                              In the

    United States Court of Appeals
                For the Seventh Circuit
No. 16-3050

LEEANN BROCK-MILLER,
                                             Petitioner-Appellant,

                                v.


UNITED STATES OF AMERICA,
                                             Respondent-Appellee.

        Appeal from the United States District Court for the
        Southern District of Indiana, Indianapolis Division.
      No. 1:15-cv-01646-SEB-TAB— Sarah Evans Barker, Judge.


     ARGUED JANUARY 5, 2018 — DECIDED APRIL 3, 2018


   Before KANNE, ROVNER, and HAMILTON, Circuit Judges.

   ROVNER, Circuit Judge. LeeAnn Brock-Miller pled guilty,
pursuant to a plea agreement, to one count of conspiracy to
possess with intent to distribute heroin. She received the
agreed-upon sentence of ten years’ imprisonment and eight
years of supervised release. She then brought a timely motion
under 28 U.S.C. § 2255 to challenge her conviction, asserting
ineffective assistance of counsel during plea negotiations. The
2                                                      No. 16-3050

district court declined to hold a hearing, concluded that
counsel’s performance was not deficient and denied the
motion. We reverse and remand for a hearing on Brock-
Miller’s section 2255 motion.
                                   I.
    Brock-Miller was one of forty defendants charged with
various drug crimes in a twenty-six count indictment. Brock-
Miller was charged only in Count Six of the August 2012
indictment, with conspiracy to possess with intent to distribute
more than one kilogram of heroin in violation of
21 U.S.C. §§ 841(a)(1), 841(b)(1)(A)(i) and 846. According to the
indictment, the conspiracy was led by Oscar Perez and Justin
Addler, inmates in the Indiana Department of Corrections who
used illicit cell phones to oversee the acquisition of large
amounts of heroin from a source in Chicago and then facilitate
the distribution of that heroin into southern Indiana via
couriers. The conspiracy began in approximately June 2011 and
continued through August 2012. In the twenty-eight paragraph
“Overt Acts” section of Count Six, Brock-Miller1 is mentioned
just once, in paragraph twenty-seven:
     On or about July 13, 2012, after a series of telephone
     calls with JUSTIN ADDLER, BRIAN MOORE,
     LEEANN BROCK, and JOSHUA MILLER were in
     possession of $6,000 of JUSTIN ADDLER’S money,
     traveling on I-65 to Chicago to obtain a large quan-
     tity of heroin. During the trip, MILLER noticed law


1
  Brock-Miller was indicted under the name LeeAnn Brock, but proceeds
in this action under her married name, Brock-Miller.
No. 16-3050                                                   3

     enforcement agents conducting surveillance and
     began driving erratically in an attempt to avoid
     detection. MOORE subsequently threw the $6,000
     out the window of the vehicle.
    At the going rate of $110 per gram, $6,000 would have
purchased approximately fifty-four grams of heroin. Miller
and another man subsequently recovered the $6,000. As Brock-
Miller later told the sentencing judge, this car trip was an
isolated incident, where she agreed to give the others a ride in
exchange for one gram of heroin for herself. Brock-Miller had
an extensive criminal history that corroborated her claim that
she did not sell drugs but was an addict who simply bought
drugs for personal consumption.
    More than a year after the grand jury returned the indict-
ment charging Brock-Miller in Count Six, the government filed
an information under 21 U.S.C. § 851(a) indicating that it
intended to seek an enhanced penalty that is applicable to
persons who commit a drug offense after a prior conviction for
a felony drug offense has become final. See also 21 U.S.C.
§§ 841(b)(1)(A) and (B) (authorizing recidivist enhancements).
For Brock-Miller, this meant that the statutory minimum
sentence for the charged drug quantity rose from ten years to
twenty years, with the potential maximum remaining at life
imprisonment. 21 U.S.C. § 841(b)(1)(A). The prior felony drug
offense cited by the government was a 2008 Indiana conviction
for “Unlawful Possession of Syringes or Needles,” which the
4                                                         No. 16-3050

government considered a qualifying felony drug offense under
21 U.S.C. § 802(44).2
   Brock-Miller had in fact been convicted in 2008 for posses-
sion of syringes in violation of Indiana Code § 16-42-19-18
(2007). At that time, the Indiana law provided:
      A person may not possess or have under control
      with intent to violate this chapter a hypodermic
      syringe or needle or an instrument adapted for the
      use of a legend drug by injection in a human being.
The term “legend drug” referred to prescription drugs, see
infra, and did not include controlled substances such as heroin.
Brock-Miller’s conviction under the 2007 version of the statute
was later vacated, as we will discuss below, because the
substance she was charged with injecting was heroin, which is
not a legend drug and thus her conduct was not covered by the
statute. The statute was later amended to include both legend
drugs and controlled substances such as heroin, a change in the
law that does not affect the outcome here but that helps explain
an error in the district court’s analysis in this case.
    In any event, Brock-Miller’s counsel objected to the section
851 information by contending that Brock-Miller did not have
a conviction under Indiana Code § 35-48-4-8.3, which criminal-
izes the possession of drug paraphernalia. Counsel argued that
first time offenses under the paraphernalia statute are consid-
ered misdemeanors and so the conviction could not be consid-


2
  Brock-Miller possessed the syringes in August 2007, and pled guilty in
2008. Thus, the 2007 version of the statute controlled. The statute was
amended in 2015.
No. 16-3050                                                                5

ered a felony drug offense for the purpose of enhancing the
sentence under sections 841(b) and 851.3 This was a frivolous
and misdirected objection, though, for at least two reasons.
First, Brock-Miller had never been convicted of possessing
drug paraphernalia under section 35-48-4-8.3. And second, the
government had not asserted a conviction under section 35-48-
4-8.3 for possession of paraphernalia as the basis for the
recidivist enhancement; it had cited Brock-Miller’s conviction
for Unlawful Possession of Syringes or Needles. Although the
government did not specify the Indiana statute under which
Brock-Miller had been convicted, the section 851 information
listed the case number, date of conviction and county in which
she was convicted. State records for the conviction indicate that
Brock-Miller was charged under Indiana Code § 16-42-19-18,
not § 35-48-4-8.3.
    A check of Brock-Miller’s record of conviction would have
revealed the correct statutory cite, and a proper analysis would
have confirmed that Brock-Miller had a meritorious objection
to the recidivist enhancement, as we will discuss below. But
her lawyer never raised a proper objection to the section 851
information and the district court never ruled on the frivolous
objection that was filed. Brock-Miller, believing that she faced
a mandatory minimum sentence of twenty years, pled guilty
to conspiracy to possess with intent to distribute more than 100


3
  Sections 841(b)(1)(A) and (b)(1)(B) authorize the enhanced recidivist
sentences at issue in this case, the former applying to larger quantities of
heroin and the latter to smaller quantities. Section 851 provides the
procedure for establishing that the enhancements apply. These statutes
collectively are the basis for the recidivist enhancement at issue here.
6                                                    No. 16-3050

grams of heroin, a smaller amount than was initially charged.
She agreed to accept a sentence of ten years’ imprisonment and
eight years of supervised release, and gave up her right to file
a direct appeal or a collateral challenge to her conviction and
sentence.
     At the change of plea hearing, there was considerable
confusion regarding the sentencing range. The court first stated
that the maximum sentence for Count Six was forty years.
Counsel for the government interposed that the correct range
was “ten to life.” The court noted that Brock-Miller’s petition
to enter a plea of guilty showed a range of five to forty years.
The government then agreed that five to forty years was the
correct range and the court then repeated to Brock-Miller that
the sentencing range was five to forty years. After reviewing
the plea agreement itself, the court again asked for clarification
because that document showed a sentencing range of ten years
to life. Brock-Miller’s appointed counsel told the court that her
client pled guilty to a lesser amount of heroin than was initially
charged and so the range for the lesser included count to which
she was pleading was five to forty years. Government counsel
agreed again that the sentencing range for the charge to which
Brock-Miller was entering a plea was five to forty years. The
court then told Brock-Miller that her sentencing range would
have been ten years to life for the crime initially charged but
that her plea agreement reduced the range to five to forty
years. That was incorrect. For the kilogram quantity of heroin
initially charged, the sentencing range was ten years to life
without the recidivist enhancement and twenty years to life
with the enhancement. For the reduced amount of heroin to
which Brock-Miller pled guilty, the sentencing range was five
No. 16-3050                                                         7

to forty years without the recidivist enhancement and ten years
to life when the enhancement was included. At sentencing, the
court noted for the first time that the plea agreement provided
for a binding sentence of ten years, and that the correct
statutory range for the lesser amount of heroin, together with
the enhancement under sections 841(b) and 851, was ten years
to life.4 The court also gave Brock-Miller an eight-year term of
supervised release to follow the ten-year term of imprison-
ment.
    After sentencing, Brock-Miller filed and then quickly
withdrew a timely pro se notice of appeal. She then filed a
timely pro se motion for collateral relief under 28 U.S.C. § 2255.
She alleged ineffective assistance of counsel in violation of the
Sixth Amendment, and a denial of due process in violation of
the Fifth Amendment. She dropped the latter claim on appeal
and so we focus on her ineffective assistance claim only. In that
claim, she alleged that her appointed counsel filed a frivolous
objection to the government’s section 851 filing, and made
erroneous factual assertions in the objection. Brock-Miller
asserted that she informed her lawyer of the error, but counsel
failed to investigate or correct the error, and failed to seek a
hearing on the objection. Brock-Miller also alleged that her
lawyer inappropriately advised her to enter into a plea
agreement that allowed her to be sentenced as a recidivist,


4
  The guidelines range was 92 to 115 months of imprisonment, a range
which Brock-Miller asserts would now be 77 to 96 months based on the
retroactive Amendment 782 to the sentencing guidelines. The mandatory
minimum of ten years (120 months) for the crime to which Brock-Miller
pled guilty made the guidelines calculation largely irrelevant.
8                                                  No. 16-3050

without any proper objection to that enhancement and without
seeking any determination by the court regarding whether the
recidivist provision actually applied to her. Finally, Brock-
Miller contended that her lawyer made the same error regard-
ing the sentencing enhancement in objecting to the pre-
sentence investigation report (“PSR”). Because the objections
as filed were frivolous, Brock-Miller contended that the court
overlooked the objections and failed to hold the necessary
hearing to rule on the objections. Brock-Miller sought new
counsel and a new sentencing hearing that included a ruling
on whether the recidivist provision applied to her, as well as
any other available relief.
    The district court denied Brock-Miller’s section 2255
motion. The court first correctly noted that Brock-Miller’s plea
agreement included a waiver of the right to seek collateral
relief, but that such waivers would not be upheld and enforced
if, among other things, the defendant claimed ineffective
assistance of counsel in relation to the negotiation of the plea
agreement. Brock-Miller claimed that her conviction for
unlawful possession of syringes was not a felony drug offense
for purposes of the recidivist enhancement, the court noted. In
analyzing Brock-Miller’s claim, the court examined Indiana
Code § 16-42-19-18, the correct statute for her predicate
conviction. Unfortunately, though, the court cited the later-
revised version which prohibits possession of “a hypodermic
syringe or needle or an instrument adapted for the use of a
controlled substance or legend drug by injection in a human
being.” Indiana Code 16-42-19-18 (2015) (emphasis added). The
version in effect at the time of Brock-Miller’s conviction made
no mention of controlled substances. Unaware of the interven-
No. 16-3050                                                   9

ing amendment to the law, the district court held that a
conviction under that statute would meet the definition of a
felony drug offense under 21 U.S.C. § 802(44), which would
then fall within the scope of the recidivist enhancement. Based
on that analysis of the wrong version of the Indiana law, the
court concluded that counsel’s performance was not deficient,
that Brock-Miller had knowingly and voluntarily entered into
her plea agreement, and that the court would therefore uphold
the waiver provision in the plea agreement. The court denied
the motion for relief under section 2255 and also denied a
certificate of appealability. But this court found that Brock-
Miller made a substantial showing that her guilty plea was not
knowing and voluntary and that she did not receive effective
assistance of counsel. We therefore granted a certificate of
appealability and appointed counsel to represent Brock-Miller
on appeal.
                                II.
    Brock-Miller raises two primary issues on appeal. First, she
contends that her conviction under the 2007 version of the
Indiana Legend Drug Act does not qualify as a felony drug
offense under 21 U.S.C. § 802(44) because the Indiana law at
the time of her conviction regulated only prescription drugs
and thus did not prohibit or restrict conduct related to a
controlled substance. The district court erred both factually
and legally, she asserts, in concluding to the contrary. Second,
she argues that her appointed lawyer was ineffective in plea
negotiations when she did not properly object to the section
851 information and instead coerced Brock-Miller into entering
a binding ten-year sentencing agreement to avoid risking an
improperly-enhanced recidivist sentence after trial. Although
10                                                    No. 16-3050

she maintains that she has established both deficient perfor-
mance and prejudice from counsel’s errors, and that she is
entitled to the relief of withdrawing her guilty plea, in the
alternative Brock-Miller requests an evidentiary hearing.
                                  A.
    Section 2255 allows a prisoner in federal custody to move
for relief on “the ground that the sentence was imposed in
violation of the Constitution or laws of the United States.” 28
U.S.C. § 2255(a); Sawyer v. United States, 874 F.3d 276, 278 (7th
Cir. 2017). The district court in which the motion is filed is
required to hold a prompt hearing on the matter unless “the
motion and the files and records of the case conclusively show
that the prisoner is entitled to no relief[.]” 28 U.S.C. § 2255(b).
When a district court denies a motion for relief under section
2255, we review the court’s legal conclusions de novo and
factual findings for clear error. Sorich v. United States, 709 F.3d
670, 673 (7th Cir. 2013). We review for abuse of discretion the
court’s decision not to hold an evidentiary hearing. Martin v.
United States, 789 F.3d 703, 706 (7th Cir. 2015). A decision that
rests on an error of law is always an abuse of discretion. United
States v. Simon, 727 F.3d 682, 696 (7th Cir. 2013).
                                  1.
   Brock-Miller is correct that the district court erred when it
concluded that her prior conviction under Indiana Code §16-
42-19-18 was a felony drug offense under 21 U.S.C. § 802(44)
and she was therefore eligible for a recidivist enhancement.
Brock-Miller initially was charged with possessing more than
a kilogram of heroin but later pled guilty to possessing 100
grams or more. Section 841(b)(1)(A) sets the penalty for a
No. 16-3050                                                    11

kilogram quantity of heroin at ten years to life; section
841(b)(1)(B) sets the penalty for more than 100 grams at five to
forty years. For both quantities, section 841(b) also proscribes
a higher, recidivist sentence if “any person commits such a
violation after a prior conviction for a felony drug offense has
become final[.]” 21 U.S.C. §§ 841(b)(1)(A) and (B) (emphasis
added). For the kilogram quantity, the mandatory minimum
sentence increases from ten years to twenty and the maximum
remains life. For the 100 gram quantity, the mandatory
minimum sentence increases from five years to ten years and
the maximum increases from forty years to life. Section 851
proscribes the procedure for establishing a prior conviction
that qualifies, beginning with the government filing an
information describing the prior conviction on which the
enhancement will rest.
     Although the district court correctly identified Indiana
Code § 16-42-19-18 as the statute of conviction for Brock-
Miller’s prior offense, the court cited a later version of the
statute when analyzing her claim. The first version, as we
noted above, applied to the use of syringes only with legend
drugs. The later version, on which the district court relied,
criminalized the use of syringes with legend drugs or con-
trolled substances. Under either version of the law, the term
“legend drugs” was defined under Indiana law with reference
to prescription drugs, not controlled substances such as heroin.
See Indiana Code § 16-18-2-199 (1993). That section of the
Indiana Code, enacted in 1993 and still valid at the time of
Brock-Miller’s offense in 2007, defined “legend drug” as a drug
subject to 21 U.S.C. § 353(b)(1) or a drug listed in the prescrip-
tion drug product lists published by the United States Depart-
12                                                          No. 16-3050

ment of Health and Human Services.5 Section 353(b)(1)
provides that certain drugs “intended for use by man” require
prescriptions by a physician before being dispensed. Thus, the
term “legend drugs” under Indiana law in 2007 was limited to
prescription drugs. Indeed, the government concedes this
point. See Brief for the United States, at 18 (“And, in fact, she
does appear to be right on this score” that the statute “includes
prescription drugs that fall outside the federal definition of
felony drug offenses.”).
    We turn to the federal statute to determine if Brock-Miller’s
conviction under the correct version of the Indiana law
qualifies as a “felony drug offense” for the purposes of a
recidivist enhancement. The term “felony drug offense” as
used in section 841(b) is defined in 21 U.S.C. § 802(44):
      The term “felony drug offense” means an offense
      that is punishable by imprisonment for more than
      one year under any law of the United States or of a
      State or foreign country that prohibits or restricts




5
  The term “drug” itself is defined in another part of the Indiana statute.
See Indiana Code § 16-42-19-2. The statute defines “drug” very broadly to
include, among other things, substances listed in the United States
Pharmacopeia and the National Formulary; articles or substances in-
tended for use in the diagnosis, cure, mitigation, treatment, or prevention
of disease in human beings or other animals; articles other than food
intended to affect the structure or any function of the body of human
beings or other animals; components of those first three categories; and
“devices.” The term “legend drug” is a subset of this broader category of
drugs.
No. 16-3050                                                      13

     conduct relating to narcotic drugs, marihuana,
     anabolic steroids, or depressant or stimulant sub-
     stances.
See also Burgess v. United States, 553 U.S. 124, 129 (2008) (section
802(44) provides the exclusive definition of “felony drug
offense,” including for the purpose of section 841(b) enhance-
ments). Each category of covered drugs is, in turn, also defined
by statute. See 21 U.S.C. § 802(17) (defining narcotic drugs); 21
U.S.C. § 802(16) (defining marihuana); 21 U.S.C. § 802(41)(A)
(defining anabolic steroid); and 21 U.S.C. § 802(9) (defining
depressant or stimulant substance). There is little to no overlap
between the controlled substances listed in the federal defini-
tion of “felony drug offense” and the prescription “legend
drugs” regulated by the Indiana law. No one disputes that
heroin is not a legend drug. Brock-Miller therefore was not
convicted “under any law of … a State … that prohibits or
restricts conduct relating to narcotic drugs, marihuana,
anabolic steroids, or depressant or stimulant substances.” 21
U.S.C. § 802(44). And so Brock-Miller’s conviction under
section 16-42-19-18 was not a felony drug offense and would
not have exposed her to any recidivist sentencing enhance-
ment.
                                  2.
    Brock-Miller framed her argument in part by using the
language of the categorical approach established in Taylor v.
United States, 495 U.S. 575 (1990), and in part by employing a
straight-forward application of the definition of “felony drug
offense” provided by section 802(44). The government, in its
briefing, also blends those approaches and seems to assume
14                                                            No. 16-3050

that both the section 802(44) definition and the categorical
approach must be employed to determine whether a convic-
tion under state law meets the federal definition of “felony
drug offense.” The distinction makes no difference to the
outcome here.6 Whether we use the categorical approach


6
  Under Taylor’s categorical approach, courts deciding whether a prior
conviction qualifies as a predicate offense under the Armed Career
Criminal Act (“ACCA”) look only to the statutory elements of the prior
offense, and not to the particular facts underlying the conviction. “If the
relevant statute has the same elements as the ‘generic’ ACCA crime, then
the prior conviction can serve as an ACCA predicate; so too if the statute
defines the crime more narrowly, because anyone convicted under that
law is ‘necessarily … guilty of all the [generic crime's] elements.’ … But if
the statute sweeps more broadly than the generic crime, a conviction
under that law cannot count as an ACCA predicate, even if the
defendant actually committed the offense in its generic form. The key,
we emphasized, is elements, not facts.” Descamps v. United States, 570 U.S.
254, 260–61 (2013). The Indiana statute at issue here regulates prescrip-
tion drugs, which broadly includes many substances that bear no relation
to the federal “felony drug offense” exclusively defined in section
802(44). Because the Indiana statute encompasses much more conduct
than the “felony drug offense” defined in section 802(44), Brock-Miller’s
Indiana conviction may not serve as a predicate offense for a recidivist
enhancement, even if we were to apply the categorical approach.
Moncrieffe v. Holder, 569 U.S. 184, 190–91 (2013) (“Because we examine
what the state conviction necessarily involved, not the facts underlying
the case, we must presume that the conviction ‘rested upon [nothing]
more than the least of th[e] acts’ criminalized, and then determine
whether even those acts are encompassed by the generic federal of-
fense.”) (quoting Johnson v. United States, 559 U.S. 133, 137 (2010)). Even if
there were overlap between legend drugs and the drugs listed in section
802(44), we would have to assume under the categorical approach that
Brock-Miller’s conviction rested on prescription drugs and not the
                                                                (continued...)
No. 16-3050                                                              15

defined in Taylor or simply compare the definition provided in
section 802(44) with the law under which the offense was
charged in state court, the result is the same: Brock-Miller’s
conviction under Indiana law does not qualify as a felony drug
offense.
    As far as we can tell, our circuit has not expressly employed
the Taylor categorical approach in resolving whether a state
conviction is a “felony drug offense” under section 802(44),
instead simply comparing the straight-forward federal
definition to the state statute of conviction. See e.g., United
States v. Elder, 840 F.3d 455, 461–62 (7th Cir. 2016) (finding that
an Arizona conviction for possession of drug paraphernalia
was not a felony drug offense within the meaning of section
841 because the statute under which the defendant was
convicted capped the sentence at one year, contrary to the
definition of “felony drug offense” provided by section 802(44),
which requires the qualifying conviction to be punishable by
a term of imprisonment of more than one year). See also United
States v. Brown, 598 F.3d 1013, 1015–18 (8th Cir. 2010) (conclud-
ing that Iowa convictions for delivery of simulated controlled
substances were not felony drug offenses by analyzing the


6
  (...continued)
section 802(44) controlled substances. In any case, as we discuss below,
the State of Indiana does not consider heroin to be a legend drug. See e.g.
Bookwalter v. State, 22 N.E.3d 735, 740–41 (Ind. Ct. App. 2014). Finally,
although the government urges us to apply the modified categorical
approach of Shepard v. United States, 544 U.S. 13 (2005), to save its argu-
ment, that case does not apply here because the 2007 version of the
Indiana statute was not divisible. See United States v. Yang, 799 F.3d 750,
753 (7th Cir. 2015).
16                                                            No. 16-3050

meaning of the phrase “relating to” in section 802(44) in
connection with section 801(2)’s reference to the regulation of
controlled substances); United States v. Grayson, 731 F.3d 605,
606–08 (6th Cir. 2013) (determining, without mention of the
categorical approach, that a Michigan conviction for maintain-
ing a drug house qualifies as a felony drug offense because the
crime is punishable by up to two years’ imprisonment and
because the controlled substances referenced in the Michigan
statute are congruent with those listed in section 802(44));
United States v. Soto, 8 Fed. Appx. 535, 541 (6th Cir. 2001)
(noting that the Sixth Circuit “does not employ a categorical
approach to determining whether a prior conviction constitutes
a ‘felony drug offense’ for purposes of section 841(b)(1)”). But
see United States v. Ocampo-Estrada, 873 F.3d 661, 667–69 (9th
Cir. 2017) (applying the categorical approach in deciding
whether a California conviction qualified as a “felony drug
offense”);7 United States v. Brown, 500 F.3d 48, 59 (1st Cir. 2007)


7
  Although Ocampo-Estrada used the categorical approach without
specifically addressing whether it was applicable, a week after that
decision was issued, an unpublished decision of the Ninth Circuit ap-
peared to take the position that the categorical approach might not apply
in this context:
         Though both parties argue that the categorical approach
         applies when determining whether a prior conviction is
         a “felony drug offense” under § 841, we have never held
         in a published opinion that it applies in this context.
         Though we need not reach the issue, we note that the
         categorical approach may be a poor fit for sentencing
         determinations under 21 U.S.C. § 851, which sets up a
         statutory, trial-like procedure for determining whether
                                                                (continued...)
No. 16-3050                                                                  17

(analyzing section 802(44) by eschewing an examination of the
particular facts of the putative predicate crime and instead
reading the term “felony drug offense” categorically under
Taylor and Shepard v. United States, 544 U.S. 13 (2005)); United
States v. Nelson, 484 F.3d 257, 261 n.3 (4th Cir. 2007) (applying
both the section 802(44) definition and Shepard in determining
whether a conviction under 18 U.S.C. § 924(c)(1) is a felony
drug offense for purposes of the recidivist enhancement);
United States v. Curry, 404 F.3d 316, 320 (5th Cir. 2005) (using
the statutory definition of felony drug offense along with
Shepard in determining whether a prior conviction fits the
recidivist enhancement provision). The Supreme Court has
characterized section 802(44) as providing the “exclusive
definition of ‘felony drug offense,’” which has the benefit of
bringing “a measure of uniformity to the application of
§ 841(b)(1)(A) by eliminating disparities based on divergent
state classifications of offenses.” Burgess, 553 U.S. at 134. We
reserve for another day the question of whether the Tay-
lor/Shepard categorical approach applies to the term “felony
drug offense” for the purpose of the recidivist enhancement.
Under either approach, Brock-Miller’s Indiana conviction was
not a felony drug offense. The district court erred when it
analyzed the wrong version of the Indiana law, which then led
the court to mistakenly conclude that Brock-Miller’s Indiana
conviction qualified as a felony drug offense.

7
  (...continued)
         the defendant has a prior conviction for a “felony drug
         offense.”
 United States v. Torres, 711 Fed. Appx. 829, — n.2 (9th Cir. 2017). As in
the instant case, the approach taken did not affect the outcome.
18                                                     No. 16-3050

                                   B.
     Brock-Miller’s section 2255 claims are founded on her Sixth
Amendment right to counsel, “a right that extends to the
plea-bargaining process.” Lafler v. Cooper, 566 U.S. 156, 162
(2012). In particular, during plea negotiations, defendants are
entitled to “the effective assistance of competent counsel.”
Lafler, 566 U.S. at 162 (quoting McMann v. Richardson, 397 U.S.
759, 771 (1970)). See also Missouri v. Frye, 566 U.S. 134, 141
(2012) (negotiation of a plea bargain is a critical phase of
litigation for purposes of the Sixth Amendment right to
effective assistance of counsel). We apply the familiar two-part
test under Strickland v. Washington, 466 U.S. 668 (1984), when
we evaluate challenges to guilty pleas based on ineffective
assistance of counsel. Lafler, 566 U.S. at 162–63; Hill v. Lockhart,
474 U.S. 52, 58 (1985). Under Strickland, a defendant must first
demonstrate that counsel’s performance was deficient. Second,
a “defendant must show that the deficient performance
prejudiced the defense.” Strickland, 466 U.S. at 687.
                                   1.
    Under the first part of the Strickland test, we consider
whether counsel’s representation fell below an objective
standard of reasonableness. Strickland, 466 U.S. at 687–88.
Brock-Miller contends that counsel’s performance was defi-
cient in several critical respects. First, counsel failed to investi-
gate Brock-Miller’s criminal record in Indiana to determine the
statute under which Brock-Miller had been charged with
possessing syringes. This led to counsel’s second error, filing
a frivolous objection to the government’s section 851 informa-
tion citing the wrong Indiana statute. Counsel then failed to
No. 16-3050                                                     19

seek a ruling on that objection, and instead grossly over-
estimated Brock-Miller’s sentencing exposure. Brock-Miller
contends that she was led to believe that she faced a manda-
tory minimum of twenty years, a minimum that never applied
to her, even considering the kilogram quantity of heroin
initially charged. That led to counsel advising Brock-Miller to
accept a plea deal that was really no deal at all. Had counsel
investigated Brock-Miller’s record in Indiana, she contends that
counsel would have realized that Brock-Miller had a meritori-
ous objection to the section 851 information and that her client
was not subject to an enhanced sentence for recidivists. Brock-
Miller asserts that competent counsel would have correctly
calculated her sentencing range, filed a meritorious objection
and demanded a ruling, and then either negotiated a better
deal or advised her to reject the government’s offer and go to
trial.
    In the plea bargaining context, a reasonably competent
lawyer must attempt to learn all of the relevant facts of the
case, make an estimate of the likely sentence, and communicate
the results of that analysis to the client before allowing the
client to plead guilty. Spiller v. United States, 855 F.3d 751, 755
(7th Cir. 2017); Gaylord v. United States, 829 F.3d 500, 506 (7th
Cir. 2016); Bethel v. United States, 458 F.3d 711, 717 (7th Cir.
2006). See also Moore v. Bryant, 348 F.3d 238, 241 (7th Cir. 2003)
(to demonstrate deficient performance in the context of a guilty
plea, a petitioner must demonstrate that his counsel's advice
regarding the plea was objectively unreasonable). Brock-
Miller’s counsel appears to have failed that standard on several
fronts.
20                                                    No. 16-3050

    Because the district court declined to hold a hearing on
Brock-Miller’s section 2255 motion, the record is not fully
developed on several important issues. From the limited
record of the plea proceedings, it appears that counsel first
failed to check Brock-Miller’s criminal record and discern the
relevant statute for the predicate conviction. Brock-Miller had
been convicted under Indiana Code § 16-42-19-18, but counsel
incorrectly cited Indiana Code § 35-48-4-8.3 as the basis for the
conviction. That threshold factual error may have led counsel
to erroneously conclude that Brock-Miller was subject to the
recidivist enhancement, which in turn may have caused
counsel to make significant errors in predicting the likely
sentence. A lawyer’s failure to learn the relevant facts and
make an estimate of the likely sentence constitutes deficient
performance. Moore, 348 F.3d at 242. See also Padilla v. Kentucky,
559 U.S. 356, 368–69 (2010) (advice to accept guilty plea which
led to deportation found deficient where the consequences of
the plea could easily be determined by reading the removal
statute, the deportation was mandatory, and the advice that a
guilty plea would not result in deportation was incorrect);
Bridgeman v. United States, 229 F.3d 589, 592 (7th Cir. 2000) (in
the plea context, inaccurate advice that resulted from the
attorney's failure to undertake a good-faith analysis of all of the
relevant facts and applicable legal principles establishes
deficient performance under Strickland).
   The errors asserted here are very similar to those alleged in
Gaylord v. United States, 829 F.3d 500 (7th Cir. 2016). In that
case, the defendant pled guilty to conspiracy to distribute
oxycodone and received an enhanced sentence under section
841(b)(1)(C), which applies when “death results” from the use
No. 16-3050                                                   21

of the charged substance. Gaylord distributed the drug to a
person who then passed it on to another person who ingested
it along with cocaine and subsequently died. Counsel failed to
alert Gaylord that postmortem and forensic pathology reports
did not support the conclusion that oxycodone was the but-for
cause of the death at issue. Counsel also failed to challenge the
application of the “death results” enhancement to Gaylord’s
sentence. Gaylord’s guidelines range would have been 210 to
262 months but the enhancement subjected him to the twenty
year mandatory minimum and the court sentenced Gaylord to
twenty years’ imprisonment. Gaylord subsequently challenged
his sentence with a section 2255 motion. Like Brock-Miller, his
plea agreement waived his rights to a direct appeal and any
collateral challenge. As with Brock-Miller, we recognized that
a defendant may overcome such waivers by demonstrating
that the plea agreement was the product of ineffective assis-
tance of counsel. 829 F.3d at 503–06.
    Gaylord argued that counsel was deficient for failing to
adequately investigate his case and failing to provide him with
the forensic and pathology reports so that he could make an
informed decision regarding whether to plead guilty. He also
contended that counsel was deficient for failing to challenge
the application of the “death results” enhancement to his
sentence. We agreed that, if proven, these alleged errors would
constitute deficient performance under Strickland. We found
that there was a substantial probability that the application of
the enhancement in Gaylord’s case was inconsistent with the
prevailing but-for standard of causation. The medical reports
provided no evidence that the drug Gaylord distributed
caused the subject death. Because Gaylord was not provided
22                                                  No. 16-3050

with a hearing on his claim, the record contained no evidence
regarding whether counsel was aware of the proper causation
standard, whether he had examined the medical reports, and
whether he had provided Gaylord with the information
necessary for a knowing and voluntary plea. In sum, we
concluded that Gaylord’s allegations supported his claim that
his counsel performed deficiently by failing to provide him
with the postmortem and forensic pathology reports and not
challenging the application of the “death results” enhancement
to his sentence. 829 F.3d at 506–08. We remanded for a hearing
so that Gaylord could prove his allegations.
    Brock-Miller’s circumstances are directly analogous.
Counsel’s apparent error in identifying the applicable Indiana
statute, the frivolous challenge under section 851, and the
failure to file a plainly meritorious objection could constitute
deficient performance if proved. See also Prou v. United States,
199 F.3d 37, 48 (1st Cir. 1999) (a failure to raise a clearly
meritorious objection to a section 851 information when
presenting it would have risked nothing amounts to constitu-
tionally deficient performance); Hinton v. Alabama, 134 S. Ct.
1081, 1089 (2014) (“An attorney’s ignorance of a point of law
that is fundamental to his case combined with his failure to
perform basic research on that point is a quintessential
example of unreasonable performance under Strickland.”).
Brock-Miller appears to have a strong case for section 2255
relief if these errors led to counsel failing to make an estimate
of the likely sentence, and instead grossly overestimating her
client’s sentencing exposure. Any resultant advice to Brock-
Miller to take the government’s plea offer may well have been
founded on deficient performance. Hurlow v. United States, 726
No. 16-3050                                                      23

F.3d 958, 967–68 (7th Cir. 2013) (“a plea, even one that complies
with Rule 11, cannot be ‘knowing and voluntary’ if it resulted
from ineffective assistance of counsel.”). On remand, if Brock-
Miller is able to prove deficient performance in the negotiation
of her plea agreement, the court should not hold her to the
waiver of her right to collaterally challenge the plea agreement
with a section 2255 motion. Hurlow, 726 F.3d at 966–67 (in
order to overcome an appeal waiver in a plea agreement, a
defendant must allege that he entered the plea agreement
based on advice of counsel that fell below constitutional
standards).
    Before we turn to the second part of the Strickland analysis,
we must address a few issues raised by the government on the
question of deficient performance. At various points in its
briefing, the government concedes that Brock-Miller’s attorney
made mistakes. See e.g. Brief for the United States, at 14
(“Brock-Miller offers a substantial argument that her lawyer
made a real mistake[.]”); at 18 (“And, in fact, she does appear
to be right on this score” that legend drugs are prescription
drugs that fall outside the federal definition under section
802(44)); at 18 (“To be sure, Brock-Miller’s initial objection [to
the section 851 information] was lacking.”). Nevertheless, the
government contends that counsel’s errors were not suffi-
ciently egregious to meet the Strickland standard for deficient
performance. The government characterizes Brock-Miller’s
argument as both “sophisticated” and “convoluted,” and in
any event beyond what is required by Strickland.
   We disagree. The alleged errors, if true, were contrary to
the well-settled Strickland standard for the plea bargaining
context. Spiller, 855 F.3d at 755; Gaylord, 829 F.3d at 506; Bethel,
24                                                         No. 16-3050

458 F.3d at 717. Brock-Miller asserts that counsel failed to learn
the relevant facts of the case when she failed to identify the
correct Indiana statute for the predicate conviction. She also
alleges that counsel then failed to examine that statute to
determine if it met the federal definition of felony drug offense.
That analysis would have required little more than reading the
Indiana statute and the provisions it cross-referenced, and
comparing them to the federal definition of felony drug
offense. Counsel would then have realized that heroin was not
a legend drug, triggering the filing of an appropriate and
meritorious objection. Competent counsel would not have then
advised her client to accept a plea that was based on an
unwarranted recidivist enhancement.
    The government counters that, at the time Brock-Miller was
charged, “Indiana courts had sustained convictions for
unlawful possession of a syringe in order to ingest heroin.”
Brief for the United States, at 21.8 The government cites Cherry
v. State, 971 N.E.2d 726 (Ind. Ct. App. 2012), in support of its

8
  We assume the government simply misspoke when it used the plural
“courts,” in that claim. Cherry is the only Indiana case cited in support
and it is the only case we were able to find in which a court sustained a
conviction under section 16-42-19-18 in connection with heroin. The
assumption made in Cherry is somewhat understandable in light of the
history of Indiana laws governing the possession of syringes. A version
of the statute in operation in 1972 appears to have covered possession of
a syringe “adapted for the use of narcotic drugs by injection in a human
being.” Cooper v. State, 357 N.E.2d 260, 264 (Ind. Ct. App. 1976). And
Indiana added controlled substances back into the mix in a 2015 amend-
ment. But a competent lawyer reading the 2007 version would have seen
that the statute applied only to legend drugs, which in turn encompassed
only prescription drugs.
No. 16-3050                                                      25

claim that “[b]y all outward appearances, her crime seemed to
fit the broad definition of felony drug offense.” It is true that an
Indiana court in Cherry sustained a conviction under Indiana
Code 16-42-19-18 for possessing a syringe in connection with
heroin. But the defendant in that case did not challenge
whether heroin was a legend drug and the court simply
assumed, without deciding, that heroin came within the
statute. No Indiana court faced or decided the question of
whether heroin was a legend drug until Bookwalter directly
confronted the issue in 2014 and concluded that “intent to
inject heroin is not fairly covered by the Legend Drug Act's
definition of the offense of possession of a syringe.” 22 N.E.3d
at 741. That decision was followed, of course, by Brock-Miller’s
own collateral challenge to her Indiana conviction which also
resulted in a finding that possessing a syringe in connection
with heroin is not covered by the statute. A lawyer reviewing
Cherry would have seen that the case did not decide or even
address the issue presented here. Reading statutes and
discerning their plain meaning is neither convoluted nor
sophisticated; it is what lawyers must do for their clients every
day. The Strickland standard requires more than an analysis of
“all outward appearances.” Brock-Miller has presented enough
evidence to warrant a hearing on deficient performance. At
that hearing, counsel will have an opportunity to respond to
Brock-Miller’s allegations and characterization of the events
leading to the plea deal. If the district court finds that counsel’s
performance was deficient, the court should set aside the
waiver of appeal and collateral challenge rights, and reach the
merits of Brock-Miller’s section 2255 claim.
                                  2.
26                                                    No. 16-3050

    In the context of a guilty plea, the second part of the
Strickland test:
     focuses on whether counsel’s constitutionally inef-
     fective performance affected the outcome of the plea
     process. In other words, in order to satisfy the
     “prejudice” requirement, the defendant must show
     that there is a reasonable probability that, but for
     counsel’s errors, he would not have pleaded guilty
     and would have insisted on going to trial.
Hill, 474 U.S. at 59. Hill set the standard for prejudice where the
defendant claimed “that ineffective assistance led to the
improvident acceptance of a guilty plea[.]” Lafler, 566 U.S. at
163 (quoting Hill, 474 U.S. at 59). In Lafler, the defendant
asserted that counsel’s deficient performance led to the
defendant rejecting a favorable plea and instead standing trial:
     In these circumstances a defendant must show that
     but for the ineffective advice of counsel there is a
     reasonable probability that the plea offer would
     have been presented to the court (i.e., that the defen-
     dant would have accepted the plea and the prosecu-
     tion would not have withdrawn it in light of inter-
     vening circumstances), that the court would have
     accepted its terms, and that the conviction or sen-
     tence, or both, under the offer’s terms would have
     been less severe than under the judgment and
     sentence that in fact were imposed.
Lafler, 566 U.S. at 164. In Frye, the defendant asserted that
counsel’s failure to convey the prosecutor’s favorable plea
offers to the defendant before the offers lapsed prejudiced him.
No. 16-3050                                                      27

That led to yet another formulation of the necessary prejudice
showing:
     In order to complete a showing of Strickland preju-
     dice, defendants who have shown a reasonable
     probability they would have accepted the earlier
     plea offer must also show that, if the prosecution
     had the discretion to cancel it or if the trial court had
     the discretion to refuse to accept it, there is a reason-
     able probability neither the prosecution nor the trial
     court would have prevented the offer from being
     accepted or implemented.
Frye, 566 U.S. at 148. All of this demonstrates that the proof of
prejudice must be matched to the circumstances of the defi-
cient performance and the relief sought.
    Brock-Miller, who began this process pro se, has asserted in
various ways that, but for counsel’s deficient performance, the
outcome of the proceedings would have been different. In
particular, she has argued that the sentencing court would
have dismissed the section 851 information, which would have
afforded Brock-Miller much greater leverage in plea negotia-
tions. With a correct ruling on an appropriate objection to the
section 851 information, she would not have been subject to the
severe doubling effect of the recidivist enhancement. She
would have had much less to lose by going to trial, she
contends, because she would have faced a smaller sentence
and the government would have been required to prove that
the full kilogram of heroin charged in the indictment was
foreseeable to someone who joined the conspiracy at the very
end, in a deal involving only 54 grams of heroin. With a
28                                                    No. 16-3050

guidelines range of 92–115 months (a range that would now be
77 to 96 months, see footnote 4 supra), she would have had
little incentive to agree to a 120-month term of imprisonment,
she maintains.
    She asserts that, if counsel had not been deficient, she either
would have gone to trial or negotiated a more favorable plea
agreement. Hill sets the standard for prejudice for her claim
that she would have gone to trial, and Frye comes closest to
setting the standard for a claim to renegotiate the plea without
the specter of an improper recidivist enhancement looming
over the proceedings. Hill, 474 U.S. at 59 (the defendant must
show that there is a reasonable probability that, but for coun-
sel’s errors, he would not have pleaded guilty and would have
insisted on going to trial); Frye, 566 U.S. at 147 (“To establish
prejudice in this instance, it is necessary to show a reasonable
probability that the end result of the criminal process would
have been more favorable by reason of a plea to a lesser charge
or a sentence of less prison time.”). The government denies that
it would have offered any other deal. That claim is somewhat
belied by the deals the government did offer to other co-
conspirators. Brock-Miller notes that the government made
much more favorable deals with many of the other charged co-
conspirators. Indeed, Oscar Perez, one of the Indiana prisoners
who led the entire conspiracy, received a sentence identical to
that of Brock-Miller. Brock-Miller also points to more than half
a dozen co-conspirators who were allowed to plead guilty to
reduced drug quantities or lesser included offenses. The
district court denied Brock-Miller any hearing on her section
2255 motion based on its erroneous conclusion that counsel’s
performance was not deficient. Brock-Miller has presented
No. 16-3050                                                            29

sufficient evidence to justify a hearing on both deficient
performance and prejudice under Strickland. Martin, 789 F.3d
at 706 (in a section 2255 proceeding, a district court must grant
an evidentiary hearing if the petitioner alleges facts that, if
proven, would entitle him to relief). We therefore reverse the
judgment of the district court, and remand for a hearing on the
questions of whether counsel’s performance was deficient and,
if so, whether Brock-Miller was prejudiced by counsel’s errors.
                                      III.
    When Brock-Miller was convicted under Indiana Code § 16-
42-19-18, the factual basis for the charge was that she used the
syringe to inject heroin. But heroin is not a legend drug and, in
2007, the statute prohibited the use of syringes only in connec-
tion with legend drugs. Brock-Miller mentioned in her pro se
section 2255 motion to the district court that she was seeking
to vacate in state court the very conviction that served as the
predicate for a recidivist sentence. After the district court
denied her section 2255 motion, the state court ruled in Brock-
Miller’s favor on her due process challenge to her Indiana
conviction, concluding that Brock-Miller had not actually
violated the Indiana statute because heroin is not a legend
drug.
   Once counsel was appointed in the instant appeal, Brock-
Miller filed a Rule 60(b) motion to vacate the judgment in the
case now on appeal because it relied on the now-vacated state
court judgment.9 Once the appeal was filed, though, the district


9
    Brock-Miller conceded in her counseled Rule 60(b) motion that she did
                                                            (continued...)
30                                                           No. 16-3050

court was divested of jurisdiction to consider that motion.
Brock-Miller simultaneously filed a Rule 62.1 “Motion for
Indicative Ruling,” asking the court to indicate how it would
rule on the Rule 60(b) motion if it had jurisdiction. Both of
those motions remain pending in the district court.
    Brock-Miller has presented substantial evidence that her
lawyer in her federal criminal case made a series of factual and
legal errors that could amount to deficient performance. She
persuasively asserts that competent counsel would not have
advised a client to accept the proffered plea agreement under
these circumstances, and that she would have insisted on going
to trial rather than accept these terms. We now know that the
Indiana conviction, the entire basis for the recidivist enhance-
ment, has been vacated on the ground that Brock-Miller did
not violate the statute. On remand, the court should expedi-
tiously hold a hearing to resolve the questions of whether
counsel’s performance was deficient, and if so, whether Brock-


9
  (...continued)
not alert the district court in her section 2255 proceedings to her pending
state court post-conviction proceedings. Although she may not have
adequately alerted the district court to the nature of her state court
challenge and the attendant need to hold her section 2255 motion in
abeyance pending the resolution of that challenge, she did mention the
state court proceeding in paragraph 14, page 12, of her section 2255
motion. In response to the question whether she had “any motion,
petition, or appeal now pending (filed and not decided yet) in any court
for the judgment you are now challenging,” she checked the “yes” box
and specified, “Montgomery County Indiana Cause No. 54C01-0709-FC-
00122 Post conviction relief. Fifth and Sixth Amendment violations.”
That was the very conviction cited by the government in its section 851
information.
No. 16-3050                                               31

Miller was prejudiced by that performance. The district court
may also consider Brock-Miller’s pending motions under Rules
60(b) and 62.1.
                            REVERSED AND REMANDED.
