omit certain “standard” conditions to which
Lee also objects, for instance to requirements that he not
frequent places where controlled substances are used,
distributed, or administered, and not consume excessive
alcohol. Compare id. § 5D1.3(c)(7) & (8) (2015) with id.
§ 5D1.3(c) (2016).

     Because the written judgement subjects Lee to “standard”
conditions that have either been clarified or omitted from the
2016 Guidelines, which should have been applied, a remand is
required. Lee’s challenge to two “special” financial conditions
that were not mentioned at “sentencing,” contending they must
be vacated, is unavailing. There is no difference, much less
conflict, between the 2016 and 2015 Guidelines versions of
these “special” conditions, compare U.S.S.G. § 5D1.3(d)
(2016) with id. (2015), and Lee offers no basis to conclude that
these conditions are not “reasonably related” to the crimes to
which he pleaded guilty, or involve a “greater deprivation of
liberty than is reasonably necessary,” 18 U.S.C. § 3583(d)(1)
& (2); U.S.S.G. § 5D1.3(b). Any error due to the failure to
mention these two “special” conditions at the sentencing
hearing was harmless. See United States v. Ayers, 795 F.3d
168, 172, 176 (D.C. Cir. 2015) (citing Williams v. United
States, 503 U.S. 193, 203 (1992); FED. R. CRIM P. 52(a)). In
view of my conclusion that a remand is required, I need not
further address Lee’s alternative contention on vagueness and
invalidity.

     Accordingly, I respectfully dissent because Lee’s
challenge to the supervised release conditions in the written
judgment of conviction is not barred by the appellate waiver
provision in his plea agreement, and, in view of prejudicial
legal error resulting in a conflict between the written judgment
                              12
and the oral sentencing, a remand with regard to the “standard”
conditions of his supervised release is required, see Love, 593
F.3d at 9–11.
