United States v. Molina-Gomez , 781 F.3d 13 ( 2015 )


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  •           United States Court of Appeals
    For the First Circuit
    No. 13-1494
    UNITED STATES OF AMERICA,
    Appellee,
    v.
    JORGE L. MOLINA-GÓMEZ,
    Defendant, Appellant.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF PUERTO RICO
    [Hon. José A. Fusté, U.S. District Judge]
    Before
    Torruella, Lipez, and Barron,
    Circuit Judges.
    Leonardo M. Aldridge-Kontos, Assistant Federal Public
    Defender, with whom Héctor E. Guzmán-Silva, Jr., Federal Public
    Defender, Héctor L. Ramos-Vega, Assistant Federal Public Defender,
    and Liza L. Rosado-Rodríguez, Research and Writing Specialist, were
    on brief, for appellant.
    Juan Carlos Reyes-Ramos, Assistant United States Attorney,
    with whom Rosa Emilia Rodríguez-Vélez, United States Attorney, and
    Nelson Pérez-Sosa, Assistant United States Attorney, Chief,
    Appellate Division, were on brief, for appellee.
    March 20, 2015
    TORRUELLA,       Circuit     Judge.      Jorge   L.    Molina-Gómez
    ("Molina") appeals the district court's order denying his motion to
    suppress both the heroin discovered in hidden compartments of his
    laptop computer and Sony Playstation game console and some of the
    statements he made to United States Customs and Border Protection
    ("CBP") officers upon returning to Puerto Rico from Colombia.
    While we find no Fourth Amendment violation, Molina's statements
    made   during    further     secondary      questioning    regarding     drug
    trafficking activity should have been suppressed. As a result, his
    case must be remanded so that he can opt to withdraw his plea and
    proceed to trial should he choose to do so.
    I.     Background1
    On August 6, 2012, at approximately 11:00 p.m., Molina
    arrived at the Luis Muñoz Marín International Airport in San Juan,
    Puerto Rico, via Panama, after a five-day trip to Colombia.              This
    was the third time in four months in which Molina had taken a short
    trip to Colombia, a known source of illegal narcotics.                   As a
    result, the CBP computer system flagged Molina for questioning.
    Upon    deplaning,       Molina   was    referred     to   secondary
    inspection, where he claimed one carry-on bag, one computer case
    1
    Because this appeal follows a guilty plea, we draw the facts
    from the change-of-plea colloquy and the presentence investigation
    report, United States v. Cintrón-Echautegui, 
    604 F.3d 1
    , 2 (1st
    Cir. 2010), supplementing where necessary from the United States
    Immigration and Customs Enforcement ("ICE") Investigation Report.
    Notably, the parties do not dispute many of the material facts.
    -2-
    holding an ACER laptop computer, and one small bag containing a
    Sony Playstation.      The carry-on bag contained personal belongings,
    three cell phones, and a Western Union money gram in the amount of
    one million Colombian pesos (approximately $560) sent to Molina at
    the Hotel Galaxy the day after he arrived in Colombia by a
    Colombian man named Rodolfo Trochez Sardí.
    In   response    to   the    CBP    officers'   questions,    Molina
    explained that he traveled to Cartagena, Colombia, for four days to
    visit a friend, "Camilo," whom he met through another friend named
    Cynthia.    He stated that he purchased his ticket for $500 on the
    COPA Airlines website using a credit card, but that he did not have
    the credit card with him.         Molina told the CBP officers that while
    in Colombia he stayed at the Hotel Galaxy and did not leave his
    hotel   room,    but   rather     just    ate    and    played    games   on    his
    Playstation.
    These answers raised the CBP officers' suspicions, and
    further    questioning    and     investigation        revealed   problems     with
    Molina's story.     For example, Molina did not know either Camilo or
    Cynthia's last name.        And, contrary to his assertion, Molina did
    not purchase his plane ticket online via credit card, but rather it
    was purchased in cash at a Cali, Colombia travel agency.                  Indeed,
    all three of Molina's Colombian trips were booked with cash through
    this travel agency.
    -3-
    Molina was then escorted to a small (approximately ten-
    foot-by-ten-foot), windowless room containing one desk where he was
    patted down and subjected to further secondary questioning. He was
    in this room for approximately two hours and was asked about his
    trip to Colombia, his intentions upon reentry, and drug trafficking
    generally.     The record is unclear as to what specifically the CBP
    officers asked and what Molina's responses were.          He did, however,
    tell the officers that he had to work the following morning at
    8:00 a.m., and he denied any involvement in drug trafficking.
    While this questioning was ongoing, other CBP officers
    were inspecting Molina's belongings.            They X-rayed his laptop,
    Playstation, and three cell phones and saw no contraband.                They
    also confirmed that the electronics were all operational, but noted
    that while the laptop turned on, it contained no data despite being
    an older model.      A review of the three cell phones showed text
    messages from Camilo, Sardí, and numerous unidentified others.
    These   text     messages     involved     money   transactions       totaling
    approximately    $8,000     and   referenced   money   Molina   had    already
    received and money he would receive once he arrived in New York.
    The phones also revealed a confirmed plane ticket from San Juan to
    New York for 9:35 the following morning, contradicting Molina's
    statement to CBP officers that he would be working in San Juan at
    8:00 a.m.
    -4-
    Given all of these red flags, the officers suspected that
    Molina was smuggling narcotics.      Because the     pat-down yielded no
    results and the X-ray of Molina's electronics came back negative,
    the   officers   were   concerned   that   Molina    was   carrying   drugs
    internally.      They explained the situation to Molina, and he
    voluntarily consented to a medical exam.            At around 1:45 a.m.,
    Molina was taken, in shackles,2 to San Gerardo Hospital.         An X-ray
    exam was inconclusive, so a CT scan was performed and his bowel-
    movements were monitored. These tests confirmed that there were no
    foreign objects inside Molina's body.        Later that day, at around
    6:00 p.m., he was released from the hospital and transported back
    to the airport.
    Upon returning to the airport, Molina was released by CBP
    and allowed to enter the United States.        He was given all of his
    belongings except for the laptop and Playstation, which were
    detained for further examination by the CBP Forensics Laboratory
    because a dog-sniff "showed interest" in the laptop.           Molina was
    given a pamphlet explaining the electronic-device detention process
    and whom to contact to inquire about the property.
    The following day, August 8, the laptop and Playstation
    were received by the CBP Forensic Lab.              The detention ticket
    2
    Molina was not handcuffed or restrained during his initial
    questioning or during the inspections of his belongings. It is
    unclear whether he was handcuffed during the further two-hour
    questioning in the small, windowless room.
    -5-
    indicated that the detention was for "data extraction" but this was
    in error, as the electronics were detained in order to be searched
    for hidden contraband.           Indeed, no data extraction was ever
    conducted.    Beginning on August 11, Molina started calling the CBP
    to inquire about the status of his electronics and when they would
    be returned. On August 24, a CBP forensic chemist disassembled the
    electronics    and    found    black     bags   hidden   inside   sophisticated
    compartments of both the laptop and Playstation.                      The bags'
    contents tested positive for heroin -- 511 grams in the laptop and
    1.05 kilograms in the Playstation.
    On August 28, CBP, in coordination with ICE, called
    Molina to inform him that his electronics could be picked up at the
    airport.     When Molina arrived later that day, he was arrested by
    ICE agents.      The agents read Molina his rights, which Molina
    subsequently waived.        He confirmed that he owned both the laptop
    and the Playstation, that he took them to Colombia and intended to
    return with them, that he had planned to travel to New York the
    morning after he returned to Puerto Rico but never did so, and that
    his trip to Colombia and New York were paid for by Sardí.
    Molina   was     indicted    for   possession    with    intent   to
    distribute one kilogram or more of heroin, in violation of 21
    U.S.C. § 841(a)(1) & (b)(1)(A)(i), in September 2012.                In December
    2012, he filed a motion to suppress the heroin and any statements
    made during the further secondary questioning as violations of his
    -6-
    Fourth and Fifth Amendment rights, respectively.    The motion was
    denied via a brief text order, which stated in its entirety:
    I am of the opinion that the position advanced
    by the government in the opposition to the
    motion to suppress is correct as a matter of
    law. The Motion to Suppress is denied. If
    the defendant pleads, he may preserve the
    issue on appeal.
    Three days later, Molina entered a conditional plea pursuant to
    Rule 11(a)(2) of the Federal Rules of Criminal Procedure,3 and he
    now timely appeals the denial.
    3
    The rule states:
    With the consent of the court and the government, a
    defendant may enter a conditional plea of guilty or nolo
    contendere, reserving in writing the right to have an
    appellate court review an adverse determination of a
    specified pretrial motion. A defendant who prevails on
    appeal may then withdraw the plea.
    Fed. R. Crim. P. 11(a)(2). As there was no written plea agreement
    in this case, Rule 11(a)(2) was technically violated. However,
    Molina, the government, and the district court all understood that
    the plea was conditional upon Molina's right to appeal the
    suppression ruling. This was explicitly stated in the text order
    denying the motion to suppress and again at the change of plea
    hearing.   Thus, the violation is excused under Rule 11(h) as a
    harmless error. See Fed. R. Crim. P. 11(h) ("A variance from the
    requirements of this rule is harmless error if it does not affect
    substantial rights."). Other courts faced with this issue have
    likewise found a conditional plea valid despite the technical
    violation. See, e.g., United States v. Santiago, 
    410 F.3d 193
    ,
    197-98 (5th Cir. 2005); United States v. Markling, 
    7 F.3d 1309
    ,
    1313 (7th Cir. 1993).
    -7-
    II.   Discussion
    A.   Standard of Review
    "We review the [district] court's findings of fact for
    clear error and review de novo its conclusions of law and its
    rulings on the constitutionality of the government's conduct."
    United States v. Beras, 
    183 F.3d 22
    , 25 (1st Cir. 1999); see also
    United States v. Carrigan, 
    724 F.3d 39
    , 45 (1st Cir. 2013) (Fourth
    Amendment); United States v. Mittel-Carey, 
    493 F.3d 36
    , 39 (1st
    Cir. 2007) (Fifth Amendment).    Because the district court made no
    findings of fact, the entire record is reviewed de novo.     United
    States v. Robles, 
    45 F.3d 1
    , 5 (1st Cir. 1995).     So long as "any
    reasonable view of the evidence supports it," we will uphold the
    denial of the motion to suppress. United States v. Brown, 
    510 F.3d 57
    , 64 (1st Cir. 2007) (internal quotation marks and citation
    omitted).
    B.   The Search of the Electronics
    Molina first argues that the search of his laptop and
    Playstation, which uncovered the hidden heroin, was an unreasonable
    search in violation of the Fourth Amendment to the United States
    Constitution.   Pursuant to the Fourth Amendment,
    The right of the people to be secure in their
    persons, houses, papers, and effects, against
    unreasonable searches and seizures, shall not
    be violated, and no Warrants shall issue, but
    upon probable cause, supported by Oath or
    affirmation, and particularly describing the
    place to be searched, and the persons or
    things to be seized.
    -8-
    U.S. Const. amend. IV.         It is well established, however, that "the
    Fourth Amendment's balance of reasonableness is qualitatively
    different at the international border than in the interior" due to
    the "longstanding concern for the protection of the integrity of
    the border."     United States v. Montoya de Hernández, 
    473 U.S. 531
    ,
    538 (1985).      This concern is, "if anything, heightened by the
    veritable national crisis in law enforcement caused by smuggling of
    illicit narcotics."           
    Id. As a
    result, there is a recognized
    "border search exception" to the warrant requirement.                     See United
    States v. Ramsey, 
    431 U.S. 606
    , 619-22 (1977); see also Montoya de
    
    Hernández, 473 U.S. at 538
    ;      
    Beras, 183 F.3d at 25-26
    .
    International airports such as the Luis Muñoz Marín International
    Airport are the "functional equivalent" of an international border
    and are thus subject to this exception.                  
    Robles, 45 F.3d at 5
    ;
    United States v. Uricoechea-Casallas, 
    946 F.2d 162
    , 164 (1st Cir.
    1991).
    Under the border search exception, "[r]outine searches of
    the   persons    and   effects      of   entrants   are      not    subject    to   any
    requirement of reasonable suspicion, probable cause, or warrant."
    Montoya de 
    Hernández, 473 U.S. at 538
    ; see also United States v.
    Braks, 
    842 F.2d 509
    , 514 (1st Cir. 1988) ("The First Circuit
    standard   for    routine      border    searches       is   the    'no   suspicion'
    standard.").     These searches "are reasonable simply by virtue of
    the fact they occur at the border."                 United States v. Flores-
    -9-
    Montano, 
    541 U.S. 149
    , 152-53 (2004) (quoting 
    Ramsey, 431 U.S. at 616
    ).     Non-routine     searches,      by    contrast,   require    reasonable
    suspicion. Montoya de 
    Hernández, 473 U.S. at 541-42
    ; United States
    v. Barrow, 
    448 F.3d 37
    , 41 (1st Cir. 2006).                Though there is no
    hard-and-fast rule, and the Supreme Court has cautioned against
    "[c]omplex balancing tests," 
    Flores-Montano, 541 U.S. at 152
    ,
    whether a search qualifies as "routine" or "not routine" often
    depends on the "degree of invasiveness or intrusiveness associated
    with" the search.        
    Braks, 842 F.2d at 511-12
    (listing numerous
    factors to consider).           For example, searches that are "highly
    intrusive searches of the person," 
    Flores-Montano, 541 U.S. at 152
    ,
    such as strip searches and body cavity searches, have been deemed
    to be non-routine.       E.g., id.; 
    Barrow, 448 F.3d at 41
    ; 
    Braks, 842 F.2d at 512-13
    ; United States v. Kallevig, 
    534 F.2d 411
    , 413-14
    (1st    Cir.   1976).      So    have    searches    of    property     that   are
    "destructive," 
    Flores-Montano, 541 U.S. at 155-56
    , such as drilling
    a hole in a metal cylinder.         
    Robles, 45 F.3d at 5
    .         By contrast,
    pat-downs, 
    Braks, 842 F.2d at 513
    , searching luggage inside an
    aircraft's     cargo    hold,   
    Uricoechea-Casallas, 946 F.2d at 165
    ,
    opening bottles of liquor and testing the contents, 
    Barrow, 448 F.3d at 41
    , and removing, disassembling, and reassembling a fuel
    tank without causing damage, 
    Flores-Montano, 541 U.S. at 154-55
    ,
    have all been deemed routine searches.
    -10-
    Here, Molina argues that the search of his laptop and
    Playstation that led to the discovery of the two heroin bags
    constitutes a non-routine and unreasonable search.        However, he is
    unable to point to any specific act that is either non-routine or
    unreasonable.   Instead, his argument seems to be that because the
    initial X-ray and search of his laptop and Playstation turned up
    negative, and because his eighteen-hour detention at the hospital
    (to which he consented) showed that he was not carrying drugs
    internally, it was therefore unreasonable to detain his laptop and
    Playstation for further testing. And, even if it was reasonable to
    further   detain   the   electronics    initially,   he   contends,   the
    detention became unreasonable during the twenty-two days they were
    at the CBP lab.    The government, for its part, counters that the
    search qualifies as a routine border search and thus no suspicion
    at all -- let alone reasonable suspicion -- was necessary, but even
    if reasonable suspicion was necessary, that standard was satisfied.
    We need not categorize the search as either routine or
    non-routine because we agree with the government that even assuming
    the search was non-routine, reasonable suspicion existed to justify
    the search.   Reasonable suspicion exists when agents "demonstrate
    some objective, articulable facts that justify the intrusion as to
    the particular person and place searched."       
    Robles, 45 F.3d at 5
    (quoting 
    Uricoechea-Casallas, 946 F.2d at 166
    ); see also Montoya de
    
    Hernández, 473 U.S. at 541-42
    (describing reasonable suspicion as
    -11-
    a   "common-sense   conclusio[n]   about       human   behavior   upon     which
    practical people, -- including government officials, are entitled
    to rely" (alteration in original) (quoting New Jersey v. T.L.O.,
    
    469 U.S. 325
    , 346 (1985)) (internal quotation marks omitted)).
    Such objective, articulable facts are present here.
    First, this was Molina's third trip in four months (each only for
    a matter of days) to Colombia, a country known for its connection
    to drug smuggling.     Second, Molina gave odd and suspicious answers
    to routine Customs questions.       These answers ranged from highly
    dubious -- (1) he could not remember the last name of either the
    friend he was visiting (Camilo) or the friend who introduced them
    (Cynthia); and (2) all he did while in Colombia was stay in the
    hotel and play with his Playstation –- to assertions proven to be
    flat-out lies -- (3) he claimed to have purchased his ticket online
    with a credit card but in actuality paid for it in cash at a travel
    agency; and (4) he claimed to be working in Puerto Rico the next
    morning but in fact had a confirmed flight to New York City.
    Third, his laptop was old and operational, yet it contained no
    data.   Finally, his phones contained text messages involving prior
    and future money transactions.     Taken together, these facts easily
    give rise to a reasonable suspicion that Molina was attempting to
    smuggle   narcotics.     See   
    Robles, 45 F.3d at 5
      (holding    that
    reasonable suspicion existed where a metal machine part of no
    commercial value was shipped "from Colombia -- a known source
    -12-
    country for narcotics" to a residence in the United States at a
    cost higher than its worth, without insurance); United States v.
    Lamela, 
    942 F.2d 100
    , 102 (1st Cir. 1991) (finding reasonable
    suspicion where defendant, among other things, "was a passenger
    aboard an international flight originating in Colombia" and "gave
    inconsistent responses to routine questions relating to the purpose
    of his travel"); 
    Kallevig, 534 F.2d at 414
    (explaining that the
    "pattern and brevity of [defendant's] recent visits to countries
    considered to be important sources of drugs" was "properly noted"
    as a relevant factor in evaluating reasonable suspicion).
    That the initial X-ray of the electronics and the X-ray,
    CT scan, and bowel monitoring of Molina came up negative in no way
    alters this conclusion or transforms a legitimate and proper search
    into an unreasonable one.             "Authorities must be allowed 'to
    graduate     their    response   to    the   demands   of    any   particular
    situation,'" Montoya de 
    Hernández, 473 U.S. at 542
    (quoting United
    States v. Place, 
    462 U.S. 696
    , 709 n.10 (1983)), and that is
    precisely what the CBP officers did here.                   The officers had
    reasonable suspicion that Molina was smuggling drugs; they just did
    not   know    where   the   drugs     were   hidden.    There      is   nothing
    unreasonable about the officers shifting their attention back to
    the electronics and giving them a more in-depth look once they were
    satisfied that the drugs were neither on nor in Molina's body.              To
    the contrary, this approach is eminently reasonable when one
    -13-
    considers that a dog-sniff conducted while Molina was at the
    hospital showed interest in his laptop.
    Similarly, the search did not become unreasonable during
    the twenty-two days the electronics were detained.          The Supreme
    Court   has    "consistently   rejected   hard-and-fast   time   limits,"
    instead placing an emphasis on "'common sense and ordinary human
    experience.'"      
    Id. at 543
    (quoting United States v. Sharpe, 
    470 U.S. 675
    , 685 (1985)); see also 
    Flores-Montano, 541 U.S. at 155
    n.3
    (noting that "[r]espondent points to no cases indicating the Fourth
    Amendment shields entrants from inconvenience or delay at the
    international border").     Though twenty-two days does seem lengthy,
    it is not unreasonable under these circumstances.           We will not
    second-guess the techniques used by the CBP lab and require that a
    faster alternative -- which could have damaged the electronics
    during the disassembly and reassembly process, could have put an
    unnecessary budgetary and workload strain on the lab, or could even
    have failed to detect the expertly hidden heroin -- be employed.4
    See Montoya de 
    Hernández, 473 U.S. at 542
    ("[C]ourts should not
    indulge in 'unrealistic second-guessing,' . . . . '[T]he fact that
    the protection of the public might, in the abstract, have been
    4
    We note that while Molina's laptop and Playstation were detained
    for twenty-two days, Molina himself was allowed entry into the
    United States upon his return from the hospital. It would be a
    different situation -- one we take no position on -- if Molina
    himself was also forced to stay in detention during the twenty-two
    days his laptop was being held by CBP.
    -14-
    accomplished by 'less-intrusive' means does not, in itself, render
    the search unreasonable.'" (quoting 
    Sharpe, 470 U.S. at 686
    , 687));
    
    id. at 544
    (explaining that the Customs officers were not required
    by the Fourth Amendment to "simply shrug [their] shoulders" and
    allow an alimentary canal smuggling defendant into the interior
    because she had been detained for too long before passing cocaine-
    filled balloons (quoting Adams v. Williams, 
    407 U.S. 143
    , 145
    (1972))).   Thus, the search of Molina's laptop and Playstation did
    not violate his Fourth Amendment rights.
    C.   The Further Secondary Questioning
    Molina also argues that the further secondary questioning
    conducted by the CBP officers in a small, windowless room violated
    his Fifth Amendment rights because he was not given his Miranda
    warnings prior to being questioned.5     We agree.6
    "The Supreme Court developed the Miranda rules as a
    prophylactic measure to dissipate the coercion inherent in the
    custodial interrogation setting, with a goal of ensuring that any
    5
    Molina concedes that the initial questioning by the CBP officers
    prior to being moved to this room was permissible.
    6
    When Molina moved to suppress his statements in the district
    court, the government failed to respond. Molina thus argues that
    the government has waived any opposition to their suppression. We
    disagree. By denying Molina's motion to suppress, the district
    court "implicitly for[gave] any waiver that may have occurred."
    United States v. Scott, 
    705 F.3d 410
    , 416 (9th Cir. 2012). In
    similar circumstances, we have reached the merits of allegedly
    waived arguments, and we will do so here as well.      See United
    States v. Del-Valle, 
    566 F.3d 31
    , 37-38 (1st Cir. 2009).
    -15-
    statements made by a suspect are 'truly the product of free
    choice'" and consistent with the Fifth Amendment to the United
    States Constitution.    United States v. Vázquez, 
    857 F.2d 857
    , 861
    (1st Cir. 1988) (quoting Miranda v. Arizona, 
    384 U.S. 436
    , 457, 458
    (1966)).   Accordingly, "[i]t is well established that Miranda
    warnings must be communicated to a suspect before he is subjected
    to 'custodial interrogation.'"        United States v. Nai Fook Li, 
    206 F.3d 78
    , 83 (1st Cir. 2000).      Both "custody" and "interrogation"
    must be present to require Miranda warnings.             See, e.g., United
    States v. Fernández-Ventura, 
    85 F.3d 708
    , 710 (1st Cir. 1996)
    ("Fernández-Ventura I").
    Custody   exists   where    there   is   "a   formal   arrest   or
    restraint on freedom of movement of the degree associated with a
    formal arrest."      
    Id. (internal quotation
    marks and citations
    omitted). Though custody is a somewhat amorphous concept, relevant
    considerations in a custody determination include, but are not
    limited to, "whether the suspect was questioned in familiar or at
    least neutral surroundings, the number of law enforcement officers
    present at the scene, the degree of physical restraint placed upon
    the suspect, and the duration and character of the interrogation."
    
    Id. at 711
    (quoting United States v. Masse, 
    816 F.2d 805
    , 809 (1st
    Cir. 1987)).
    In the border context, we also "must take into account
    the strong governmental interest in controlling our borders."
    -16-
    United States v. Fernández-Ventura, 
    132 F.3d 844
    , 846 (1st Cir.
    1998) ("Fernández-Ventura II"). As a result, the rules surrounding
    Miranda at the border are more relaxed.    See United States v. Long
    Tong Kiam, 
    432 F.3d 524
    , 529 (3d Cir. 2006) ("[N]ormal Miranda
    rules simply cannot apply to this unique situation at the border.
    This is a situation utterly unlike a normal law enforcement
    setting." (internal citation omitted)).    "[E]vents which might be
    enough to signal 'custody' away from the border will not be enough
    to establish 'custody' in the context of entry into [t]he country."
    Fernández-Ventura 
    II, 132 F.3d at 847
    (quoting United States v.
    Moya, 
    74 F.3d 1117
    , 1120 (11th Cir. 1996)).       For example, even
    though a traveler being questioned by CBP is not "free to leave,"
    he is not necessarily in custody. See Fernández-Ventura 
    I, 85 F.3d at 711
    ("[E]ven secondary inspection does not per se constitute
    custodial interrogation."); 
    id. at 712
    (explaining that it "is
    simply wrong" to conclude that a traveler is in custody because
    they "may not simply walk away from an interrogating officer"
    (internal quotation marks omitted)); see also United States v.
    Butler, 
    249 F.3d 1094
    , 1100 (9th Cir. 2001) ("[T]he mere detention
    of a person in a border station's security office from which he or
    she is not free to leave, while a search of a vehicle occurs, is
    not 'custody' for [Miranda] purposes.").
    "Relaxed" rules, however, do not mean no rules, and a
    review of the record persuades us that, given the totality of the
    -17-
    circumstances, Molina was, indeed, in custody during this further
    secondary questioning.       First, Molina was placed in a small,
    windowless room, approximately ten-feet-by-ten-feet, with at least
    two CBP officers.     As we noted in United States v. Pratt, 
    645 F.2d 89
    , 90 (1st Cir. 1981), the "confining character of a [C]ustoms
    questioning   cell,    combined   with   isolation   with   two   probing
    inspectors, . . . creates an oppressive atmosphere that we [cannot]
    ignore."
    Second, Molina was held in this room for between one-and-
    a-half and two hours. Though this is "never a singly determinative
    factor," 
    id. at 91,
    the longer someone is detained, the more likely
    he is in custody.     Compare 
    id. at 90-91
    (finding that a fifteen-
    minute encounter "supports a characterization of routine [C]ustoms
    inquiry rather than custodial interrogation"), and Borodine v.
    Douzanis, 
    592 F.2d 1202
    , 1208 (1st Cir. 1979) (finding that a ten-
    minute encounter was not custodial and referring to similar cases
    involving encounters of seventeen-minutes and twenty-minutes), with
    United States v. García, 
    496 F.2d 670
    , 672-73 (5th Cir. 1974)
    (holding an encounter to be custodial where detention lasted "for
    at least an hour").    But see Fernández-Ventura 
    II, 132 F.3d at 848
    (finding that a one-hour-and-twenty-minute encounter was "not
    extraordinary" and did not establish custody where the record did
    not support defendant's allegation that he was "subjected to
    'focused questioning'" for that entire time).
    -18-
    Third, the questioning was not "routine."            The CBP
    officers were no longer probing whether or not to admit Molina into
    the country, as they had already reviewed Molina's travel documents
    and therefore confirmed his U.S. citizenship.       Instead, they were
    probing   their   suspicions   of    Molina's   involvement   with   drug
    smuggling activity.     Cf. 
    Pratt, 645 F.2d at 91
    (finding that
    because, among other things, "[n]o events transpired to create or
    to symbolize a high and evident degree of suspicion about the
    appellant by the agents," the encounter did "not transgress the
    limits that case law has permitted in the absence of Miranda
    warnings").7
    Taken together, we conclude that this encounter -- which
    involved a lengthy detention in a small, windowless room and
    probing questions about potential illegal activity -- went above
    and beyond a routine Customs inspection to determine whether or not
    Molina should be admitted into the United States.       Instead, it was
    akin to "'a formal arrest or restraint on freedom of movement of
    7
    Molina also claims that he was handcuffed to the desk throughout
    the entire encounter. The government, meanwhile, counters that
    there was no evidence that Molina was handcuffed, outside of his
    own self-serving statement. It adds that the surveillance video
    shows Molina leaving the secondary area, being escorted to his
    carry-on belongings, and returning to the secondary area without
    restraints; it was not until Molina was transported to the hospital
    that video footage shows him shackled.      Because the government
    never directly refutes that Molina was handcuffed, this
    consideration is, at best, ambiguous.     Hence, we cannot factor
    whether Molina was handcuffed into our evaluation of whether he was
    in custody.
    -19-
    the degree associated with a formal arrest.'" Fernández-Ventura 
    I, 85 F.3d at 710
    (quoting Thompson v. Keohane, 
    516 U.S. 99
    , 112
    (1995)).   Thus, Molina was in custody for Miranda purposes.
    Being in custody, however, is only half the equation.
    Molina must still prove that he was subject to interrogation.
    "Interrogation   refers   to   both        express    questioning      and   its
    'functional equivalent,' which includes 'any words or actions on
    the part of the police (other than those normally attendant to
    arrest and custody) that the police should know are reasonably
    likely to elicit an incriminating response from the suspect.'" 
    Id. at 711
    (quoting Rhode Island v. Innis, 
    446 U.S. 291
    , 301 (1980)).
    At the same time though, "questions from [Customs] officials are
    especially understood to be a necessary and important routine for
    travelers arriving at American entry points." Id.; see also 
    Pratt, 645 F.2d at 90
    (explaining that individuals "approach official
    [airport   Customs   inspections]    inquiry     knowing    of   its    greater
    necessity and routine").       "This understanding cuts against the
    potentially coercive aspect of the Customs inquiry, and [thus]
    lessens the need for Miranda warnings."              Fernández-Ventura 
    I, 85 F.3d at 711
    ; see also Long Tong 
    Kiam, 432 F.3d at 529
    ("We now
    reaffirm the well-established authority of border inspectors to ask
    questions of those entering the United States.").             As a result, a
    "careful examination of all the circumstances" is needed in order
    -20-
    to distinguish between "routine Customs questioning and custodial
    interrogation."       Fernández-Ventura 
    I, 85 F.3d at 711
    .
    Here, the record is unclear as to what exactly Molina was
    asked during secondary questioning.                 He claims, however -- and the
    government does not contest -- that he was asked general questions
    regarding    his    reasons      for   traveling       to    another     country,    his
    activities while there, his reasons for entering the United States,
    and his involvement in drug-trafficking activities.                      According to
    Molina, this was all "interrogation" because he was in custody
    during the further secondary questioning, and thus "all statements"
    made while in the small windowless room must be suppressed.
    Molina's      position     is    far    too    broad.       Some   of   the
    questions    asked,       such   as    Molina's      reasons      for    traveling    to
    Colombia, what he did while there, and why he decided to return
    when he did, were routine questions which we have held do not
    constitute interrogation. See, e.g., 
    id. at 710
    ("[I]n the Customs
    context,    we     have    stated      that   questions       from      officials    are
    especially understood to be a necessary and important routine for
    travelers arriving at American entry points."); United States v.
    Tajeddini, 
    996 F.2d 1278
    , 1287-88 (1st Cir. 1993) (asking "where [a
    traveler] was arriving from and with whom he was traveling"
    constitute    "routine      Customs      questions"         not   requiring     Miranda
    warnings); United States v. Ledezma-Hernández, 
    729 F.2d 310
    , 313
    (5th Cir. 1984) (finding that routine questioning at the border as
    -21-
    to the traveler's destination and the contents of his truck was not
    custodial interrogation).       Indeed, these are the same questions
    Molina was asked during his initial questioning, and he has
    conceded that they were appropriate questions.
    The CBP officers' questioning into Molina's involvement
    with drug activity, however, is more problematic.          This line of
    questioning had nothing to do with whether or not to admit Molina
    into the country.     Instead, these questions "symbolize[d] a high
    and evident degree of suspicion" by the CBP officers.        Cf. 
    Pratt, 645 F.2d at 90
    -91 (finding that limited questioning seeking an
    explanation as to why the traveler possessed a ticket issued for
    another person was routine and did not "create or . . . symbolize
    a high and evident degree of suspicion about the appellant").        The
    officers were already leery that Molina may have been involved in
    drug trafficking, and this line of questioning was clearly aimed at
    eliciting an incriminating response.      See 
    Innis, 446 U.S. at 301
    ;
    Fernández-Ventura 
    I, 85 F.3d at 710
    -12 (finding that questions by
    Customs agents into "whether [the defendants were] carrying any
    money" would "quite clearly . . . constitute[] interrogation" if
    the defendants were in custody); see also Long Tong 
    Kiam, 432 F.3d at 530
    (explaining that interrogation begins once "the inspector's
    questions objectively cease to have a bearing on the grounds for
    admissibility   and   instead   only   further   a   potential   criminal
    -22-
    prosecution").    The questions regarding Molina's drug trafficking
    activities, therefore, constituted interrogation.
    Because    Molina    was    in    custody      during    the    further
    secondary     questioning    and     the      questions     relating       to   drug
    trafficking    constituted      interrogation,       the    CBP     officers    were
    required to give Molina his Miranda warnings.                     See Fernández-
    Ventura 
    I, 85 F.3d at 710
    .          Their failure to do so constituted a
    Fifth Amendment violation, and as a result any statements made by
    Molina in response to these questions should have been suppressed
    by the district court.8
    III.      Conclusion
    Molina's motion to suppress the heroin seized from his
    laptop and Playstation was properly denied, as was his motion to
    suppress regarding the statements made during his further secondary
    questioning as to his travels to and from Colombia and his plans
    upon reentry.    The statements regarding Molina's drug trafficking
    activity,   however,    should      have     been   suppressed.        Given     the
    remaining admissible evidence against Molina, it is highly unlikely
    that the suppression of these statements regarding drug trafficking
    8
    It is irrelevant that Molina's responses to the drug-trafficking
    interrogation were not incriminating.      As the Supreme Court
    explained in Miranda, "no distinction may be drawn between
    inculpatory statements and statements alleged to be merely
    'exculpatory'" because even "statements merely intended to be
    exculpatory by the defendant are often used to impeach his
    testimony at trial or to demonstrate untruths in the statement
    given." 
    Miranda, 384 U.S. at 477
    .
    -23-
    activity -- activity that Molina emphatically denied at the time --
    would have affected his decision to plead guilty.        Still, that is
    not our decision to make.          As we explained in United States v.
    Weber, "a court has no right to decide for a defendant that his
    decision [to plead guilty] would have been the same had the
    evidence the court considers harmless not been present."        
    668 F.2d 552
    , 562 (1st Cir. 1981) (adopting the rationale of the Seventh
    Circuit   and   numerous   state    courts).   Molina   is   entitled   to
    determine for himself whether he still wishes to plead guilty given
    the suppression of the drug-trafficking-related statements, and,
    therefore, his case is remanded so he may have the option of
    withdrawing his plea and proceeding to trial should he choose to do
    so.
    REMANDED.
    -24-