MEMORANDUM & ORDER
JOHN W. LUNGSTRUM UNITED STATES DISTRICT JUDGE
In December 2007, defendant Jeremy Gilmore, along with multiple co-conspirators, was charged with conspiracy to distribute and to possess with intent to distribute more than 50 grams of methamphetamine. In May 2009, Mr. Gilmore was convicted by a jury and, thereafter, the court imposed the mandatory minimum sentence of life imprisonment in light of Mr. Gilmore’s two prior convictions for felony drug offenses. See 21 U.S.C. § 841(b)(1)(A)(vii). The Tenth Circuit affirmed Mr. Gilmore’s conviction and Mr. Gilmore then filed a motion to vacate his sentence pursuant to 28 U.S.C. § 2255. In his petition, Mr. Gilmore asserted that the performance of his counsel was deficient in a number of respects, including that his counsel failed to advise him sufficiently concerning whether to plead guilty instead of proceeding to trial. The court granted Mr. Gilmore’s request for an evidentiary hearing on that claim, which it retained under advisement, appointed counsel for litigation of that claim, and dismissed the petition in all other respects.
On January 28, 2013, the court held an evidentiary hearing on the claim. Mr. Gilmore was represented by Brandon Bell and the government was represented by Assistant United States Attorney Scott Rask. The evidence presented at the hearing focused on several key issues pertinent to Mr. Gilmore’s claim, including whether his counsel failed to meaningfully communicate to him the government’s plea offers; whether his counsel failed to advise him that a conviction at trial would guarantee him a life sentence in light of his two prior felony drug convictions; whether his trial counsel should have negotiated and secured a plea agreement prior to the government’s filing of an information under 21 U.S.C. § 851; and whether his trial counsel lacked sufficient knowledge of the federal drug conspiracy laws such that she misinformed Mr. Gilmore about his likelihood of success at trial. As explained in more detail below, the court concludes that Mr. Gilmore received constitutionally deficient representation in each of these respects and that such representation undoubtedly prejudiced the outcome of the case. Thus, the court finds that Mr. Gilmore is entitled to relief on that portion of his § 2255 petition that it had previously retained under advisement. As to the actual remedy, the court directs Mr. Bell and Mr. Rask to meet and confer concerning an appropriate remedy for the constitutional violation that occurred. If the parties are unable to agree on an appropriate remedy (subject to the court’s approval), then, consistent with the parties’ requests, the court will permit the parties to submit supplemental briefing on the issue of an appropriate remedy and will schedule a hearing on the issue.
Title 28 U.S.C. § 2255 entitles a prisoner to relief “[i]f the court finds that the judgment was rendered without jurisdiction, or that the sentence imposed was not authorized by law or otherwise open to collateral attack, or that there has been such a denial or infringement of the constitutional rights of the prisoner as to render the judgment vulnerable to collateral attack.” Id. The remedy under § 2255, then, does not encompass all claimed errors in conviction and sentencing; rather, the claimed error must constitute a “fundamental defect which inherently results in a complete miscarriage of justice.” United States v. Blackwell, 127 F.3d 947, 954 (10th Cir. 1997) (quotations and citations omitted).
To obtain relief in the particular context of an ineffective assistance of counsel claim, Mr. Gilmore must establish both that his counsel’s performance was deficient and that he was thereby prejudiced. Strickland v. Washington, 466 U.S. 668, 687 (1984). With respect to the performance prong, Mr. Gilmore must overcome a “strong presumption that counsel’s representation was within a wide range of reasonable professional assistance.” Harrington v. Richter, 131 S.Ct. 770, 787 (2011) (internal quotations omitted). To overcome that presumption, he must show that counsel “failed to act reasonably considering all the circumstances.” Cullen v. Pinholster, 131 S.Ct. 1388, 1403 (2011) (internal quotations omitted). In other words, Mr. Gilmore must show that his counsel made “errors so serious that counsel was not functioning as the ‘counsel’ guaranteed the defendant by the Sixth Amendment.” United States v. Rushin, 642 F.3d 1299, 1307 (10th Cir. 2011) (quoting Harrington, 131 S.Ct. at 787).
With respect to the prejudice prong, Mr. Gilmore must “demonstrate a ‘reasonable probability’ that, but for counsel’s unprofessional errors, the result of the proceeding would have been different.” Rushin, 642 F.3d at 1309 (quoting Harrington, 131 S.Ct. at 787). A “reasonable probability” is one “sufficient to undermine confidence in the outcome.” Id. at 1310 (quoting Strickland, 466 U.S. at 694). Confidence in the outcome is undermined only when “the likelihood of a different result is substantial, not just conceivable.” Id.
The following facts are either reflected from the docket in this case or from the testimony of witnesses at the evidentiary hearing.
As noted earlier, Mr. Gilmore was indicted in December 2007. In early January 2008, the court appointed an attorney to represent Mr. Gilmore. This attorney (hereinafter referred to as “initial counsel”) testified at the evidentiary hearing concerning his representation of Mr. Gilmore—representation that, in light of a potential conflict of interest that surfaced, lasted only five or six weeks. During initial counsel’s representation of Mr. Gilmore, they met on three separate occasions to discuss various aspects of Mr. Gilmore’s case. As reflected in handwritten notes of initial counsel (Exh. 401), he and Mr. Gilmore, on January 14, 2008, discussed Mr. Gilmore’s criminal history. Although initial counsel testified that he was made aware of only one prior felony drug conviction in Mr. Gilmore’s history, counsel’s meeting notes reflect a discussion of “possession of meth” in “Barry Co.” and “trafficking” in “Lawrence Co., ” referring, as confirmed by initial counsel, to the respective counties in which Mr. Gilmore had prior cases. Mr. Gilmore testified that he advised initial counsel about convictions in both Barry County and Lawrence County.
According to initial counsel, he received a proposed, unsolicited plea agreement via email from the prosecuting attorney on January 30, 2008. The proposed plea agreement required Mr. Gilmore’s cooperation in exchange for the government’s agreement to request a 3-level reduction for acceptance of responsibility and to request a reduced sentence below any statutory minimum upon a determination that Mr. Gilmore provided substantial assistance to the government. Exh. 404. Although he provided a copy of this proposed plea agreement to Mr. Gilmore (which Mr. Gilmore confirmed at the hearing), initial counsel did not discuss the proposed agreement in any detail with Mr. Gilmore based on initial counsel’s belief that detailed discussions about pleading guilty too early in the process is not helpful to the building of the relationship with a client. Initial counsel testified that he and Mr. Gilmore simply never reached the point of discussing whether to proceed to trial or to negotiate a plea agreement and, in the case of entering a plea agreement, whether to pursue cooperation with the government.
The day after receiving the proposed plea agreement from the prosecutor, initial counsel prepared a sentencing memorandum for Mr. Gilmore consistent with counsel’s standard practice. Exh. 402. During his testimony, Mr. Gilmore confirmed receipt of the memorandum. In that memorandum, initial counsel advised Mr. Gilmore, based on his asserted belief that Mr. Gilmore was a one-time prior drug felon, that Mr. Gilmore faced a possible statutory minimum punishment of 20 years’ imprisonment with a maximum sentence of life imprisonment if he was convicted at trial or pled guilty to the conspiracy charge without an agreement to cooperate with the government. The sentencing memorandum also recognized the possibility that Mr. Gilmore could receive a sentence below the statutory minimum of 20 years if he pled guilty to the conspiracy charge and cooperated with the government. It is undisputed that this memorandum did not mention any circumstance under which Mr. Gilmore might face a mandatory minimum life sentence. Moreover, initial counsel testified that he had no recollection of discussing with Mr. Gilmore at any time what the impact on the statutory minimum would be if he had more than one prior felony drug conviction.
On February 19, 2008, the court granted initial counsel’s motion to withdraw and, two days later, the court appointed substitute counsel for Mr. Gilmore. Initial counsel testified that he forwarded all discovery to Mr. Gilmore’s new counsel, but he had no recollection of forwarding the proposed plea agreement to new counsel. In any event, new counsel (hereinafter referred to as “trial counsel”) testified that Mr. Gilmore’s case was the first federal drug conspiracy case that she ever handled through trial and, at the hearing, she equivocated on whether she was “unfamiliar with federal drug conspiracy law.” She conceded, however, that she was inexperienced in the process and the affidavit she submitted in support of the government’s response to Mr. Gilmore’s § 2255 petition indicates that in March 2008 she “brainstormed” with a more experienced criminal defense attorney “re: defending drug conspiracy cases in general.” Exh. 413.
Trial counsel testified as to the steps she took to familiarize herself with the case upon her appointment beginning in late February 2008. According to trial counsel, she met with Mr. Gilmore on several occasions, researched applicable laws and reviewed the government’s proffer books on at least three occasions. During one or more of her visits to the United States Attorneys’ Office to review proffer books, trial counsel engaged in informal discussions with the prosecutor on the case regarding a potential plea agreement. According to trial counsel, the prosecutor told her that her client was “going to get convicted [so] you need to talk to me about working something out.” Trial counsel testified that the prosecutor, to the best of her recollection, offered “something like 15 or 20 years . . . I want to say 20.” The prosecutor testified that she and trial counsel had several discussions ...