THACKER, Circuit Judge:
On March 24, 2016, a grand jury indicted Sergio Carrillo Murillo ("Appellant") for conspiracy to distribute and possession with intent to distribute cocaine. Three months later, Appellant pled guilty to conspiracy
to distribute cocaine, in violation of
21 U.S.C. §§ 841
(a)(1) and 846.
Following his arrest, and throughout the plea negotiation process, Appellant's purported primary concern was the impact a criminal conviction could have on his status as a lawful permanent resident of the United States. His attorney advised him that, if he pled guilty to the lesser included offense, deportation was a mere possibility that he could fight in immigration court. But Appellant's attorney was wrong: conspiracy to distribute cocaine is an "aggravated felony" under the Immigration and Nationality Act,
see
8 U.S.C. § 1101
(a)(43)(B), and a noncitizen convicted of such a crime is subject to
mandatory
deportation,
see
id.
§ 1227(a)(2)(A)(iii).
On September 7, 2017, Appellant moved under
28 U.S.C. § 2255
to vacate his conviction on the ground that he received ineffective assistance of counsel in violation of the Sixth Amendment. The district court denied his motion, and Appellant appealed. For the reasons that follow, we reverse the decision of the district court and remand for further proceedings.
I.
In 1995, when Appellant was seven years old, he and his family moved from Mexico to the United States. Appellant has lived in the United States ever since. Today, Appellant is a lawful permanent resident. He no longer has family in Mexico, and he is engaged to be married to an American citizen. As such, "[s]taying in the United States with [his] family has always been [his] number one priority." J.A. 65.
1
Twenty-one years after he came to the United States, Appellant got into some legal trouble. On February 10, 2016, Appellant traveled with another man from New Mexico to Virginia to sell a kilogram of cocaine. Unknowingly, the pair sold the drugs to a confidential informant. The confidential informant recorded the transaction while law enforcement officers observed it. After the exchange, Appellant was arrested. On March 24, 2016, a grand jury indicted Appellant on two counts of cocaine-related offenses: (1) conspiracy to distribute in violation of
21 U.S.C. §§ 841
(a) and 846 ; and (2) possession with intent to distribute in violation of
21 U.S.C. § 841
(a)(1) and
18 U.S.C. § 2
.
Shortly after his arrest, Appellant retained attorney Katherine Martell ("Martell") to represent him. Given his circumstances, Appellant wanted an attorney with immigration law experience, and he had heard Martell touting her knowledge of immigration law on Spanish radio.
2
On Appellant's behalf, Martell negotiated a plea agreement with the Government. The Government offered to drop the possession with intent to distribute charge if Appellant would plead guilty to the conspiracy charge. That deal allowed Appellant to avoid a mandatory minimum sentence
of five years.
See
21 U.S.C. § 841
(b)(1)(B)(ii). After discussing a draft of the plea agreement with Appellant, Martell noted in the margin of the draft, "Ask to omit immigration waivers." J.A. 109. Specifically, Martell sought to omit five immigration-related clauses from the draft:
• (1) "Consent Given for Removal from the United States" (which would have required Appellant not to contest removal proceedings brought against him);
• (2) "Waiver of Rights Related to Removal from the United States" (which would have required Appellant to waive his rights to apply for all forms of relief or protection from removal or deportation);
• (3) "Exception for Changed Circumstances Arising After Plea" (which would have allowed Appellant to apply for asylum, withholding of removal, or protection under Article 3 of the Convention Against Torture based
only
on circumstances arising after the entry of his plea);
• (4) "Abandonment of Pending Applications for Relief from Removal" (which would have required Appellant to abandon any existing immigration benefit he holds or any pending application for relief from removal or deportation); and
• (5) "The Defendant's Cooperation in the Defendant's Removal" (which would have required Appellant to agree to assist the Department of Homeland Security in any future removal proceedings).
Id.
at 108-10
.
Indeed, Martell successfully negotiated with the Government to omit from the final plea agreement those five clauses and one more: "Plea Agreement Binding for Purposes of Removal Proceedings" (requiring Appellant to acknowledge that his waiver of immigration-related rights is binding in any future removal proceedings).
Compare
id.
at 108-110
(draft plea agreement),
with
Supp. J.A. Vol. I at 1-13 (final plea agreement).
However, although it did not include an explicit waiver of rights related to removal from the United States, the final plea agreement did mention potential immigration consequences. Specifically, the plea agreement acknowledged that deportation was a
possibility
and provided that Appellant wanted to plead guilty regardless:
[Appellant] recognizes that pleading guilty may have consequences with respect to [Appellant's] immigration status if [Appellant] is not a citizen of the United States. Under federal law, a broad range of crimes are removable offenses, including the offenses to which [Appellant] is pleading guilty. Because removal and other immigration consequences are the subjects of a separate proceeding, [Appellant] understands that no one, including [Appellant's] attorney or the District Court, can predict to a certainty the effect of [Appellant's] conviction on [Appellant's] immigration status. [Appellant] nevertheless affirms that [Appellant] wants to plead guilty regardless of any immigration consequences that [Appellant's] plea may entail, even if the consequence is [Appellant's] automatic removal from the United States.
Supp. J.A. Vol. I at 10-11. Crucially, throughout her discussions with Appellant regarding the plea agreement, Martell assured Appellant that he would be able to fight deportation in immigration court.
On June 21, 2016, Appellant pled guilty to the conspiracy charge. At Appellant's plea hearing, both Martell and the district court characterized the likelihood of deportation flowing from Appellant's plea as a
possibility
: First, after Martell informed
the district court that Appellant was a lawful permanent resident, the district court asked, "Possibility of deportation then?" Martell responded, "Possibility." J.A. 16. Second, the district court informed Appellant that he "
may be
deported" as a result of his plea.
Id.
at 21
(emphasis supplied). Appellant then confirmed that he understood that he "
may
be deported" as a result of his plea.
Id.
(emphasis supplied). He also acknowledged that he reviewed and understood his plea agreement.
After finding that Murillo was competent to enter his plea and that his plea was knowing, voluntary, and supported by facts, the district court accepted it. Appellant then pled guilty to an "aggravated felony" under the Immigration and Nationality Act.
See
8 U.S.C. § 1101
(a)(43)(B) (defining "aggravated felony" as "illicit trafficking in a controlled substance (as defined in section 802 of Title 21), including a drug trafficking crime (as defined in section 924(c) of Title 18)"). Any noncitizen -- including a lawful permanent resident -- who pleads guilty to an "aggravated felony" is subject to mandatory deportation.
See
id.
§ 1227(a)(2)(A)(iii) ("Any alien who is convicted of an aggravated felony at any time after admission is deportable.");
see also
Lee v. United States
, --- U.S. ----,
137 S. Ct. 1958
, 1963,
198 L.Ed.2d 476
(2017) (noting that a lawful permanent resident who pled guilty to an "aggravated felony" was "subject to mandatory deportation").
Thereafter, on September 8, 2016, the district court sentenced Appellant to 24 months in prison and three years of supervised release. Approximately six months later, while Appellant was incarcerated, he learned from an immigration officer that, upon completion of his sentence, he would be deported.
On September 7, 2017, Appellant filed a motion under
28 U.S.C. § 2255
to vacate his conviction, asserting that his attorney had provided him constitutionally ineffective assistance of counsel. Appellant filed several affidavits in support of his motion. In his affidavit, Appellant stated that at no time did Martell inform him that he would be deported if he pled guilty. To the contrary, in her affidavit, Appellant's fiancée stated that when she asked Martell if Appellant's sentence of 24 months would affect his residency, Martell responded, "[N]o because [Appellant] had been a resident for over twenty years that would help him stay here." J.A. 68. Similarly, Appellant's fiancée's mother stated in her affidavit that Martell asserted, "because [Appellant] had already been here for over twenty years, he would not be deported."
Id.
at 70
. Likewise, Appellant's mother stated in her affidavit that, when asked whether Appellant's sentence would affect his residency in the United States, Martell assured her that "it would not."
Id.
at 72
.
Notably, in his affidavit, Appellant explained the significance of Martell's advice:
If I had known that by pleading guilty I would be deported from this country, I would have asked for a jury trial and tried to win my case even if the chances of winning might be small and I might get more prison time. At least I would have a chance, even if small. I would have also asked Ms. Martell to try to get a different plea bargain that would not get me deported. At least she could try! I had never been in trouble like this before.
J.A. 65.
On April 16, 2018, the district court ordered Martell to file a declaration responding to Appellant's claims. In her declaration, Martell acknowledged that Appellant "wanted to try and fight his immigration case" and that she advised him "that he would have to [do so] in immigration court," and claimed that she advised Appellant
to hire an immigration attorney. J.A. 98.
3
Martell also acknowledged that Appellant "expressed his desire to fight his immigration case" but stated that "[Appellant's] focus was reducing prison time" and "there was no plea offer available to [Appellant] that could have avoided immigration consequences." J.A. 98.
On June 26, 2018, without holding an evidentiary hearing, the district court denied Appellant's motion to vacate his conviction. Without addressing Martell's performance, the district court concluded that Appellant failed to present "any evidence that it would have been rational under the circumstances to reject the plea offer that did not subject to him a mandatory five-year sentence." J.A. 183. In reaching that conclusion, the district court highlighted that Appellant "could not avoid the mandatory immigration consequences were he convicted of any of the charges brought against him" and that Appellant's plea agreement indicated that Appellant "want[ed] to plead guilty regardless of any immigration consequences."
Id.
On July 3, 2018, Appellant filed a Rule 59(e) motion for reconsideration. A week later, the district court denied that motion too. In doing so, the district court doubled down on its reasoning:
Dispositive for the Court ... is that [Appellant's] contention - - that he would not have ple[d] guilty had he known the immigration consequences -- is fundamentally inconsistent with his acknowledgement in his Plea Agreement that "[Appellant] wants to plead guilty regardless of any immigration consequences that [Appellant]'s plea may entail, even if the consequences is the [Appellant]'s automatic removal from the United States." Because of this acknowledgement, the Court concluded that [Appellant] had failed to establish the prejudice prong of the
Strickland
[
v. Washington
,
466 U.S. 668
,
104 S.Ct. 2052
,
80 L.Ed.2d 674
(1984) ] analysis. To have concluded otherwise would undermine plea negotiations and the finality of convictions because of future events that were foreseen and addressed at the time in a formal plea agreement based on whether a defendant really meant what he had agreed to in order to obtain a negotiated plea.
J.A. 198-99 (citations omitted).
Nevertheless, the district court granted Appellant a certificate of appealability "with respect to the application of
Lee
[,
137 S. Ct. at 1958
(finding a defendant can demonstrate that his plea was caused by ineffective assistance of counsel by showing a reasonable probability that, by for his counsel's errors, he would have gone to trial rather than accepting the plea) ] to the facts of this case," including whether certain language in Appellant's plea agreement had "the dispositive effect" the district court attributed to it. Order,
United States v. Murillo
, No.
16-cr-00073 (E.D. Va. Mar. 24, 2016; filed July 11, 2018), ECF No. 102. Appellant noted a timely appeal.
II.
We review a district court's denial of a
28 U.S.C. § 2255
motion de novo.
See
United States v. Luck
,
611 F.3d 183
, 186 (4th Cir. 2010). In doing so, we resolve any factual ambiguities in the light most favorable to the movant.
See
United States v. Poindexter
,
492 F.3d 263
, 267 (4th Cir. 2007).
III.
The Sixth Amendment guarantees criminal defendants effective assistance of counsel.
See
Strickland v. Washington
,
466 U.S. 668
, 685-86,
104 S.Ct. 2052
,
80 L.Ed.2d 674
(1984). And that guarantee extends to the plea-bargaining process.
See
Missouri v. Frye
,
566 U.S. 134
, 140-44,
132 S.Ct. 1399
,
182 L.Ed.2d 379
(2012) ;
see also
Lafler v. Cooper
,
566 U.S. 156
, 162,
132 S.Ct. 1376
,
182 L.Ed.2d 398
(2012). To demonstrate that he was denied the effective assistance of counsel, Appellant must show that his counsel's performance was deficient and that he was prejudiced as a result.
Strickland
,
466 U.S. at 687
,
104 S.Ct. 2052
.
The district court held Appellant could not demonstrate that he was denied effective assistance of counsel. Without addressing whether Appellant's attorney's performance was deficient, the district court concluded Appellant could not satisfy
Strickland
's prejudice prong because his plea agreement provided that he "want[ed] to plead guilty
regardless
of any immigration consequences" even if those consequences included "automatic removal from the United States." J.A. 198-99 (emphasis supplied). We hold, however, that a single line from a plea agreement cannot bear the weight the Government would like. When the balance of the evidence is considered here, it is clear Appellant demonstrated a reasonable probability that, had he fully understood the immigration implications of his guilty plea, he would not have pled guilty. Because the district court did not consider whether Appellant's attorney's performance was deficient, we decline to address the issue. Instead, the district court should consider it on remand. In this regard, we are confident our current precedent sheds sufficient light on the appropriate standard.
See
United States v. Swaby
,
855 F.3d 233
, 240 (4th Cir. 2017) ("Effective representation by counsel requires that counsel provide correct advice when the deportation consequences are clear.").
A.
To demonstrate prejudice, a criminal defendant must prove that there is a reasonable probability that, without his counsel's deficient performance, the result of the proceeding in which the deficiency occurred would have been different.
See
Strickland
,
466 U.S. at 694
,
104 S.Ct. 2052
. That requirement applies even when the constitutionally deficient performance affects the outcome of the plea process.
See
Hill v. Lockhart
,
474 U.S. 52
, 58-59,
106 S.Ct. 366
,
88 L.Ed.2d 203
(1985).
But in the context of a plea bargain, the defendant is the master of the outcome. And unlike a judge or a jury, the defendant has an incentive to claim, in retrospect, that the result of the plea process would have been different regardless of whether that claim is, in fact, true.
Cf.
Lee v. United States
, --- U.S. ----,
137 S. Ct. 1958
, 1967,
198 L.Ed.2d 476
(2017) ("Courts should not upset a plea solely because of post hoc assertions from a defendant about how he would have [pled] but for his attorneys' deficiencies."). Thus,
to prevent criminal defendants with bargainer's remorse from simply claiming they would not have taken a deal but for a bit of bad advice, we require defendants asserting deficiencies in the plea-bargaining process to provide evidence of their sincerity.
See
id.
("Judges should ... look to contemporaneous evidence to substantiate a defendants' expressed preferences."). That is to say, when deficient performance causes a defendant to accept a plea bargain he might not have otherwise, the defendant must point to evidence that demonstrates a reasonable probability that, with an accurate understanding of the implications of pleading guilty, he would have rejected the deal.
B.
Here, we conclude that the district court erred by giving dispositive weight to limited language from Appellant's plea agreement. The district court twice concluded (and the Government maintains) that Appellant could not (and according to the Government cannot) demonstrate prejudice because a single line in his plea agreement -- that is, "[Appellant] wants to plead guilty regardless of any immigration consequences that defendant's plea may entail, even if the consequence is the defendant's automatic removal from the United States" -- undermines his assertion that he would not have pled guilty had he known he would be deported. J.A. 108. Instead of weighing evidence that Appellant would have rejected the plea agreement had he known it carried a consequence of mandatory deportation against the evidence that Appellant would have accepted it nonetheless, the district court found that single line "dispositive."
Id.
at 198. We disagree.
Giving dispositive weight to boilerplate language from a plea agreement is at odds with
Strickland
's fact-dependent prejudice analysis. To determine whether a defendant was prejudiced by an attorney error,
Strickland
requires courts to undertake an individualized examination of the proceedings in which the error is alleged.
See
Strickland
,
466 U.S. at 691-96
,
104 S.Ct. 2052
;
cf.
id.
at 693
,
104 S.Ct. 2052
("[Attorney errors] cannot be classified according to likelihood of causing prejudice."). The prejudice analysis in the context of the plea-bargaining process requires a fact-based evaluation of the weight of the evidence.
See, e.g.
,
Premo v. Moore
,
562 U.S. 115
, 129-130,
131 S.Ct. 733
,
178 L.Ed.2d 649
(2011) (rejecting a "per se rule of prejudice"). Accordingly, a categorical rule affording dispositive weight to a prior statement is "ill suited to an inquiry that ... demands a 'case-by-case analysis.' "
Lee
,
137 S. Ct. at 1966
(quoting
Williams v. Taylor
,
529 U.S. 362
, 391,
120 S.Ct. 1495
,
146 L.Ed.2d 389
(2000) ). In
Lee
, the Supreme Court rejected the Government's invitation to find that a defendant with no viable defense can
never
show prejudice resulting from the denial of his right to trial.
See
id.
There is no reason to believe the Supreme Court would be more willing to find that a defendant who affirmed, by means of boilerplate plea agreement language, that he would have pled guilty regardless of any immigration consequences can
never
demonstrate that he would have rejected the deal but for his counsel's ineffective assistance.
Indeed, the weight the district court accorded Appellant's plea agreement cannot be squared with this court's decision in
Swaby
. Swaby's plea agreement included nearly identical language to that at play here: "[C]onviction for a broad range of crimes can lead to adverse immigration consequences, including automatic removal from the United States .... Defendant understands that no one, including his attorney or the Court, can predict with certainty the effect of a conviction
on immigration status. Defendant nevertheless affirms that he wants to plead guilty regardless of any potential immigration consequences."
See
Swaby
,
855 F.3d at 237
(alterations in original). Nonetheless, this court found that Swaby demonstrated prejudice. Rather than simply consider the boilerplate language included in Swaby's plea agreement dispositive, we weighed that language against Swaby's connections to this country.
See
id.
at 243
. After doing so, we concluded it was not only "reasonably likely" but also "unsurprising" that Swaby, had he known the true consequences of his guilty plea, "would have taken any chance,
no matter how slim
, to avoid deportation."
Id.
at 244
(emphasis in original).
4
To be sure, language from plea agreements and statements made during plea hearings are not irrelevant.
See
United States v. Lemaster
,
403 F.3d 216
, 221-22 (4th Cir. 2005) ("[I]n the absence of extraordinary circumstances, the truth of sworn statements made during a Rule 11 colloquy is conclusively established, and a district court should, without holding an evidentiary hearing, dismiss any § 2255 motion that necessarily relies on allegations that contradict the sworn statements."). But plea agreement language and sworn statements must be considered in their context: When a defendant has been told -- multiple times -- that immigration consequences are not mandated but merely a "possibility," a willingness "to plead guilty regardless of any immigration consequences" does not mean that the defendant was willing to plead guilty if doing so meant
mandatory
deportation.
Cf.
United States v. Rodriguez-Vega
,
797 F.3d 781
, 790 n.9 (9th Cir. 2015) ("[T]he effectiveness of th[e] written warning was substantially diminished by the context in which it was given,
i.e.
the oral statements by [the defendant's] counsel and the court that [the defendant] faced only a possibility of removal."). The mere utterance and existence of such statements and language -- without context -- cannot conclusively determine that a defendant would have pled guilty regardless of the immigration consequences of doing so.
C.
The question that remains, then, is whether, considering the weight of the evidence, Appellant satisfied his burden to demonstrate a reasonable probability that, without his counsel's deficient performance, he would not have pled guilty. To do so, Appellant need not demonstrate that rejecting the plea agreement was "the best objective strategy or even an attractive option."
Swaby
,
855 F.3d at 244
. He need only demonstrate that, from the perspective of a reasonable person in his position, rejecting the plea agreement would have been "rational."
Id.
Often, "deportation is an integral -- indeed, sometimes the
most important part -- of the penalty that may be imposed on noncitizen defendants who plead guilty."
Padilla v. Kentucky
,
559 U.S. 356
, 364,
130 S.Ct. 1473
,
176 L.Ed.2d 284
(2010). To be sure, "preserving [a] client's right to remain in the United States may be more important to the client than any potential jail sentence."
Id.
at 368
,
130 S.Ct. 1473
. Accordingly, to determine whether a particular defendant would have rejected a plea deal, we look to evidence regarding what is important to the defendant asserting the ineffective assistance claim.
See, e.g.
,
Swaby
,
855 F.3d at 244
.
The record here leaves little doubt that avoiding deportation was Appellant's main priority. Appellant retained Martell because he believed she had immigration experience: Indeed, Martell held herself out as being uniquely experienced in matters of immigration. Appellant told Martell that he was determined to fight deportation: Martell acknowledged that she and Appellant discussed immigration extensively, that Appellant "expressed his desire to fight his immigration case," and that she informed Appellant that he had to "fight his case" in immigration court. J.A. 98. Appellant also endeavored to retain his immigration-related rights: Drafts of the plea agreement demonstrate that Appellant and Martell were focused on immigration consequences during the negotiation process. Toward that end, Martell wrote herself a note to "[a]sk to omit immigration waivers" and negotiated to omit sections such as "Consent Given for Removal from the United States" and "Waiver of Rights Related to Removal from the United States."
Id.
at 108-109. Had Appellant truly intended to plead guilty to an offense even if it triggered mandatory deportation, he would have had little reason to pursue these negotiations.
Moreover, Appellant's mother, fiancée, and fiancée's mother asked Martell about the immigration consequences of his conviction and sentence. When Appellant's fiancée asked Martell if Appellant's sentence of 24 months would affect his residency, Martell responded, "[N]o because [Appellant] had been a resident for over twenty years that would help him stay here." J.A. 68. Consistent with this statement, Appellant's fiancée's mother averred that Martell said, "because [Appellant] had already been here for over twenty years, he would not be deported."
Id.
at 70.
Most significantly, Appellant has lived in the United States since he was seven years old. His family and his life are here in the United States. And according to Appellant, "[i]f [he] had known that by pleading guilty [he] would be deported from this country, [he] would have asked for a jury trial and tried to win [his] case even if the chances of winning might be small and [he] might get more prison time." J.A. 65.
Appellant's affirmations that he understood that he might be deported do not outweigh the evidence that avoiding deportation was more important to Appellant than any jail sentence. The district court understood the sentence "defendant wants to plead guilty regardless of any immigration consequences that defendant's plea may entail, even if the consequence is the defendant's automatic removal from the United States," to directly contradict Appellant's position that, had he known his plea carried a mandatory-deportation consequence, he would not have taken it. J.A. 199. But the sentence is not that definitive. The sentence includes the equivocal phrases "may entail" and "even if." Moreover, the line before this sentence underscores the qualifying language: "[t]he defendant recognizes that pleading guilty
may
have consequences with respect to defendant's
immigration status if defendant is not a citizen of the United States." Supp. J.A. Vol. I at 10 (emphasis added). These statements simply do not suggest that
mandatory
deportation would
not
have changed Appellant's mind. This is even more clear when considered in conjunction with the advice Appellant was receiving. Of course Appellant was willing to sign a plea agreement that said he "wants to plead guilty regardless of any immigration consequences" when he had been told -- multiple times -- that immigration consequences were merely a "possibility."
Nor, for that matter, did the district court's general warning cure any ineffective assistance. Although a district court can, by accurately informing a defendant of the immigration consequences of his plea, cure an attorney's incorrect advice,
see, e.g.
,
United States v. Hernandez-Monreal
,
404 F. App'x 714
, 715 (4th Cir. 2010), "general and equivocal" warnings do not suffice,
United States v. Akinsade
,
686 F.3d 248
, 250 (4th Cir. 2012). In
Akinsade
, the district court warned the defendant that, because his guilty plea, he "may be deported."
Id.
at 250
. We found that warning to be "insufficient to correct counsel's affirmative misadvice" that the defendant's crime "was not categorically a deportable offense."
Id.
at 254
. We noted that, although the warning "touch[ed] upon the consequence of deportation," it did not "correct the particular misadvice given by counsel."
Id.
at 255
. Here, as in
Akinsade
, the district court's warning that Appellant "may be deported" was insufficient to cure Martell's misadvice that his crime was not a categorically deportable offense. The district court's warning, like the warning at issue in
Akinsade
, was "general and equivocal."
Id.
at 250 ;
see also
Dat
, 920 F.3d at 1195-96 (finding a presentence report that noted the defendant would be subject to "Administrative Removal" was insufficient to remedy his attorney's misadvice that he would not be deported). Moreover, it came moments after Martell stated on the record that Appellant faced merely a "[p]ossibility" of deportation. J.A. 16.
The balance of evidence here weighs in favor of Appellant. Appellant prioritized immigration in the plea negotiation process and had a significant reason to do so: avoiding mandatory separation from his family and his home. The qualified statements from Appellant's plea agreement and equivocal affirmations at his plea hearing do not outweigh the evidence that Appellant's main priority was remaining in this country with his family. Accordingly, we find the evidence demonstrates a reasonable probability that, had Appellant known the true and certain extent of the consequences of his guilty plea, he would have refused it.
IV.
We reverse the district court's judgment and remand to the district court for further proceedings consistent with this opinion.
REVERSED AND REMANDED