                 FOR PUBLICATION
 UNITED STATES COURT OF APPEALS
      FOR THE NINTH CIRCUIT

JOHNATHAN ANDREW DOODY,              
             Petitioner-Appellant,
                                           No. 06-17161
               v.
DORA B. SCHRIRO; MEGAN SAVAGE;              D.C. No.
                                         CV-98-00528-EHC
ATTORNEY GENERAL OF THE
                                            OPINION
STATE OF ARIZONA,
           Respondents-Appellees.
                                     
       Appeal from the United States District Court
                for the District of Arizona
        Earl H. Carroll, District Judge, Presiding

                 Argued and Submitted
       December 3, 2007—San Francisco, California

                Filed November 20, 2008

       Before: Betty B. Fletcher, Marsha S. Berzon,
          Johnnie B. Rawlinson, Circuit Judges.

                Opinion by Judge Berzon




                          15611
15614                  DOODY v. SCHRIRO


                          COUNSEL

Alan M. Dershowitz and Victoria B. Eiger, Dershowitz, Eiger
& Adelson, P.C., Cambridge, Massachusetts, and New York,
New York for the petitioner-appellant.

Terry Goddard, Attorney General of Arizona, Randall M.
Howe, Chief Counsel, and Joseph T. Maziarz, Assistant
Attorney General, Criminal Appeals Section, Phoenix, Ari-
zona for the respondents-appellees.


                          OPINION

BERZON, Circuit Judge:

   Seventeen-year-old Johnathan Doody was interrogated
overnight for twelve hours straight. When, after several hours,
he fell silent and refused to answer the officers’ questions, the
officers persisted, asking dozens of questions, many over and
over again, and telling him he had to answer them. The result-
ing confession was used in Arizona state court to convict him
of multiple counts of murder and robbery. He now petitions
for a writ of habeas corpus on the grounds that (1) the warn-
ings he received pursuant to Miranda v. Arizona, 384 U.S.
436 (1966), were insufficient; (2) the officers’ words and con-
                         DOODY v. SCHRIRO                15615
duct during the interrogation effectively “de-Mirandized”
him; and (3) his confession was involuntary. We affirm the
district court’s denial of the writ on Doody’s Miranda claims,
but reverse on his voluntariness claim.

                    I.    BACKGROUND

                               A.

                                1.

   On August 10, 1991, nine bodies were discovered in a Thai
Buddhist temple outside Phoenix, Arizona. The victims were
monks and other temple residents; each had been arranged
lying face-down in a circle and shot in the head. Their living
quarters had been ransacked and robbed.

   The temple murders sparked a massive investigation. A
task force of local, state, and federal law enforcement began
to pursue leads. Ballistics reports showed that one of the
weapons involved was a .22 Marlin rifle, so task force mem-
bers were on the lookout for such rifles.

   In late August, a security guard on the local Air Force base
located a .22 Marlin rifle during a consent search of a car
belonging to Rolando Caratachea, a local high school student.
Shortly afterward, task force detective Richard Sinsabaugh
followed up by asking Caratachea if he could borrow the rifle.
Although Detective Sinsabaugh wanted the rifle for ballistics
testing to determine if it was the murder weapon, he told Car-
atachea that it was suspected of being stolen. Caratachea
assured Detective Sinsabaugh the rifle was not stolen, but
agreed to let him take it. When he went to Caratachea’s apart-
ment to retrieve the rifle, Detective Sinsabaugh learned that
Caratachea shared the apartment with two roommates, one of
whom was seventeen-year-old Johnathan Doody.
15616                      DOODY v. SCHRIRO
  Doody was born in Thailand and moved to the United
States as a child with his American stepfather, who was in the
Air Force, and his Thai mother.1 He speaks English with
apparent fluency but a light accent.2 At the time of the investi-
gation, Doody was beginning his junior year in high school,
worked at the local Air Force base’s commissary, and was a
member of the junior Reserve Officers’ Training Corps
(“ROTC”).

  While Caratachea’s rifle was being tested, the task force
pursued other avenues of investigation, including interview-
ing members of the local Thai community who might have
useful information about the temple or its residents. In mid-
September, Detective Sinsabaugh interviewed Doody as part
of this effort. Doody’s brother had lived at the temple for a
while before the murders, and Doody had frequently visited
him during that period. During this interview, which lasted
about an hour, Doody talked about his brother’s experience
and Doody’s visits to the temple.

   On the same day as this interview, the task force received
a tip targeting four men from Tucson, who later became
known as the “Tucson Four,” as the perpetrators of the mur-
ders. After these men were interrogated by task force mem-
bers, some of whom also conducted Doody’s later
interrogation, all four confessed to the crimes. By early Octo-
  1
     Doody’s brief recounts additional evidence about his background pro-
duced at the sentencing hearing. Under Arizona law, however, review of
a decision on a motion to suppress is based solely on evidence before the
court at the time of the motion, State v. Spears, 908 P.2d 1062, 1069 (Ariz.
1996), and the Arizona Court of Appeals considered only such evidence.
State v. Doody, 930 P.2d 440, 445-46 n.4 (Ariz. Ct. App. 1996). Because
we hold Doody’s confession involuntary based on the evidence presented
at the suppression hearing, we need not decide whether a habeas court in
this situation could properly consider the additional evidence from the sen-
tencing hearing.
   2
     The characteristics of Doody’s speech are evident from a review of the
audio tapes in evidence.
                           DOODY v. SCHRIRO                         15617
ber, the Tucson Four had been charged with the murders, and
the task force members believed they had solved the crime.
The murder weapon, however, still had not been identified.

   Then, on October 24, a laboratory report concluded that
Caratachea’s rifle was the murder weapon. The task force
immediately decided to interview Caratachea and all of his
known friends. Because Doody and Caratachea had been
roommates, Doody was on the interview list. The following
day, when task force members interviewed Caratachea, he
told them that, just before the temple murders, he loaned his
rifle to Doody and Alessandro Garcia, a sixteen-year-old
friend of Doody and Caratachea.

                                    2.

   On the evening of Friday, October 25, 1991, while Carat-
achea’s interview was still in progress but after Caratachea
told officers he had loaned the rifle to Doody, two task force
members approached Doody at a high school football game
and asked him to come to the police station to answer ques-
tions. He agreed and was driven to the station by one of the
officers.

   At 9:25 p.m., two police officers began an interview that
did not end until 10:00 a.m. the following morning. The entire
interview was audio-taped. Doody was not informed of the
taping and was not aware of it.3 The interview took place in
a carpeted, ten-foot by eighteen-foot room furnished only
   3
     All seventeen audio tapes were part of the record below. It appears,
however, that the parties included transcripts of only nine of the tapes in
the district court record. The parties supplied this Court with the tran-
scripts of the remaining eight tapes.
   In general, appellate courts are limited to the evidentiary record pres-
ented to the lower court. FED. R. APP. P. 10(a). For that reason, and
because they are in any event more accurate, we rely on the audio tapes
rather than the written transcripts.
15618                      DOODY v. SCHRIRO
with three chairs. Doody was offered food, drink, and bath-
room breaks several times during the night, although he never
accepted food. Other than two brief bathroom breaks in the
morning hours, the interview went on continuously during the
twelve hours.

  The interrogation was initially conducted by Detectives
Riley and Munley. Detective Riley began with a casual intro-
duction:

      [S]ince we’re in kind of a formal setting and things
      like that and because [Detective Munley’s] a police
      officer and I’m a police officer and things like that,
      sometimes some of the questions that we get into
      are, are a little bit sensitive and things like that. And
      what I’d like to do is before we, we go into that is
      read something to you and, so that you understand
      some of the protections and things that, that you
      have. It’s not meant to scare you or anything like
      that. Don’t, don’t take it out of context, okay.

He asked Doody if he had heard of Miranda warnings; Doody
responded that he had not. Detective Riley repeatedly assured
Doody that the warnings were “not meant to scare you” and
told him, “I don’t want you to feel that because I’m reading
this to you that we necessarily feel that you’re responsible for
anything. It’s for your benefit, it’s for your protection and for
ours as well.”

   Although Detective Riley used a “juvenile Miranda warn-
ings” form,4 he orally expanded upon the written form. In par-
ticular, when reviewing the right to an attorney, Detective
Riley explained that a lawyer will “help you concerning the
  4
    In addition to the traditional Miranda warnings, this form also asks if
the juvenile wants a parent or guardian present during questioning and
warns that the juvenile’s case may be handled by adult, rather than juve-
nile, court.
                          DOODY v. SCHRIRO                        15619
crime or any kind of offense that we might think that you or
somebody else is involved in, if you were involved in it, okay.
Again, it [does] not necessarily mean that you are involved,
but if you were, then that’s what that would apply to, okay.”

  At the conclusion of each warning, Doody indicated that he
understood and initialed the juvenile Miranda form. Doody
agreed to speak to the officers without a parent or attorney
present, and the interrogation commenced.

   Detectives Riley and Munley began by asking Doody
casual questions about his roommates and friends, including
which of his friends and acquaintances owned guns. Doody
immediately volunteered that Caratachea owned a gun, but
denied ever having borrowed or shot it. The officers then
asked Doody about the temple murders, inquiring where he
was at the time of the murders and when he learned of them.
Doody readily answered the questions, stating that on the
night of the murders he saw a movie with a friend and then
went home. The officers then asked more questions about the
temple, the victims, and Doody’s visits to the temple before
the murders.

   After about an hour, Detective Riley stopped the question-
ing to deliver a brief lecture about how important it was for
Doody to tell them the truth, and then, pointedly, asked
Doody again if he or anyone he knew had ever borrowed Car-
atachea’s rifle. Doody answered that he had not, but that Gar-
cia might have. Detective Riley responded that “there are
some things about the gun that I, I know that you have knowl-
edge about,” and urged Doody to “be up front with me, be
honest with me.”5
  5
    As noted above, before Doody’s interrogation began, Caratachea had
told task force members that he loaned the rifle to Doody and Garcia
shortly before the murders. Although Caratachea’s interrogation continued
for several hours more, he never confessed to any involvement in the mur-
ders.
15620                  DOODY v. SCHRIRO
   Detective Riley again asked Doody about his whereabouts
on the night of the murders and whether he knew anything
about the murders other than what was in the news. Doody
denied any knowledge. Detective Riley again warned Doody
that “I want to stress with you the importance of being, being
up front and honest,” and told him that “[w]hat you’re saying
[about not borrowing Caratachea’s rifle] is not, is not true.”
In response, Doody again denied ever borrowing Caratachea’s
rifle but repeated that Garcia might have borrowed it.

   Detectives Riley and Munley both proceeded to lecture
Doody on how important it was for him to tell them the truth,
and, now becoming more specific, informed him they “kn[e]w
that you were along with at least one other person when [Car-
atachea]’s rifle was borrowed.” They then demanded that he
tell them about the borrowing of Caratachea’s rifle, using
words that went beyond urging or imploring: “[I]t’s so impor-
tant for you, for you to tell us. I mean you have to tell us. You
have to.” (Emphasis added.) Almost immediately after these
comments, at about 11:45 p.m., Doody admitted that he and
Garcia had borrowed Caratachea’s rifle, but insisted that the
incident had occurred well before the temple murders. He
later explained his earlier reluctance to admit to borrowing the
rifle: First, Detective Sinsabaugh had told Caratachea the gun
might be stolen, and Doody did not want to be associated with
stolen property; second, the officers’ pointed questions about
the gun plainly implied that it had some link to the temple
murders. Either way, Doody said, he was afraid to admit any
connection to the rifle.

   Detectives Riley and Munley launched into several more
monologues on how important it was for Doody to tell them
the truth and how they knew he was not doing so. This time,
however, they told Doody that Caratachea’s rifle was the mur-
der weapon. Doody insisted that he returned the rifle to Carat-
achea before the murders, and continued to deny involvement
in or knowledge of the murders despite the officers’ repeated
                           DOODY v. SCHRIRO                          15621
questions and insistence that he knew more than he was tell-
ing them.

  Undeterred by his denials, the officers pushed harder. For
almost an hour, from about 1:50 a.m. to 2:45 a.m., Detectives
Riley and Munley told Doody that the case was “busted wide
open,” that he had to protect himself from what others were
saying about him by telling them the truth, and that he knew
exactly what happened at the temple. In the few times Doody
spoke during this period he denied any knowledge or involve-
ment.

   At around 2:45 a.m., Detectives Riley and Munley were
joined by Detective Sinsabaugh, who had interviewed Doody
in September. For over two hours, all three officers were pres-
ent in the room.6 The officers began to barrage Doody with
questions. Doody essentially stopped responding altogether.
They asked him five times whose plan it was to go to the tem-
ple; Doody did not answer once. They asked fourteen times
whether it was Caratachea’s idea; Doody answered once —
that he did not know. They asked twenty-five times whether
Doody was at the temple; Doody did not answer once. During
this entire sequence, lasting twenty minutes, Doody answered
one out of forty-five questions. Framing the repetitious ques-
tioning were demands for answers: “You have to tell us,” the
officers told Doody, “We have to know; you have to let us
know.” And, frustrated by Doody’s silence, one officer
sharply directed him: “Answer, Jonathan, answer.”

   The officers next began asking a series of questions about
whether Doody was keeping silent because someone had
threatened him. Doody answered a few of these questions, but
fell silent again when the officers returned to asking him —
seven times without a response — whose idea it was to go to
  6
   At some point during this period, the three officers were joined by a
fourth, Captain White. It is not clear how long all four officers were pres-
ent in the interrogation room.
15622                  DOODY v. SCHRIRO
the temple. Doody remained silent this time for eight minutes,
failing to respond to thirty questions in a row. In the face of
Doody’s silence, Detective Sinsabaugh warned him, “I’m
gonna stay here until I get an answer,” and directed: “You’ve
got to answer me”; “Jon, answer me”; “Now, you — start
talking to me”; “Tell me Jon. Talk to me, Jon. Jon — no, no,
it’s not gonna — you’re not gonna cut it that way, man.
You’re gonna be a man about it. You’re gonna talk to me
Jon”; “[S]tart talking to me, Jon. Don’t sit there like that, talk
to me.” Doody only broke his silence when Detective Sinsa-
baugh asked him nine times whether he remembered Detec-
tive Sinsabaugh’s name, or recalled talking to him previously.
Many of Doody’s answers during this time are whispers,
barely audible on the tapes.

   At about 3:30 a.m., Detective Sinsabaugh asked him ten
times if he had been involved with the temple incident, direct-
ing him: “Answer me. Answer me, Jonathan. Jonathan,
answer me. Answer me. What, what’s the problem? Answer
me, Jonathan.” After Detective Sinsabaugh asked yet again if
Doody had been involved, Doody finally responded, “Yes.”
More than six hours into the interrogation, after forty-five
minutes of relentless questioning in the face of Doody’s
almost complete silence, this was the first statement Doody
made linking himself to the murders.

   For about a half hour after this one-word response, most of
the officers’ questions again went unanswered; what answers
Doody gave were largely monosyllabic. Showing increasing
impatience with his silence, Detective Sinsabaugh told him,
“if it’s gonna take you all night to tell me two little simple
things, we’re gonna have a problem.” But Doody still
remained silent when asked fourteen times whether Carat-
achea was involved. Detective Sinsabaugh’s frustration is
plain: “Say something. Say something, Jonathan. Come on,
man, this is ridiculous. Say something. What’s your name?
What’s your name, Jonathan? Jonathan, what’s your name?
What’s your last name?”
                           DOODY v. SCHRIRO                          15623
   Shortly after 4:00 a.m. — six and one-half hours after the
interrogation began, and without a single break in questioning
— Doody began to talk about the temple murders in a narra-
tive fashion. He told the officers that he, Garcia, Caratachea,
a friend of Caratachea’s named George, and one other person
went to the temple for what he thought was a plan to test the
temple’s security system. He described how the monks were
roused from their rooms and arranged in the living room; that
the rooms were ransacked and valuables placed in duffle
bags; and that, after one of the monks recognized George,
George said they should leave no witnesses. The others told
Doody to go outside to see if the temple was soundproof; he
then heard shots fired and ran back inside. At that point,
everyone fled.

   The officers were still, at that time, convinced that the Tuc-
son Four were involved, and refused to believe Doody’s
assertion that they were not, repeated in response to several
inquiries. After maintaining for almost two hours that only
five people went to the temple, that all of them were white,
and that the Tucson Four were not among them, Doody
finally agreed that about ten people were involved, that two
or three were black,7 and that he did not know whether some
of them were from Tucson or not. Throughout, Doody main-
tained that he never knew until the events unfolded that the
plan involved robbery or murder.

  The interrogation ended at about 10:00 a.m., over twelve
hours after it began. For almost nine hours, the interrogation
never paused; in the final three hours, Doody had only two
short breaks to use the restroom. By the end, he was sobbing.
  7
    Although the record does not so indicate, the officers’ pointed ques-
tions about the race of the people involved suggests that at least one of the
Tucson Four was black.
15624                    DOODY v. SCHRIRO
                                 B.

  Eventually, the Tucson Four were cleared of any wrongdo-
ing, and the state’s new theory was that Doody and Garcia
acted alone.8 The two were indicted for murder and armed
robbery and stood trial as adults.

                                 1.

   Doody moved to suppress his recorded statements, arguing
that the Miranda warnings were inadequate and that his con-
fession was involuntary. During a ten-day suppression hear-
ing, which also addressed Garcia’s motion to suppress his
own statements, several task force members testified; Doody
did not. The evidence included the audio tapes of Doody’s
confession and accompanying transcripts.

   Detective Riley testified that, during the Miranda warnings,
Doody “was very attentive” and displayed no confusion or
doubt. He testified that Doody’s demeanor changed over the
course of the interview, becoming less attentive and more
quiet, but that Doody never “display[ed] any real overt sign
of being fatigued or tired.” Detective Sinsabaugh testified
that, at the time Doody first confessed involvement in the
temple murders, he was “alert” and “sitting upright and
erect.” Detective Sinsabaugh also testified that he considered
Doody “real intelligent,” because he was working towards the
goal of becoming an Air Force pilot.

   The trial court denied Doody’s motion to suppress, finding
the Miranda warnings adequate and the confession voluntary.
  8
   Garcia, interrogated on the same night as Doody, also confessed to
involvement in the murders.
                           DOODY v. SCHRIRO                         15625
                                    2.

   The trial lasted thirty-four days. The state’s theory was that
Doody hatched a plan to rob the temple, intended to murder
the monks to conceal the robbery, and enlisted Garcia to help
him execute the scheme. Doody’s confession — that five, or
as many as ten, people were involved and that he did not
know of the planned robbery or murders — was at odds with
the state’s theory of his role.

   Nonetheless, the state played all seventeen tapes of
Doody’s interrogation for the jury and relied heavily on them,
arguing that various portions showed his guilt and the rest
were lies. The state’s star witness was Garcia, who pled guilty
prior to trial in exchange for the state’s agreement not to seek
the death penalty.9 Garcia testified that no one other than he
and Doody knew of or participated in the murders. He pro-
vided a detailed description of the events of that night.
According to Garcia, Doody initiated the plan to rob the tem-
ple to get money to buy a car. This motive testimony was bol-
stered by evidence that shortly after the murders, Doody paid
$1,000 for a car.

   Three witnesses testified that Doody told them, before the
interrogation at which he confessed, that he had committed
the temple murders. One witness testified that Doody said he
and the Tucson Four had together carried out the crime; the
witness thought Doody was joking at the time. Another wit-
ness stated that Doody said the military’s Office of Special
Investigations (“OSI”) was responsible for the temple killings,
and that Doody used to kill people “execution style” for
money. This witness also thought Doody was joking, and tes-
tified that other students at their high school — herself
  9
   At the same time, Garcia also pled guilty to an unrelated murder com-
mitted after the temple murders. Under the terms of the plea agreement,
Garcia would be sentenced for both crimes after testifying at Doody’s trial
and could receive between 25 and 271 years.
15626                         DOODY v. SCHRIRO
included — jokingly claimed responsibility for the murders.
The third witness testified that Doody told him the monks
were a national security threat, and that Doody eliminated
them for the OSI. This witness, according to another witness,
had a reputation for being gullible.

   The state also presented some evidence connecting Doody
to items stolen from the temple. Several items had been
pawned by Caratachea’s friend Angel Rowlett; Rowlett and
another friend of Caratachea’s testified, with immunity, that
they stole these items from Doody.10 Other items stolen from
the temple were recovered from Garcia’s bedroom, which he
shared with Doody at the time his room was searched.

   The defense theory was that the robbery and murders were
committed by Caratachea, Garcia and others, and that Doody
either had nothing to do with the incident or was there as an
innocent bystander, believing that they were only going to see
if they could breach the temple’s security system. Doody did
not testify at trial.

   The jury returned a verdict of guilty on all nine counts of
first-degree murder. As indicated by the special verdict form,
the jury convicted Doody on a theory of felony murder,
rejecting a theory of premeditated murder.11 Doody was also
convicted of multiple counts of armed robbery, one count of
burglary, and one count of conspiracy to commit armed rob-
  10
      Caratachea invoked his Fifth Amendment rights and did not testify at
the trial.
   11
      Under Arizona law, “[a] person commits first degree murder if:
       “1. Intending or knowing that his conduct will cause death, such
       person causes the death of another with premeditation; or
       “2. Acting either alone or with one or more persons such person
       commits or attempts to commit . . . robbery . . . and in the course
       of and in furtherance of such offense or immediate flight from
       such offense, such person or another person causes the death of
       any person.” ARIZ. REV. STAT. § 13-1105(A) (1991).
                         DOODY v. SCHRIRO                  15627
bery. The trial court sentenced Doody to nine consecutive life
terms for the murder counts and additional time for the other
counts.

                                 3.

   Doody appealed his conviction on several grounds, includ-
ing challenges to the adequacy of the Miranda warnings and
the voluntariness of the confession. The Arizona Court of
Appeals affirmed the trial court’s denial of the motion to sup-
press. State v. Doody, 930 P.2d 440 (Ariz. Ct. App. 1996).12

  The court found that the Miranda warnings were adequate:
“[T]he officers advised Doody of his Miranda rights in a clear
and understandable manner . . . . The officers read each warn-
ing from a standard juvenile form and provided additional
explanations as appropriate.”

   The court further concluded that the confession, despite the
length of the interrogation and Doody’s juvenile status, was
voluntary:

       Although the entire interrogation lasted approxi-
       mately thirteen hours, Doody admitted he had bor-
       rowed Caratachea’s rifle at the time of the temple
       murders after approximately two and one-half hours
       of questioning. Doody admitted he had participated
       in the temple robbery after approximately six and
       one-half hours of questioning, and his description of
       the events at the temple spanned nearly two hours
       ....

       Although Doody characterizes the tone of the inter-
       rogation as coercive, the audio tapes reveal a courte-
       ous, almost pleading style of questioning during
  12
   The Arizona Supreme Court denied review and the United States
Supreme Court denied certiorari.
15628                  DOODY v. SCHRIRO
    most of the interview. Each of the officers involved
    in the interrogation testified at the suppression hear-
    ing that Doody remained alert and responsive
    throughout the interrogation and did not appear over-
    tired or distraught. Our review of the audio tapes
    confirms the officers’ testimony.

The court noted also that “the officers offered Doody food
and drinks and accommodated his requests to use the rest-
room” and that Doody “specific[ally] consent[ed] to speak
with the officers without his parents.” As for the interrogation
tactics used, the court found that “although Doody did not
speak for long periods during the interrogation, he never
invoked his right to remain silent or his right to an attorney.”

  Doody subsequently filed a petition for a writ of habeas
corpus in federal court. The district court denied the writ.
Doody now appeals.

              II.   STANDARD OF REVIEW

   We review the Arizona Court of Appeals opinion as the last
reasoned state court opinion. See Ylst v. Nunnemaker, 501
U.S. 797, 803-04 (1991). Because Doody filed his federal
habeas petition after the effective date of the Anti-Terrorism
and Effective Death Penalty Act (“AEDPA”), he can prevail
only if he can show that the state court’s adjudication of his
claim:

    (1) resulted in a decision that was contrary to, or
    involved an unreasonable application of, clearly
    established Federal law, as determined by the
    Supreme Court of the United States; or

    (2) resulted in a decision that was based on an unrea-
    sonable determination of the facts in light of the evi-
    dence presented in the State court proceeding.
                       DOODY v. SCHRIRO                   15629
28 U.S.C. § 2254(d). A state court decision will be “contrary
to” federal law if it “applies a rule that contradicts governing
law set forth in [Supreme Court] cases” or “confronts a set of
facts that are materially indistinguishable from” a Supreme
Court case, yet reaches a different result. Williams v. Taylor,
529 U.S. 362, 405-06 (2000). A state court decision will
involve an “unreasonable application of” federal law only if
it is “objectively unreasonable.” Id. at 409.

   The prejudicial impact of any constitutional error is
assessed by asking whether the error “had substantial and
injurious effect or influence in determining the jury’s ver-
dict.” Brecht v. Abrahamson, 507 U.S. 619, 623 (1993) (quot-
ing Kotteakos v. United States, 328 U.S. 750, 776 (1946)); see
also Fry v. Pliler, 127 S.Ct. 2321, 2328 (2007) (holding that
the Brecht standard applies whether or not the state court rec-
ognized the error and reviewed it for harmlessness).

   We review the district court’s denial of Doody’s petition
for a writ of habeas corpus de novo. Clark v. Murphy, 331
F.3d 1062, 1067 (9th Cir. 2003).

                     III.   DISCUSSION

   Doody puts forward three reasons why his confession
should have been suppressed — two grounded in Miranda
principles, one in the voluntariness requirement.

   The first Miranda claim is that the Miranda warnings were
inadequate. Doody points to particular language the officers
used that he argues mischaracterized the nature of the right to
counsel. He further maintains that the officers purposefully —
and effectively — downplayed the significance of the warn-
ings, so that Doody would be more likely to waive his rights.
He argues that this strategy, coupled with Doody’s particular
vulnerability to it — because of his age, his inexperience with
law enforcement, and his cultural background — undermined
the ultimate goal of the warnings: to combat the “inherently
15630                  DOODY v. SCHRIRO
compelling pressures” of custodial interrogation by ensuring
that a suspect is “adequately and effectively apprised of his
rights.” Miranda, 384 U.S. at 467.

   Doody’s second Miranda claim is that even if the initial
warnings were adequate, the officers’ subsequent words and
conduct effectively “de-Mirandized” him. He argues that the
officers told him that what he said would remain between
them — “What you tell us right now is gonna stay right here”;
“Jonathan, we’re not even gonna go out and be telling every-
[one] what you’re saying. That’s not [the] way we do busi-
ness”; “Between us, was Alex with you”; “it’s between us and
you: who knew the guys in Tucson?” — and that these state-
ments contradicted and negated the earlier warning that any-
thing Doody said could and would be used against him.
Worse, he contends, were the officers’ multiple statements
like “You have to tell us,” “We have to know; you have to let
us know,” and “I’m gonna stay here until I get an answer.”
Doody regards these statements, coupled with the officers’
repeated questioning in the face of his lengthy silences, as
having effectively told him that he did not have the right to
remain silent, and that the interrogation would not end until
he confessed. Any previous understanding of his rights, he
argues, was thus negated, violating the principle of Miranda.

   Finally, Doody claims that his confession was coerced and
thus involuntary, so its admission at trial violated his Four-
teenth Amendment right to due process. See Dickerson v.
United States, 530 U.S. 428, 433-34 (2000). He points partic-
ularly to his age — seventeen and one-half years old — and
the corresponding susceptibility to pressure from authority
figures that comes with youth. The interrogation lasted over
twelve hours, through an entire night, without food or signifi-
cant breaks. He had never been arrested or interrogated as a
suspect before that night. His parents were not present; in fact,
Doody maintains, the task force went to some length to ensure
their absence. Doody also challenges the state court decision
as resting on an unreasonable determination of the facts. In
                      DOODY v. SCHRIRO                   15631
particular, he argues that the court of appeals’ findings that
the interrogation involved “a courteous, almost friendly style
of questioning during most of the interview” and that Doody
remained alert and responsive throughout are objectively
unreasonable. The evidence in fact shows, he urges, that he
remained nonresponsive and silent for long stretches, while
the officers, although sometimes using a pleading or courte-
ous tone, at other times issued emphatic demands and essen-
tially told him the interrogation would continue until he
confessed.

  In short, Doody paints an overall picture of downplayed
warnings, a softly induced waiver of rights, and conduct con-
veying the message that Doody would not be left alone until
he confessed, all targeted at an unsavvy, increasingly sleep-
deprived teenager.

                              A.

   [1] This case requires us to consider the interplay between
the Miranda and voluntariness analyses, an interplay which,
on the facts before us, informs both analyses. We therefore
begin by considering that interaction, and then proceed to dis-
cuss first the Miranda issues and then the voluntariness ques-
tion.

   Although generally viewed as distinct, the two doctrines
originated from the same concerns. “Over time, our cases rec-
ognized two constitutional bases for the requirement that a
confession be voluntary to be admitted into evidence: the
Fifth Amendment right against self-incrimination and the Due
Process Clause of the Fourteenth Amendment.” Dickerson,
530 U.S. at 433. Whereas the Fifth Amendment by its text
safeguards the individual against being “compelled in any
criminal case to be a witness against himself,” U.S. CONST.,
amend. V, the due process protection stems from the principle
that “tactics for eliciting inculpatory statements must fall
within the broad constitutional boundaries imposed by the
15632                  DOODY v. SCHRIRO
Fourteenth Amendment’s guarantee of fundamental fairness,”
Miller v. Fenton, 474 U.S. 104, 110 (1985); see also id. at 109
(“[C]onfessions procured by means ‘revolting to the sense of
justice’ [can]not be used to secure a conviction” (quoting
Brown v. Mississippi, 297 U.S. 278, 286 (1936))).

   [2] The due process protection is embodied in a voluntari-
ness inquiry that asks “ ‘whether a defendant’s will was over-
borne’ ” by looking at the “ ‘totality of all the surrounding
circumstances.’ ” Dickerson, 530 U.S. at 434 (quoting Sch-
neckloth v. Bustamonte, 412 U.S. 218, 226 (1973)); see also
Schneckloth, 412 U.S. at 225-26 (“ ‘Is the confession the
product of an essentially free and unconstrained choice by its
maker? If it is, if he has willed to confess, it may be used
against him. If it is not, if his will has been overborne and his
capacity for self-determination critically impaired, the use of
his confession offends due process.’ ” (quoting Culombe v.
Connecticut, 367 U.S. 568, 602 (1961))). The assessment of
the totality of the circumstances may include consideration of
the length and location of the interrogation; evaluation of the
maturity, education, physical and mental condition of the
defendant; and determination of whether the defendant was
properly advised of his Miranda rights. Withrow v. Williams,
507 U.S. 680, 693-94 (1993). Thus, by its nature, the volun-
tariness inquiry requires a case-by-case assessment, leading
courts to grapple with the application of voluntariness princi-
ples in a variety of circumstances. See Schneckloth, 412 U.S.
at 224 (“[Confession] cases yield no talismanic definition of
‘voluntariness,’ mechanically applicable to the host of situa-
tions where the question has arisen. ‘The notion of “voluntari-
ness,’ ” Mr. Justice Frankfurter once wrote, ‘is itself an
amphibian.’ ” (quoting Culombe, 367 U.S. at 604-605)).

   Miranda considered the Supreme Court’s longstanding vol-
untariness jurisprudence in the then-new context of modern
police custodial interrogations. This context “brought with it
an increased concern about confessions obtained by coer-
cion.” Dickerson, 530 U.S. at 434-35. Drawing from police
                       DOODY v. SCHRIRO                    15633
manuals and texts used by law enforcement, Miranda
described the practices used by police officers during these
interrogations to induce a suspect to confess:

    The texts . . . stress that the major qualities an inter-
    rogator should possess are patience and persever-
    ance. One writer describes the efficacy of these
    characteristics in this manner:

    “In the preceding paragraphs emphasis has been
    placed on kindness and stratagems. The investigator
    will, however, encounter many situations where the
    sheer weight of his personality will be the deciding
    factor. Where emotional appeals and tricks are
    employed to no avail, he must rely on an oppressive
    atmosphere of dogged persistence. He must interro-
    gate steadily and without relent, leaving the subject
    no prospect of surcease. He must dominate his sub-
    ject and overwhelm him with his inexorable will to
    obtain the truth. He should interrogate for a spell of
    several hours pausing only for the subject’s necessi-
    ties in acknowledgment of the need to avoid a charge
    of duress that can be technically substantiated. In a
    serious case, the interrogation may continue for
    days, with the required intervals for food and sleep,
    but with no respite from the atmosphere of domina-
    tion. It is possible in this way to induce the subject
    to talk without resorting to duress or coercion. The
    method should be used only when the guilt of the
    subject appears highly probable.”

384 U.S. at 450-51 (quoting O’HARA, FUNDAMENTALS OF CRIM-
INAL INVESTIGATION 112 (1956)). The Court concluded: “It is
obvious that such an interrogation environment is created for
no purpose other than to subjugate the individual to the will
of his examiner. . . . An individual swept from familiar sur-
roundings into police custody, surrounded by antagonistic
forces, and subjected to the techniques of persuasion
15634                     DOODY v. SCHRIRO
described above cannot be otherwise than under compulsion
to speak.” Id. at 457, 461. As the Court later described the
holding of Miranda, premised on the quoted observations,
“[w]e concluded that the coercion inherent in custodial inter-
rogation blurs the line between voluntary and involuntary
statements.” Dickerson, 530 U.S. at 435.

   [3] The Miranda Court thus considered how to safeguard
against involuntary confessions at a time when inherent pres-
sure permeated an increasingly common investigation meth-
odology. The due process voluntariness inquiry provided a
measure of protection but required case-by-case analysis. If a
certain category of cases — those involving confessions dur-
ing custodial interrogations — shared the characteristic of
inherent pressure, a uniform check at the front end of the
interrogation — the Miranda warnings, rooted in the Fifth
Amendment privilege against compelled self-incrimination —
could be more effective and efficient than the due process
back-end check. In cases in which this procedural safeguard
was not satisfied, any statements made must be suppressed.
Miranda, 384 U.S. at 444.13 Miranda thus established an irre-
buttable “presumption of coercion” for unwarned statements
made during custodial interrogations. See Oregon v. Elstad,
470 U.S. 298, 307 (1985).

   This prophylactic requirement admittedly sweeps in non-
coerced statements, and in that respect is broader than the due
process voluntariness requirement. See Miranda, 384 U.S. at
457 (“In these cases [decided in Miranda], we might not find
the defendants’ statements to have been involuntary in tradi-
tional terms.”); see also Dickerson, 530 U.S. at 444 (reaffirm-
ing Miranda while recognizing that “[t]he disadvantage of the
Miranda rule is that statements which may be by no means
involuntary, made by a defendant who is aware of his ‘rights,’
  13
    As later cases established, statements taken in violation of a defen-
dant’s Miranda rights can still be used for impeachment purposes. Harris
v. New York, 401 U.S. 222, 226 (1971).
                           DOODY v. SCHRIRO                          15635
may nonetheless be excluded and a guilty defendant go free
as a result.”). The Supreme Court nonetheless concluded that
two aspects of the Miranda rule outweigh the concerns raised
by its overbreadth. First, it is a bright-line rule and thus easier
for law enforcement and courts to apply than the voluntari-
ness analysis. See Dickerson, 530 U.S. at 444 (noting that the
totality of the circumstances inquiry “is more difficult than
Miranda for law enforcement officers to conform to, and for
courts to apply in a consistent manner”). Second, and more
significantly for our purposes, the overbreadth was considered
by the Court to be the lesser of two evils. “In Miranda, the
Court noted that reliance on the traditional totality-of-the-
circumstances test raised a risk of overlooking an involuntary
custodial confession, a risk that the Court found unacceptably
great when the confession is offered in the case in chief to
prove guilt.” Id. at 442 (internal citations omitted).

   [4] Critically, Miranda’s overinclusiveness in suppressing
some noncoerced confessions made after inadequate warnings
does not apply equally in the other direction: Warnings and a
waiver are not dispositive of a confession’s voluntariness. See
id. at 444 (“The requirement that Miranda warnings be given
does not, of course, dispense with the voluntariness inqui-
ry.”); Berkemer v. McCarty, 468 U.S. 420, 433 n.20 (1984)
(“We do not suggest that compliance with Miranda conclu-
sively establishes the voluntariness of a subsequent confes-
sion.”).14 Moreover, when analyzing the voluntariness of a
confession following Miranda warnings, the delivered warn-
ings, even if sufficient to satisfy Miranda’s prophylactic rule,
  14
    It is rare, however, that a confession following adequate Miranda
warnings and a valid waiver will be found involuntary. See Missouri v.
Seibert, 542 U.S. 600, 608-09 (2004) (plurality opinion) (“[G]iving the
[Miranda] warnings and getting a waiver has generally produced a virtual
ticket of admissibility . . . and litigation over voluntariness tends to end
with the finding of a valid waiver.”); Berkemer, 468 U.S. at 433 n.20
(“[C]ases in which a defendant can make a colorable argument that a self
incriminating statement was ‘compelled’ despite the fact that the law
enforcement authorities adhered to the dictates of Miranda are rare.”).
15636                  DOODY v. SCHRIRO
must be examined in detail, as they are part of the circum-
stances pertinent to the voluntariness inquiry. See Schneck-
loth, 412 U.S. at 226 (listing “the lack of any advice to the
accused of his constitutional rights” as a possible factor in the
voluntariness analysis); Greenwald v. Wisconsin, 390 U.S.
519, 521 (1968) (per curiam) (considering “the lack or inade-
quacy of warnings as to constitutional rights” in voluntariness
analysis).

   In Northern Mariana Islands v. Mendiola, 976 F.2d 475
(9th Cir. 1992), overruled on other grounds by George v.
Camacho, 119 F.3d 1393 (9th Cir. 1997) (en banc), for exam-
ple, we declined to decide whether the questionable Miranda
warnings alone warranted suppression of the defendant’s sub-
sequent confession. Id. at 483. Instead, we considered the
weakness of the warnings as part of the voluntariness analy-
sis, noting that “Miranda rights were administered to Men-
diola in a manner that was confusing and affirmatively
misleading,” a fact that contributed to the finding that his con-
fession was involuntary. Id. at 485-86. Similarly, in Cooper
v. Dupnik, 963 F.2d 1220 (9th Cir. 1992) (en banc), overruled
on other grounds by Chavez v. Martinez, 538 U.S. 760
(2003), a § 1983 action, the interrogating officer

    fully advised Cooper of his Miranda rights, but
    deliberately turned the advisement into what he
    hoped Cooper would perceive as a joke. [Officer]
    Barkman’s psychological ploy was designed to make
    Cooper ignore the warnings, and begin to talk. Bark-
    man intended to undercut Cooper’s Constitutional
    right not to talk to the Task Force by complying with
    Miranda’s safeguards in form only, not in spirit or
    in substance.

Id. at 1228. In concluding that Cooper stated a cause of action
based on a coercive interrogation resulting in involuntary
statements, the court noted that “Cooper was advised improp-
erly of his Miranda rights. Police officers may not make a
                       DOODY v. SCHRIRO                    15637
mockery of our Constitutional law by turning an advisement
of rights into a persiflage.” Id. at 1248; see also Sims v. Geor-
gia, 389 U.S. 404, 406-07 (1967) (per curiam) (holding — in
a case in which evidence suggested defendant was subjected
to physical violence, had been in police custody for eight
hours without access to friends or counsel, and was of limited
education and mental capacity — that “[u]nder such circum-
stances the fact that the police may have warned petitioner of
his right not to speak is of little significance”); Fikes v. Ala-
bama, 352 U.S. 191, 193, 197 (1957) (finding confession
involuntary, and noting that the interrogating officer’s “testi-
mony that he repeatedly advised petitioner ‘that he was enti-
tled to counsel and his various rights’ must be viewed in the
light of the facts concerning petitioner’s” schizophrenia and
limited education).

  The individualized examination of Miranda warnings in a
voluntariness analysis brings us back to the underlying pur-
pose of the Miranda warnings, to mitigate the inherent pres-
sure in police interrogations:

    In order to combat these pressures [inherent in a cus-
    todial interrogation] and to permit a full opportunity
    to exercise the privilege against self-incrimination,
    the accused must be adequately and effectively
    apprised of his rights and the exercise of those rights
    must be fully honored.

Miranda, 384 U.S. at 467. The warning that a suspect has the
right to remain silent

    is an absolute prerequisite in overcoming the inher-
    ent pressures of the interrogation atmosphere. It is
    not just the subnormal or woefully ignorant who suc-
    cumb to an interrogator’s imprecations, whether
    implied or expressly stated, that the interrogation
    will continue until a confession is obtained . . . .
15638                   DOODY v. SCHRIRO
Id. at 468 (footnote omitted). The warning that anything the
suspect says can be used against him in court serves in sub-
stantial part to ensure that the suspect is aware of the serious-
ness of the situation:

    This warning is needed in order to make him aware
    not only of the privilege, but also of the conse-
    quences of forgoing it. It is only through an aware-
    ness of these consequences that there can be any
    assurance of real understanding and intelligent exer-
    cise of the privilege. Moreover, this warning may
    serve to make the individual more acutely aware that
    he is faced with a phase of the adversary system —
    that he is not in the presence of persons acting solely
    in his interest.

Id. at 469. Where the warnings, although technically accurate,
are conveyed in such a way as to undermine the suspect’s
“aware[ness] that he is faced with a phase of the adversary
system,” id., and are further weakened by “[express] impreca-
tions . . . that the interrogation will continue until a confession
is obtained,” id. at 468, those circumstances can be pertinent
in appraising the totality of the circumstances concerning the
voluntariness of any ensuing confession.

   [5] In sum, although adequate Miranda warnings provide a
measure of protection against coercion in custodial police
interrogations, the protection actually provided in any given
case depends on how effective the warnings as given and
implemented were in conveying their layered messages. In
our voluntariness analysis today, therefore, we consider the
extent to which the Miranda warnings — although, as we first
conclude, technically adequate — actually protected against a
coerced confession.
                       DOODY v. SCHRIRO                    15639
                               B.

                               1.

  As we explain below, we hold the state court’s holding that
the Miranda warnings were adequate was not an “unreason-
able application of[ ] clearly established Federal law.” 28
U.S.C. § 2254(d)(1). But we also hold that the warnings were
delivered so as to minimize their effectiveness in protecting
against an involuntary confession.

   [6] The Miranda warnings given to Doody did little actu-
ally to inform him, a seventeen-year-old who had never heard
of Miranda, of the importance of his rights. The officers
downplayed the relevance of the warnings, and their applica-
tion to the current questioning. They repeatedly told Doody
that the warnings were “not meant to scare you,” and that he
should not take them “out of context.” The context, as com-
municated by the explanations surrounding the formal warn-
ings, was that the warnings were merely a formality, and that
Doody need not actually consider what their content con-
veyed. Indeed, the officers twice told Doody that the warnings
were for their benefit in part: “[I]t’s something that’s for your
benefit, as well as for ours,” suggesting that delivering the
warnings was simply a meaningless bureaucratic step they
had to take. The officers also strongly implied that Doody was
not a suspect, further underscoring the overall message that he
need not be careful of what he said, the warnings to the con-
trary notwithstanding. Doody was told, “I don’t want you to
feel that because I’m reading this to you that we necessarily
feel that you’re responsible for anything.”

   [7] The clear message underlying these comments was that
Doody need not take the warnings seriously and should waive
his rights. Thus, although each required warning was techni-
cally delivered correctly, one of Miranda’s primary purposes
— “to make the individual more acutely aware that he is
faced with a phase of the adversary system — that he is not
15640                  DOODY v. SCHRIRO
in the presence of persons acting solely in his interest,”
Miranda, 384 U.S. at 469 — was undermined.

   The officers’ elaboration on one of the specific warnings
reinforced this general message that Doody need not take the
warnings seriously. Regarding the right to an attorney, Detec-
tive Riley hedged: “[A]n attorney is a lawyer who will speak
for you and help you concerning the crime or any kind of
offense that we might think that you or somebody else is
involved in, if you were involved in it, okay. Again, it [does]
not necessarily mean that you are involved, but if you were,
then that’s what that would apply to, okay.” In addition to
being simply confusing, this explanation could be construed
to suggest that one would only ask for an attorney if he was
guilty.

   Despite the troubling subtext present throughout the warn-
ings — that Doody should disregard the content of the warn-
ings, not take the situation seriously, and waive his rights —
we cannot conclude that the state court was objectively unrea-
sonable in finding that the warnings satisfied the procedural
requirement of Miranda. Miranda warnings need not be given
“in the exact form described in that decision,” as long as they
“reasonably ‘conve[y] to [a suspect] his rights as required by
Miranda.’ ” Duckworth v. Eagan, 492 U.S. 195, 202-03
(1989) (alterations in original) (quoting California v. Prysock,
453 U.S. 355, 361 (1981)). To be found inadequate, an
ambiguous warning must not readily permit an inference of
the appropriate warning.

   For example, in United States v. Connell, 869 F.2d 1349
(9th Cir. 1989), the defendant was given two sets of warnings
about his right to appointed counsel. He was first told, both
orally and in writing, that he had to make his “own arrange-
ments to obtain a lawyer and this will be at no expense to the
Government.” Id. at 1350. He was then orally told that “a law-
yer may be appointed to represent you,” and given written
warnings stating that, if he could not afford a lawyer, “ar-
                         DOODY v. SCHRIRO                     15641
rangements will be made for me to obtain a lawyer in accor-
dance with the law.” Id. at 1353 (emphases in original). The
court held the warnings deficient:

     The oral warning, using the word “may”, leaves the
     impression that providing an attorney, if Connell
     could not afford one, was discretionary with the gov-
     ernment, particularly in light of the previous strong
     statement that “you must make your own arrange-
     ments to obtain a lawyer and this will be at no
     expense to the government.” The written warning is
     ambiguous in that the arrangements to be made for
     an attorney, if Connell could not afford one, were to
     be “in accordance with the law.” Connell is not
     expected to know what the requirements of the law
     are. In fact, conveying to the person in custody the
     requirements of the law is the whole purpose of the
     warning. Furthermore, the combination of the two
     different warnings created additional confusion.
     Thus, Connell’s case is not analogous to those situa-
     tions where, though not made explicit, the right to
     appointed counsel before and during questioning can
     readily be inferred from the combination of other
     warnings given. Rather, the ambiguous warnings he
     was given operated to dispel such an inference.

Id. (footnote omitted); see also United States v. Perez-Lopez,
348 F.3d 839, 847-48 (9th Cir. 2003) (holding inadequate
warning that “you have the right to solicit the court for an
attorney if you have no funds,” because “[t]o be required to
‘solicit’ the court . . . implies the possibility of rejection”); cf.
United States v. Miguel, 952 F.2d 285, 288 (9th Cir. 1991)
(distinguishing Connell and holding that a single warning that
defendant “may” have appointed counsel, with no prior state-
ment that defendant had to make his own arrangements, was
an adequate Miranda warning).

  [8] Here, the officers interspersed the warnings with state-
ments downplaying their significance. But the essential rights
15642                     DOODY v. SCHRIRO
were conveyed, and, unlike in cases such as Connell and
Perez-Lopez, the oral elaborations of which Doody complains
were not affirmatively misleading. Thus, although we find it
a close question, we cannot conclude that the state court’s
decision that the warnings were adequate was “objectively
unreasonable.” Williams, 529 U.S. at 409.

   [9] This conclusion only means that Miranda’s irrebuttable
presumption of coercion may not be invoked. But the exces-
sively casual delivery of Miranda warnings to a juvenile,
seemingly designed to ensure that he would ignore the warn-
ings and waive his rights, gives little comfort that Doody
commenced the interrogation with an understanding of what
was at stake. As in Mendiola and Cooper, we consider this
factor in our determination of the voluntariness of Doody’s
confession. See also Wilson v. Lawrence County, 260 F.3d
946, 953 (8th Cir. 2001) (considering, in § 1983 case alleging
a coerced confession, the fact that officers “downplayed the
importance of those [Miranda] rights to Wilson, whom they
knew was unlikely to understand them because of his low intelli-
gence”).15

  Later statements by the officers further undercut the pur-
pose of the Miranda warnings: to ensure that a suspect fully
understands his rights and the implications of waiving them.
Specifically, the officers explicitly and implicitly told Doody
— an increasingly sleep-deprived juvenile — that he did not
have the right to remain silent.16 About five hours into the
   15
      We note that although Doody initialed a written juvenile Miranda
form that properly advised him of his rights, the record does not indicate
that Doody read the form. The audio tapes reveal no silent periods during
which Doody might have been reading, and one of the officers testified at
the suppression hearing that he “handed [Doody] the form after each
advisement, and asked if he would initial the appropriate box,” suggesting
that Doody did not have the form in front of him during most of the
advisements. Moreover, even if Doody read the form, the officers’ oral
suggestions that the warnings were simply a formality undermined the
written warnings as well as the oral ones.
   16
      Doody also argues that the officers promised him his statements
would stay “between us,” that this was an improper promise, and that it
                            DOODY v. SCHRIRO                          15643
interrogation, Doody essentially stopped answering the offi-
cers’ questions. In the face of his silence, three officers took
turns asking the same questions again and again, sometimes
dozens of times in a row, and repeatedly told Doody that he
“ha[d]” to answer their questions: “You have to tell us”; “you
have to let us know”; “if it’s gonna take you all night to tell
me two little simple things, we’re gonna have a problem”;
“Answer me, answer me Jonathan. Jonathan, answer me.
Answer me.”

  With his silence, Doody gave every appearance of trying to
exercise his right to remain silent in the precise fashion
described earlier by the officers.17 During the Miranda warn-

contradicted the Miranda warning that his statements could be used
against him. The Arizona Court of Appeals rejected this interpretation of
the officers’ statements:
    [T]he officers assured Doody that his statements would not be
    disclosed to the other suspects because the officers believed
    Doody’s fear of reprisal affected his willingness to talk. The
    detectives did not imply that the state would not prosecute Doody
    if he revealed the information or that the state would not use his
    statements against him in a subsequent prosecution.
Doody, 930 P.2d at 447. Reading the statements in context, we cannot
conclude that this assessment is unreasonable, and so do not consider these
particular statements as evidence of coercive police behavior or a factor
in the involuntariness finding.
   17
      We note that Doody does not argue, either here, in the district court,
or before the state courts, that his silence in the face of repeated question-
ing was an invocation of his right to remain silent. See United States v.
Wallace, 848 F.2d 1464, 1475 (9th Cir. 1988) (holding that a suspect did
not waive right to remain silent when she remained silent for the first ten
minutes of questioning); United States v. Branson, 756 F.2d 752, 753-54
(9th Cir. 1985) (holding that a suspect invoked his right to remain silent
when he answered some questions, then remained silent when asked
another question, where officer knew at that point that the suspect did not
want to talk to the police anymore); see also Soffar v. Cockrell, 300 F.3d
588, 603 (5th Cir. 2002) (en banc) (DeMoss, J., dissenting) (“What in the
world must an individual do to exercise his constitutional right to remain
15644                     DOODY v. SCHRIRO
ings, he was told: “You can be quiet if you, if you wish.” But
when Doody was quiet, the officers told him expressly that he
had to answer them — in other words, that he could not
remain silent. Their refusal to stop questioning him reinforced
these express statements. Indeed, Doody was explicitly told
that the interrogation would continue until he confessed: “I’m
gonna stay here until I get an answer.” As a result, the offi-
cers’ original warning informing Doody of his right to remain
silent, itself a casual and underplayed message, was negated
by their subsequent conduct, telling Doody he could not be
silent, but rather that he must answer.18

   [10] In short, although the state court’s conclusion that
there was no Miranda violation was reasonable, the safety net
that proper, serious Miranda warnings provide — that of
informing a suspect of his rights and of the gravity of the situ-
ation — was quite weak in this case, prone to give way as a
protection against an involuntary confession if conditions
were otherwise conducive to such a confession. As it turns
out, they were.

silent beyond actually, in fact, remaining silent?”). But see Evans v.
Demosthenes, 98 F.3d 1174, 1176 (9th Cir. 1996) (leaving it an open ques-
tion whether, “notwithstanding . . . Davis [v. United States, 512 U.S. 452
(1994)], a defendant who wishes to assert his right to remain silent may
do so by simply remaining silent in the face of interrogation.”). We
express no view on the matter.
  18
    We do not decide, because we need not in light of our ultimate hold-
ing, whether, under clearly established federal law, this conduct “de-
Mirandized” Doody, as he argues, by providing advice contradicting that
given during the formal warnings — namely, that he was required to
answer and could not invoke his right to remain silent. See Hart v. Attor-
ney Gen., 323 F.3d 884, 894-85 (11th Cir. 2003). We do, however, con-
sider the mandatory tone and language as part of the totality of the
circumstances voluntariness analysis.
                       DOODY v. SCHRIRO                   15645
                               2.

   We now turn to the voluntariness inquiry. At the outset, we
find it notable that the officers’ long lectures on how impor-
tant it was for Doody to tell them the truth, which included
repeated statements that they “knew” his denials of involve-
ment were not true, did not alone result in his confession. Had
Doody begun to confess shortly after those admonitions, it
might be reasonable to assume that the officers persuaded him
that confessing was in his best interests. His confession would
thus be voluntary.

   [11] But Doody did not confess to any involvement in the
temple murders until about 2:45 to 3:30 a.m., after Doody had
been interrogated for several hours already, three officers sub-
jected him to forty-five minutes of repeated, overwhelmingly
unanswered questions, interspersed with commands that
Doody “had” to answer. This timing alone strongly suggests
that his will was overcome not by the interrogating officers’
pleading imprecations noted by the state court, but by the offi-
cers’ overall, interrelated, coercive messages that they would
continue relentlessly questioning him until he told them what
they wanted to hear, and that he would eventually have to do
so. See Colorado v. Connelly, 479 U.S. 157, 167 (1986)
(holding that “coercive police activity is a necessary predicate
to” a finding that a confession was not voluntary). These mes-
sages were believable, given the officers’ extraordinary per-
sistence in the face of Doody’s silence to that point, the
number of hours the interrogation had already gone on, and
Doody’s inevitable fatigue at 2:45 to 3:30 in the morning. As
Miranda noted, “[i]t is not just the subnormal or woefully
ignorant who succumb to an interrogator’s imprecations,
whether implied or expressly stated, that the interrogation will
continue until a confession is obtained.” 384 U.S. at 468.

   A somewhat similar, but considerably less coercive, situa-
tion was presented in Woods v. Clusen, 794 F.2d 293 (7th Cir.
1986). In Woods, a sixteen-year-old, after receiving Miranda
15646                      DOODY v. SCHRIRO
warnings, was interrogated for two consecutive sessions of
about twenty minutes each. During one session, the police
officers “suggested things would ‘be better’ or ‘go easier’ ” if
Woods answered the questions. Id. at 295. At the second ses-
sion, the officers deceptively told Woods that they had found
his fingerprints on the victim’s wallet. Woods answered only
one question during these sessions, before eventually confess-
ing to the crime. Id. at 295-96 The Seventh Circuit found his
confession involuntary, noting:

       Woods’ confession ended the second interrogation
       after approximately one-half hour, yet one wonders
       how long the attempt to squeeze a confession from
       Woods could have lasted? Certainly, Woods must
       have wondered if and when the inquisition would
       ever cease.

Id. at 298 (footnote omitted); compare Fare v. Michael C.,
442 U.S. 707, 726-27 (1979) (holding the confession of a
sixteen-year-old “with considerable experience with the
police” voluntary where “[h]e was not worn down by
improper interrogation tactics or lengthy questioning or by
trickery or deceit”).

   Compounding the troubling scenario in this case is Doody’s
particular vulnerability to the officers’ tactics: his age — sev-
enteen — and the length of the interrogation, more than
twelve unbroken hours, embracing an entire night.19 The
Supreme Court has long recognized that “admissions and con-
fessions of juveniles require special caution.” In re Gault, 387
U.S. 1, 45 (1967); see also Roper v. Simmons, 543 U.S. 551,
569-70 (2005) (discussing the unique vulnerabilities of juve-
niles, citing, inter alia, Johnson v. Texas, 509 U.S. 350, 367
  19
    Although the record does not explicitly so state, Doody likely attended
school the day the interrogation began. The interrogation began on a Fri-
day, and Doody was picked up at his high school, during a football game
at which he participated as part of the junior ROTC.
                           DOODY v. SCHRIRO                          15647
(1993) and Eddings v. Oklahoma, 455 U.S. 104, 115-16
(1982)). Doody’s vulnerability because of his youth was
enhanced by the fact that he had never been arrested before
and, as he told the officers, had never heard of Miranda
rights. See United States ex rel. Lewis v. Henderson, 520 F.2d
896, 901 (2d Cir. 1975) (noting that the twenty-two-year-old
suspect had “little prior experience with police methods, thus
rendering him particularly susceptible to police pressure”).20
And numerous cases recognize the coercive potential in
unbroken hours of interrogation of a juvenile, particularly
when they take place overnight. See Haley v. Ohio, 332 U.S.
596, 600-01 (1948);21 Taylor v. Maddox, 366 F.3d 992, 1014-
16 (9th Cir. 2004); Thomas v. North Carolina, 447 F.2d 1320,
1321-22 (4th Cir. 1971); compare Bridges v. Chambers, 447
F.3d 994, 999 (7th Cir. 2006) (holding a seventeen-year-old’s
confession voluntary where he was detained overnight but
“the actual questioning . . . was relatively brief . . . [and t]here
was no evidence he was not allowed to sleep between inter-
views”).
  20
      The Arizona Court of Appeals, in applying the totality of the circum-
stances voluntariness test, did not mention Doody’s lack of experience
with law enforcement. Doody argues that the state court’s failure to con-
sider this factor, as well as its failure to consider Doody’s immaturity and
cultural background, alone render the decision “contrary to” federal law,
§ 2254(d)(1), as an improper application of the totality of the circum-
stances test. We do not so hold, see Schneckloth, 412 U.S. at 226 (listing
“[s]ome of the factors taken into account” in voluntariness inquiries, not-
ing that “none of [the Supreme Court’s prior voluntariness decisions]
turned on the presence or absence of a single controlling criterion”), but
we do consider the state court’s failure to mention the factors in conclud-
ing that the decision was an “unreasonable application of clearly estab-
lished Federal law.” § 2254(d)(1).
   21
      Pre-Miranda cases remain binding on and relevant to the voluntari-
ness inquiry. See, e.g., Arizona v. Fulminante, 499 U.S. 279, 287-88
(1991) (holding a confession involuntary, relying on, inter alia, Blackburn
v. Alabama, 361 U.S. 199 (1960); Culombe v. Connecticut, 367 U.S. 568
(1961); Reck v. Pate, 367 U.S. 433 (1961); Rogers v. Richmond, 365 U.S.
534 (1961); Payne v. Arkansas, 356 U.S. 560 (1958); and Watts v. Indi-
ana, 338 U.S. 49 (1949)).
15648                      DOODY v. SCHRIRO
   Nor was Doody interrogated in the presence of any friendly
adult. Instead, he faced interrogation, alone, by two, three,
and four officers at a time. Even though Doody agreed at the
outset to speak to the officers without his parents present, the
absence of a friendly adult is a factor in assessing the volun-
tariness of a juvenile’s confession. See Gilbert v. Merchant,
488 F.3d 780, 791 (7th Cir. 2007) (“[T]he absence or pres-
ence of a parent or other friendly adult [is an] additional fac-
tor[ ] that bear[s] on the voluntariness of the juvenile’s
confession. A juvenile’s ability to consult with a friendly
adult is relevant because, as the Supreme Court explained in
Gallegos v. Colorado[, 370 U.S. 49, 54 (1962)], a teenager
may not on his own be able to fully appreciate what is at stake
when the police seek to question him . . . .” ) (citation omit-
ted); see also Gallegos, 370 U.S. at 54 (considering the
absence of a parent or attorney in the voluntariness inquiry,
even though the juvenile was advised of the right to an attor-
ney and requested neither a parent nor an attorney).22
  22
     We note that task force officers met with Doody’s stepfather three
times after they believed Doody might be connected to the murders —
twice after they knew Doody would be brought in for questioning — and
never mentioned to him their suspicions about Doody or their plans to
question him. Most tellingly, task force members interviewed Doody’s
stepfather and brother — who had traveled from out of town at the offi-
cers’ request — about the temple the day before Doody was brought in for
questioning. Although the interviewing officers learned, in the middle of
this interview, that the murder weapon belonged to Caratachea, who they
knew was Doody’s former roommate, they did not inform Doody’s stepfa-
ther of this development or suggest that he stay in town longer than he
planned. Nor was anything mentioned to Doody’s stepfather when he
stopped by the task force headquarters just hours before Doody was
picked up for questioning and after it was determined that he would be.
Finally, a task force officer met with Doody’s stepfather to reimburse him
for travel expenses on the evening of October 25 — in other words, while
officers were picking Doody up for questioning — but again did not men-
tion that his stepson was about to be interrogated.
   We recognize that voluntariness hinges on the perception of the suspect,
so circumstances of which the suspect was unaware at the time of ques-
tioning are not relevant. See Moran v. Burbine, 475 U.S. 412, 422-23
(1986); United States v. Hankey, 203 F.3d 1160, 1174 & n.13 (9th Cir.
                          DOODY v. SCHRIRO                         15649
   Indeed, the content of Doody’s confession itself provides
strong evidence that his will was overborne. Although, early
in his confession, he insisted that the Tucson Four were not
at the temple during the robbery and murders, the officers
simply refused to accept this assertion and asked many ques-
tions about the involvement of the Tucson Four. Doody
finally responded with answers consistent with the officers’
insistence that the Tucson Four were at the temple with
Doody: he said that about ten people — not five — were
involved, two or three were black, and some of them might
have been from Tucson. In other words, facing the officers’
refusal to stop questioning him until they received the
answers they wanted, Doody succumbed by providing some
information that was suggested by the officers’ questions but
that the state now concedes is not true.

   Moreover, the state court’s characterization of the interro-
gation contains significant “unreasonable determination[s] of
the facts in light of the evidence presented in the State court
proceeding,” § 2254(d)(2), which, in part, undergirded the
state court’s conclusion that the confession was voluntary.
These factual errors contribute to our conclusion that the deci-
sion was unreasonable. See Wiggins v. Smith, 539 U.S. 510,
528 (2003) (“This partial reliance on an erroneous factual
finding further highlights the unreasonableness of the state
court’s decision.”).

  First, the state court — inexplicably — found that Doody
was “alert and responsive throughout the interrogation.”
Although there was testimony at the suppression hearing that
he was alert for at least portions of the interrogation, it is sim-

2000). Further, we express no opinion on whether the task force actively
sought to ensure that Doody’s stepfather would not learn of Doody’s inter-
rogation, as Doody argues. Nonetheless, it is indisputable that, despite
ample opportunity requiring no special effort, the task force failed to
notify a minor’s guardian of the minor’s impending interview with police
about his possible involvement in a multiple homicide.
15650                  DOODY v. SCHRIRO
ply wrong to characterize him as “responsive.” The tapes
reveal long stretches of silence — as long as ten minutes —
in the face of dozens of questions in a row. Indeed, the state
court decision later acknowledged that “Doody did not speak
for long periods during the interrogation,” a statement incon-
sistent with the earlier finding that he was “responsive
throughout.” As discussed above, Doody’s non-
responsiveness, and the officers’ relentless attempts to get
him to respond, weigh heavily in the voluntariness analysis.

   The state court also found that the officers’ questioning was
“courteous, [and] almost pleading.” Although the officers’
questions by and large were, as the state court noted, couched
in “pleading” language, their tones at times were far from
pleasant. Indeed, their tones varied from “pleading” to scold-
ing to sarcastic to demeaning to demanding. In any event, no
matter the tone, twelve hours of insistent questioning of a
juvenile by tag-teams of two, three and four officers became
menacing and coercive, and decidedly not “courteous.” And
some of their statements — particularly those which directly
preceded his confession — told Doody that he had to answer
their questions. Those statements were not “pleading[s]” —
they were commands. Nor is there anything “courteous,” or
merely “pleading,” about statements such as, “I’m gonna stay
here until I get an answer.”

   Finally, the state court found that, after only two and one-
half hours, Doody admitted that “he had borrowed Carat-
achea’s rifle at the time of the temple murders.” Not so.
Doody did admit around that time that he and Garcia bor-
rowed the gun for two days. But he stated that it was “close
to the end of June” that he borrowed the gun, more than a
month before the murders, and so indicated that he did not
have the gun “at the time of the temple murders.” This error
is of great significance. A key factor in this voluntariness
inquiry is the length of the interrogation before the confes-
sion. And, as it turns out, Doody did not confess to any con-
                       DOODY v. SCHRIRO                   15651
nection to the temple murders until over six hours of
interrogation.

                        *      *      *

   [12] A juvenile was given Miranda warnings in a down-
played manner that ensured he would not take them seriously
and would waive his rights. With only a flimsy version of the
protection the Miranda warnings are designed to provide, he
was then interrogated for more than twelve hours, overnight,
almost entirely without pause and with no friendly adult pres-
ent. He was told that he had to answer the officers’ questions
and that the interrogation would not end until he confessed.
He was finally broken down by the ceaseless questioning of
two, three, and four police officers, questioning that continued
despite his frequent long stretches of silence. Under these cir-
cumstances, we conclude, he did not voluntarily confess. The
state court’s holding to the contrary was, for the reasons we
have surveyed, an “objectively unreasonable” application of
clearly established federal law. See Williams, 529 U.S. at 409.

                              C.

  The state argues, in the alternative, that any error was
harmless. Because the Arizona courts found no error, they did
not reach the issue of harmlessness. Our review is therefore
de novo. See Rompilla v. Beard, 545 U.S. 374, 390 (2005);
Frantz v. Hazey, 533 F.3d 724, 736 (9th Cir. 2008) (en banc).

  [13] Confessions are indisputably damning evidence:

    A confession is like no other evidence. Indeed, “the
    defendant’s own confession is probably the most
    probative and damaging evidence that can be admit-
    ted against him. . . . [T]he admissions of a defendant
    come from the actor himself, the most knowledge-
    able and unimpeachable source of information about
    his past conduct.” . . . . In the case of a coerced con-
15652                   DOODY v. SCHRIRO
    fession . . . , the risk that the confession is unreliable,
    coupled with the profound impact that the confession
    has upon the jury, requires a reviewing court to exer-
    cise extreme caution before determining that the
    admission of the confession at trial was harmless.

Arizona v. Fulminante, 499 U.S. 279, 296 (1991) (first two
alterations in original) (quoting Bruton v. United States, 391
U.S. 123, 139-40 (1968) (White, J., dissenting)).

   [14] The state here relied heavily on Doody’s confession,
playing all seventeen tapes of the interrogation for the jury.
See Moore v. Czerniak, 534 F.3d 1128, 1147 (9th Cir. 2008)
(noting the particularly prejudicial impact of “a taped record-
ing of a defendant’s confession taken with all the requisite
formalities by police officers and played to a jury that hears
the defendant’s confession in the defendant’s own words from
his own lips”). Moreover, the prosecutor’s opening and clos-
ing statements reviewed and recounted the confession in great
detail. As the confession did not align with the state’s theory
of Doody’s role, the prosecutor carefully analyzed which por-
tions proved Doody’s involvement in the murders, and which
portions the state believed were lies.

   The strongest additional evidence against Doody was Gar-
cia’s testimony. But the jury plainly did not credit that testi-
mony. Garcia testified that Doody contemplated the murders
while planning the robbery, and, with premeditation, shot the
monks himself. The special verdict form, however, indicated
that Doody was convicted on felony-murder grounds, not for
premeditated murder. Significantly, the state, in its closing
statement, told the jurors that, if they believed only the ver-
sion of events set forth in Doody’s confession, they should
convict him of felony-murder. Doody thus could well have
been convicted on the basis of his confession alone.

  [15] Other than his confession and Garcia’s testimony, the
evidence against Doody was weak. Doody’s supposedly
                      DOODY v. SCHRIRO                   15653
incriminating statements to friends were, according to the wit-
nesses’ own testimony, understood as jokes. The evidence
linking him to items stolen from the temple depended almost
entirely on the testimony of friends of Caratachea’s who testi-
fied with immunity and not without self-interest, as the stolen
items had been linked to them. Stolen items found in Garcia’s
bedroom — which Doody shared at the time it was searched
— were not connected specifically to Doody.

   There was some circumstantial evidence that was some-
what more persuasive: One non-self-interested witness testi-
fied that Doody claimed ownership of one item stolen from
the temple. Also, an acquaintance of Doody’s testified that
Doody paid the witness $1,000 that he owed for a car shortly
after the murders, although before the murders he had been
unable to pay. But the defense impeached this testimony with
the witness’s prior statement that Doody had paid for the car
before the murders.

   [16] In sum, discounting Garcia’s testimony, as the jury
did, the state’s case relied almost entirely on his confession
and some peripheral, circumstantial evidence. We have no
difficulty in concluding that the erroneous admission of
Doody’s confession had a “substantial and injurious effect or
influence” on the jury’s verdict. Brecht, 507 U.S. at 623.

                   IV.   CONCLUSION

   For the foregoing reasons, we AFFIRM in part, REVERSE
in part, and REMAND with directions to grant the petition.
