                     FOR PUBLICATION
  UNITED STATES COURT OF APPEALS
       FOR THE NINTH CIRCUIT

UNITED STATES OF AMERICA,                         No. 03-10307
                Plaintiff-Appellee,                  D.C. No.
               v.                                CR-02-00053-1-
EDWARD ROSENTHAL,                                      CRB
             Defendant-Appellant.
                                           

UNITED STATES OF AMERICA,                         No. 03-10370
               Plaintiff-Appellant,                 D.C. No.
               v.                                CR-02-00053-3-
EDWARD ROSENTHAL,                                      CRB
            Defendant-Appellee.
                                                   OPINION


         Appeal from the United States District Court
           for the Northern District of California
         Charles R. Breyer, District Judge, Presiding

                  Argued and Submitted
       September 13, 2005—San Francisco, California

                       Filed April 26, 2006

       Before: Betty B. Fletcher, John R. Gibson,* and
             Marsha S. Berzon, Circuit Judges.

                  Opinion by Judge B. Fletcher

   *The Honorable John R. Gibson, Senior United States Circuit Judge for
the Eighth Circuit, sitting by designation.

                                 4745
4748             UNITED STATES v. ROSENTHAL


                         COUNSEL

Dennis P. Riordan, Donald M. Horgan, and Joseph D. Elford,
San Francisco, California, for the appellant.

Amber S. Rosen, George L. Bevan, Jr., Hannah Horsley, and
Kevin V. Ryan, U.S. Attorney’s Office, San Jose, California,
for the appellee.


                         OPINION

B. FLETCHER, Circuit Judge:

   Edward Rosenthal appeals a three-count conviction for vio-
lations of the Controlled Substances Act (“CSA”), 21 U.S.C.
§§ 801 et seq., asserting an as-applied Commerce Clause
challenge, a claim of immunity pursuant to 21 U.S.C.
§ 885(d), erroneous evidentiary rulings and instructions by the
                  UNITED STATES v. ROSENTHAL                4749
district court, prosecutorial misconduct, juror misconduct, and
the improper denial of a hearing under Franks v. Delaware,
438 U.S. 154 (1978). The government cross-appeals, claiming
that the district court erroneously found Rosenthal eligible for
the “safety valve” and erroneously departed downward to
impose a single day of confinement.

   We have jurisdiction pursuant to 28 U.S.C. § 1291 and 18
U.S.C. § 3742(b), and we reverse the conviction solely on the
issue of jury misconduct. We affirm the district court on all
other grounds and dismiss the government’s claims regarding
sentencing as moot.

                               I

   In November 1996, Californians passed, by voter initiative,
Proposition 215, the Compassionate Use Act, which allows
patients to obtain marijuana for “personal medical purposes
. . . upon the written or oral recommendation or approval of
a physician.” CAL. HEALTH & SAFETY CODE § 11362.5(d). One
of the purposes of the Compassionate Use Act is

    [t]o ensure that seriously ill Californians have the
    right to obtain and use marijuana for medical pur-
    poses where that medical use is deemed appropriate
    and has been recommended by a physician who has
    determined that the person’s health would benefit
    from the use of marijuana in the treatment of cancer,
    anorexia, AIDS, chronic pain, spasticity, glaucoma,
    arthritis, migraine, or any other illness for which
    marijuana provides relief.

Id. The statute shields patients and their primary caregivers
from prosecution under state-law provisions outlawing the
possession and cultivation of marijuana. See id. § 11362.5(d).
4750               UNITED STATES v. ROSENTHAL
                                 A

   After passage of the Compassionate Use Act, a number of
“medical cannabis dispensaries” were formed to make mari-
juana accessible to seriously ill patients. In support of those
efforts, the Oakland City Council, on July 28, 1998, adopted
Ordinance No. 12076 (“the Oakland Ordinance”), which
intends to “ensure access to safe and affordable medical can-
nabis pursuant to the Compassionate Use Act of 1996.” Oak-
land, Cal., Ordinance 12076 § 1(C) (July 28, 1998) (codified
as amended at OAKLAND, CAL., MUN. CODE ch. 8.46). The
Oakland Ordinance purports to “provide immunity to medical
cannabis provider associations pursuant to Section 885(d) of
Title 21 of the United States Code.” Id. § 1(D). Under the
Ordinance, the City Manager designates “one or more entities
as a medical cannabis provider association.”1 That entity
would then designate individuals to help distribute medical
cannabis to seriously ill persons.

   The City of Oakland designated the Oakland Cannabis
Buyers’ Cooperative (“OCBC”) an official medical-cannabis-
provider association. Jeffrey Jones, OCBC’s executive direc-
tor, designated Rosenthal to be an agent of the OCBC and to
cultivate marijuana plants for distribution to authorized
medical-cannabis users. That designation, memorialized in a
letter from Jones to Rosenthal on September 4, 1998, specifi-
cally states that “you are deemed a duly authorized ‘officer of
the City of Oakland’ and as such are immune from civil and
criminal liability under Section 885(d) of the federal Con-
trolled Substances Act.”

                                  B

  After California’s approval of the Compassionate Use Act,
  1
   A 2004 amendment to the Oakland Ordinance states that “the City
Manager shall designate not more than one entity as a medical cannabis
provider association.”
                     UNITED STATES v. ROSENTHAL                      4751
questions surfaced as to whether cannabis dispensaries actu-
ally were immune from prosecution under state and federal
drug laws. In 1997, a California Court of Appeal held that
cannabis-cultivating clubs are not “primary caregivers” within
the meaning of the Compassionate Use Act and are therefore
not shielded from prosecution under the state’s controlled-
substances laws. See People ex rel. Lungren v. Peron, 70 Cal.
Rptr. 2d 20, 31-32 (Ct. App. 1997).2 On May 19, 1998, the
same district court from which the instant appeal is taken
entered a preliminary injunction order barring the OCBC (and
five other cannabis dispensaries) from manufacturing, distrib-
uting, or possessing marijuana with the intent to manufacture
or distribute, in violation of federal law. See United States v.
Cannabis Cultivators Club, 5 F. Supp. 2d 1086, 1106 (N.D.
Cal. 1998).

  The OCBC, after designation as an official cannabis dis-
pensary, sought dismissal of the complaint, but the district
court denied that request, rejecting the OCBC’s claim that the
Oakland Ordinance immunized it from federal liability under
21 U.S.C. § 885(d). The district court further denied OCBC’s
requests to modify the injunction to permit an exception in
cases of medical necessity.3

   Rosenthal continued cultivating marijuana for distribution
  2
     The California Supreme Court denied review of the case on February
25, 1998. Peron, 70 Cal. Rptr. at 20.
   3
     This court reversed and remanded the district court’s denial of OCBC’s
motion to modify, holding that the medical necessity defense was avail-
able and that the injunction could be modified to accommodate this
defense. See United States v. Oakland Cannabis Buyers’ Coop., 190 F.3d
1109, 1115 (9th Cir. 1999). On May 14, 2001, the Supreme Court
reversed, holding that “medical necessity is not a defense to manufactur-
ing and distributing marijuana” under the CSA. United States v. Oakland
Cannabis Buyers’ Coop., 532 U.S. 483, 494 (2001). The Court also held
that the district court had no authority to consider a medical necessity
defense in exercising its equitable powers, as such consideration was pre-
cluded by the CSA. Id. at 498-99.
4752              UNITED STATES v. ROSENTHAL
to both the OCBC and San Francisco’s Harm Reduction Cen-
ter from October 2001 until February 12, 2002, the day of his
arrest.

                               C

   Rosenthal filed a series of pre-trial motions and, eventually,
a motion to dismiss the indictment. He claimed his prosecu-
tion exceeded the federal government’s powers under the
Commerce Clause, violating the Tenth Amendment to the
U.S. Constitution; that the government engaged in selective
prosecution; that he was immune from prosecution under the
federal immunity provision; and that the indictment was
tainted due to entrapment-by-estoppel. The district court
denied all of Rosenthal’s motions. It also granted the govern-
ment’s motions in limine, which precluded Rosenthal from
putting on a “medical marijuana” defense, introducing evi-
dence or argument aimed at jury nullification, or introducing
evidence or argument related to an entrapment-by-estoppel
defense.

                               D

   On January 31, 2003, at the conclusion of the trial, the jury
found Rosenthal guilty of one count of manufacturing mari-
juana, in violation of 21 U.S.C. § 841(a)(1); one count of con-
spiracy to manufacture marijuana, in violation of 21 U.S.C.
§ 846; and one count of maintaining a place for the manufac-
ture of marijuana, in violation of 21 U.S.C. § 856(a)(1).

  Rosenthal moved for a new trial pursuant to Federal Rule
of Criminal Procedure 33, arguing that the court erred by
excluding his defense of entrapment by estoppel; the court
improperly excluded 19 jurors who expressed pro-medical-
marijuana beliefs; the court erroneously instructed the jury
regarding its right to engage in nullification; and Rosenthal
was entitled to a new trial because of juror and prosecutorial
misconduct. As to juror misconduct, Rosenthal submitted dec-
                    UNITED STATES v. ROSENTHAL                      4753
larations from two jurors, one of whom, on the eve of the ver-
dict, consulted with an attorney-friend who admonished the
juror to follow the judge’s instructions or risk “get[ting] into
trouble.” The district court held an evidentiary hearing on
April 1 and 8, 2003, and denied the motion for a new trial in
a published order. See United States v. Rosenthal, 266 F.
Supp. 2d 1068 (N.D. Cal. 2003) (“Rosenthal I”).

   On June 4, 2003, the district court sentenced Rosenthal to
one day of imprisonment. See United States v. Rosenthal, 266
F. Supp. 2d 1091 (N.D. Cal. 2003) (“Rosenthal II”). The court
found Rosenthal eligible for safety-valve relief pursuant to
United States Sentencing Guidelines § 5C1.2, entitling him to
a sentence below the mandatory five-year minimum. See id.
at 1097. The court departed downward by ten levels based on
the determination that Rosenthal honestly and reasonably
believed he was not disobeying federal law given the prom-
ises made by Oakland officials. See id. at 1098-100. Rosen-
thal was sentenced to three concurrent sentences of one day,
with credit for time served.

                                   II

   Rosenthal raises a claim of immunity pursuant to 21 U.S.C.
§ 885(d), challenges to the district court’s evidentiary rulings
and instructions regarding argument, claims of prosecutor and
juror misconduct, and the denial of a Franks hearing.4 The
government cross-appeals, arguing that the district court erred
in finding that Rosenthal was eligible for the “safety valve”
and in departing from the minimum sentence to impose a sin-
gle day of confinement.
  4
   Rosenthal originally raised an as-applied Commerce Clause challenge
but abandoned it during oral argument in light of Gonzales v. Raich, 125
S. Ct. 2195 (2005) (upholding application of CSA to intrastate cultivation
of marijuana plants for medicinal purposes).
4754              UNITED STATES v. ROSENTHAL
                              III

   The district court issued a thorough and well-reasoned
order articulating its basis for denying one of the evidentiary
objections, the prosecutorial-misconduct claim, and the jury-
instructions claim, see Rosenthal I, 266 F. Supp. 2d at 1079-
82, 1085 n.5, and ruled on the other evidentiary issue and the
Franks hearing issue orally. We agree with the district court’s
written and oral analysis of those issues and adopt its reason-
ing in whole. However, we reverse the district court on the
jury-misconduct claim.

  We independently review the question regarding immunity
under 21 U.S.C. § 885(d) to underscore our holding that the
provision does not apply to individuals, such as Rosenthal,
who are involved with medical-cannabis dispensaries.

  Finally, we dismiss as moot the government’s cross-appeal
challenging the length of the sentence.

                              IV

  [1] Rosenthal claims that he is immune from prosecution
under 21 U.S.C. § 885(d). We review de novo a district
court’s decision to dismiss an indictment based on an inter-
pretation of a federal statute. United States v. Marks, 379 F.3d
1114, 1116 (9th Cir. 2004), cert. denied, 543 U.S. 1170
(2005).

  21 U.S.C. § 885(d) states, in full:

    Except as provided in sections 2234 and 2235 of
    Title 18 [relating to illegal procurement and execu-
    tion of search warrants], no civil or criminal liability
    shall be imposed by virtue of this subchapter upon
    any duly authorized Federal officer lawfully engaged
    in the enforcement of this subchapter, or upon any
    duly authorized officer of any State, territory, politi-
                  UNITED STATES v. ROSENTHAL                4755
    cal subdivision thereof, the District of Columbia, or
    any possession of the United States, who shall be
    lawfully engaged in the enforcement of any law or
    municipal ordinance relating to controlled sub-
    stances.

Rosenthal argues that he was “lawfully engaged in the
enforcement” of the Oakland Ordinance by ensuring legal dis-
tribution of marijuana to seriously ill Californians. Moreover,
he notes that Oakland officials encouraged him to participate
in the distribution of medical marijuana, deputized him to per-
form that function, and promised, in writing, his immunity
from liability. For these reasons, Rosenthal claims he was a
“duly authorized officer” of the City of Oakland and immu-
nized by § 885(d).

   [2] Although the City of Oakland purported to authorize
Rosenthal to manufacture marijuana, he was not “duly autho-
rized” to do so, as state law does not allow the manufacturing
of marijuana by individuals other than the patient or his pri-
mary caregivers. See People ex rel. Lungren v. Peron, 70 Cal.
Rptr. 2d 20, 31-32 (1997). Consequently, Rosenthal was not
a “duly authorized officer” within the meaning of § 885(d), as
Oakland’s designation conflicted with state law. Accord State
v. Kama, 178 Or. App. 561(Or. Ct. App. 2002) (affirming trial
court’s finding that § 885(d) immunized Portland police offi-
cers from federal prosecution under 21 U.S.C. § 841(a)).

   [3] We further agree with the district court that cultivating
marijuana for medical use does not constitute “enforcement”
within the meaning of § 885(d). See Rosenthal I, 266 F. Supp.
2d at 1078. As the district court noted, “enforcement” means
“to compel compliance with the law . . . . At best, Rosenthal
was implementing or facilitating the purpose of the statute; he
was not compelling anyone to do or not to do anything.” Id.
Kama is not inconsistent with such a theory. In that case, the
state law mandated the return of marijuana to the individual
from whom the marijuana had been seized, and therefore the
4756              UNITED STATES v. ROSENTHAL
officers in question were “enforcing” the state law that
required them to deliver the marijuana to that individual
because he had a state-law right to its return. 178 Or. App. at
564-65. Here, in contrast, the state law does not give any per-
son a right to obtain medical marijuana from any particular
source, and the Oakland Ordinance does not mandate that
Rosenthal manufacture marijuana.

   We also agree with the district court’s conclusion that
Rosenthal’s interpretation of the immunity provision contra-
dicts the purpose of the CSA. Rosenthal I, 266 F. Supp. 2d at
1078-79. We note, as well, Rosenthal and the OCBC’s inti-
mate knowledge of the district court’s previous orders, which
rejected any claim that cannabis dispensaries were immune
from federal anti-drug laws. See supra Section I.B.

  [4] In conclusion, we reject the premise that an ordinance
such as the one Oakland enacted can shield a defendant from
prosecution for violation of federal drug laws. Rosenthal can-
not avail himself of the immunity provision of § 885(d).

                               V

   Rosenthal next contends that the court erred in refusing to
grant a new trial after it became aware that one of the jurors
(to whom we will refer as “Juror A”) sought advice from an
attorney on the eve of rendering a verdict. The district court,
upon conducting a hearing into the matter, concluded that
Rosenthal failed to demonstrate prejudice and denied the
motion for a new trial. We find that the district court applied
an overly burdensome standard of proof and that, under the
appropriate standard of review, prejudice is evident.

                               A

   Denial of a motion for a mistrial based on juror misconduct
is reviewed for abuse of discretion. United States v. Mills, 280
F.3d 915, 921 (9th Cir. 2002). Although this is an “extremely
                     UNITED STATES v. ROSENTHAL                        4757
deferential standard,” see United States v. Martinez-Martinez,
369 F.3d 1076, 1081-82 (9th Cir.), cert. denied, 543 U.S.
1013 (2004), the scenario changes where, as here, we consider
whether the district court applied the appropriate legal stan-
dard to guide its prejudice determination. See Suzy’s Zoo v.
Comm’r, 273 F.3d 875, 878 (9th Cir. 2001) (stating that “[a]
mixed question of law and fact exists when primary facts are
undisputed and ulitmate inferences and legal consequences
are in dispute”). Because we review a question of law, we
apply de novo review.

                                     B

   [5] Our juror-misconduct precedents “distinguish between
introduction of ‘extraneous evidence’ to the jury, and ex parte
contacts with a juror that do not include the imparting of any
information that might bear on the case.” Sea Hawk Seafoods,
Inc. v. Alyeska Pipeline Serv. Co., 206 F.3d 900, 906 (9th Cir.
2000). Extraneous-evidence cases involve not only the intro-
duction of “evidence” per se but the “submission of ‘extrane-
ous information’ (e.g., a file or dictionary) to the jury.” United
States v. Madrid, 842 F.2d 1090, 1093 (9th Cir. 1988). Ex
parte contacts, by contrast, generally do “not pertain to ‘any
fact in controversy or any law applicable to the case.’ ” Id.
(citing Rushen v. Spain, 464 U.S. 114, 121 (1983) (per
curiam)).

  Where ex parte communication is involved, the district
court, upon finding a reasonable possibility of prejudice, must
hold a fair hearing. See Madrid, 842 F.2d at 1094. At the
hearing, the defendant generally must demonstrate “actual
prejudice,” without which a new trial is not warranted.5 Id. at
  5
   In Sea Hawk Seafoods, we noted an exception in cases of inherently
coercive ex parte contact. See 206 F.3d at 906 (“[a]n ex parte remark may
in some circumstances merit a rebuttable presumption of prejudice
because of its inherently coercive effect, as where a judge instructs a juror
ex parte regarding the verdict . . . .”).
4758              UNITED STATES v. ROSENTHAL
1093; see also Sea Hawk Seafoods, 206 F.3d at 906 (noting
that, where ex parte contacts are involved, the defendant will
receive a new trial only if the court finds “actual prejudice”
to the defendant).

   [6] Extraneous-information cases, by contrast, call for more
searching review; we grant a new trial if “there is a reasonable
possibility that the material could have affected the verdict.”
Id. Unlike ex parte cases, we generally place the burden “on
the party opposing a new trial to demonstrate the absence of
prejudice.” Id. (emphasis added). Although the presence of
extrinsic material does not always require a new trial, com-
pare United States v. Bagley, 641 F.2d 1235, 1241 (9th Cir.
1981) (holding that extrinsic material regarding witness’s
immunity placed before jury was not prejudicial), with United
States v. Vasquez, 597 F.2d 192, 193-94 (9th Cir. 1979) (hold-
ing that file containing inadmissible extrinsic material left in
jury room for four hours was prejudicial), we carefully review
the circumstances and nature of the material to ensure that
jurors deliberate without undue outside pressure or influence.

                               C

   The district court determined that because the attorney-
friend “was not asked about and did not comment upon any
of the facts in the case nor opine on the applicable substantive
law,” this case involved ex parte contact. Rosenthal I, 266 F.
Supp. 2d at 1088-89. As an ex parte case, the district court
required that Rosenthal demonstrate “actual prejudice” to
secure a new trial. Id. at 1089.

   Unlike the district court, we see the conversation between
Juror A and legal counsel as involving extraneous informa-
tion, not ex parte contact. Moreover, we find that the govern-
ment has failed to demonstrate that there is no “reasonable
possibility” of prejudice.

  Juror A’s declaration supporting Rosenthal’s motion for a
new trial states that she felt “frustrated and confused” that
                     UNITED STATES v. ROSENTHAL                      4759
there had not been evidence that Rosenthal was involved in
growing medical marijuana, given the judge’s question con-
cerning medical marijuana during voir dire. She was “trou-
bled” that although she knew the case was about medical
marijuana, the judge instructed the jurors to decide the case
according to “federal law” and only on the “evidence that had
been presented in court.” Despite that instruction, she
expressed “confusion about whether we really had to only
consider the federal law.”

   Juror A believed that the district court’s instruction not to
discuss the case with anyone would not rule out a conversa-
tion “about a point of law”; accordingly, she phoned up an
attorney-friend to ask “if [she] had to follow the Judge’s
instructions, or if [she] had any leeway at all for independent
thought.” The attorney-friend responded that Juror A “defi-
nitely did have to following [sic] the Judge’s instructions, and
that there was absolutely nothing else [she] could do.” When
Juror A pressed the attorney, asking how there could ever be
hung juries, she was told “that could only happen if the Judge
gives the jury some leeway in his instructions.” The attorney
“then said [Juror A] could get into trouble if [she] tried to do
something outside those instructions.”

   Juror A discussed the matter with another juror, who shared
her own confusion with Juror A “whether a jury really has to
reach a verdict solely based on the law.” After the conversa-
tion with the attorney-friend, Juror A informed this second
juror that they had to follow the judge’s instructions.6

                                    D

   [7] We see the communication between Juror A and the
  6
    During the district court’s evidentiary hearing into prejudice, Juror A
refused to testify on Fifth Amendment grounds. The testimony of both
jurors, with the government’s consent, was provided by way of declara-
tions.
4760                 UNITED STATES v. ROSENTHAL
attorney-friend as raising an instance of extraneous evidence,
not ex parte contact. The circumstances involve the “submis-
sion of ‘extraneous information’ ” regarding the “law applica-
ble to the case.” Madrid, 842 F.2d at 1093 (emphasis added)
(second set of internal quotation marks omitted). The commu-
nication, tantamount to a substantive legal discussion, is akin
to the definition of “intent” or the distinctions between vari-
ous degrees of murder. This case thus triggers an inquiry into
whether there is a “reasonable possibility” that the extraneous
information affected the verdict. On that question, we hold
that, here, the communication was an improper influence
upon Juror A’s decision to acquit or convict.

   [8] Jurors cannot fairly determine the outcome of a case if
they believe they will face “trouble” for a conclusion they
reach as jurors. The threat of punishment works a coercive
influence on the jury’s independence, and a juror who genu-
inely fears retribution might change his or her determination
of the issue for fear of being punished.7 Not only is there a
“reasonable possibility” of prejudice, but the government has
not succeeded in rebutting the presumption that a new trial is
warranted. Accordingly, we reverse the district court and
order a new trial.

                                    VI

   Because we reverse the district court and order a new trial,
we need not address the government’s cross-appeal regarding
the district court’s imposition of a one-day sentence.8
  7
     Although we understand the district court’s concern that it not legiti-
mate or contribute to any effort by a juror to engage in nullification, we
do not think the court was ever in a position to do so since the evidentiary
hearing involved juror misconduct, which is the focus of concern here.
   8
     We note that, in the wake of the Supreme Court’s holding that we
apply a “reasonableness” review to sentencing decisions, see United States
v. Booker, 543 U.S. 220, 261 (2005), we would not be inclined to disturb
the court’s reasoned analysis underlying its sentencing determination.
                 UNITED STATES v. ROSENTHAL             4761
                            VII

   We reverse this case for a new trial due to juror miscon-
duct. We also hold that Rosenthal may not invoke the immu-
nity provision of 21 U.S.C. § 885(d). Finally, we dismiss as
moot the government’s appeal of the district court’s sentenc-
ing determination.

  REVERSED AND REMANDED.
