[246]*246HAYNES, Circuit Judge:
After Raymond Christopher Reggie pleaded guilty to five counts of wire fraud, the district court sentenced him to 135 months of imprisonment, two years of supervised release, and ordered him to pay restitution. Reggie now appeals, contending, inter alia, that the district court erred in failing to determine whether his plea was voluntary as required by Federal Rule of Criminal Procedure 11(b)(2) in a way that violated his substantial rights. We agree, and accordingly VACATE the judgment and REMAND for further proceedings,
I. Background
On August 14, 2013, the Government filed an indictment charging Reggie with five counts of wire fraud in violation of 18 U.S.C. § 1343 for allegedly submitting false advertising expenses to his automobile dealership clients.1 The Government and Reggie then engaged in extensive pretrial motions practice,2 and Reggie’s trial was ultimately set for October 20, 2014.
On October 14, Reggie filed a motion to continue his trial, stating that he had suffered a stroke on October 6, 2014, spent three days in an intensive care unit, and remained hospitalized. The motion indicated that Reggie was unable to assist or prepare for trial with his attorneys, nor could he effectively testify at trial as planned. Attached was a note from Reggie’s physician, stating that Reggie suffered from the symptoms of a stroke, was undergoing physical, occupational, and speech therapy, and that he was “not able to prepare for or attend any legal proceedings.” The court granted a seven day continuance and rescheduled the trial for October 27. Reggie’s counsel objected to the trial date, arguing that Reggie’s ability to testify was not known and that counsel would not be ready within a week. The district court declined to change the trial dated unless Reggie’s physician could attest in writing that he was suffering from speech issues, cognitive issues, or was physically unable to be present for trial.
Reggie filed a subsequent motion on October 22, seeking a continuance of at least thirty days. Reggie’s motion informed the court that he was to undergo outpatient surgery on October 22 to place a heart monitor in his chest, and begin outpatient therapy on October 24. It further stated that Reggie’s neurological status could only be evaluated in detail after a neurological consultation scheduled for October 29 — two days after the trial was set to begin — and that the letter attesting to Reggie’s inability to participate at trial could be provided after this appointment. October 29 was the earliest Reggie could obtain this neurological assessment because his surgery on October 22 made an assessment that week unviable. The mo[247]*247tion also noted that Reggie’s speech was not yet normal, he was unable to drive, had difficulty reviewing evidence in preparation for the trial, and that he required -assistance with preparing meals, bathing, getting dressed, and using the restroom. Attached were exhibits including a medical report showing Reggie’s stroke diagnosis, a list of prescribed medications related to his stroke, and appointment confirmations for his scheduled heart surgery and neurological assessment.
The court denied Reggie’s motion for a thirty-day continuance in an order entered on October 23. The court observed that the exhibits proffered by Reggie failed to show that Reggie’s participation at trial would be life threatening, and failed to address Reggie’s speech, cognitive or physical limitations as specifically ordered by the court. The court concluded that defense counsel had five months to prepare for trial and stated perhaps Reggie could attend his neurological assessment on Halloween, when the court intended to take a half day off.
On October 25, Reggie’s counsel informed prosecutors by e-mail that Reggie would plead guilty to the wire fraud charges two days later, the day the trial was scheduled to begin. After being notified of this proposed plea, the courtroom deputy advised Reggie’s counsel that, “[the district judge] wanted counsel to be advised that should Mr. Reggie not enter a guilty plea for whatever reason Monday morning, the jury panel has been placed on stand-by and the trial will commence.” On the morning of October 27, Reggie went before the district court and confirmed that he would plead guilty to all five counts of wire iraud without a plea agreement in place. The court acknowledged that Reggie was having difficulty speaking and that his speech was slow. It then went through a plea colloquy with Reggie. However, the court failed to specifically ask Reggie about the voluntariness of his plea. It also did not inform Reggie about his right to counsel, his privilege against self-incrimination, his right to testify and present evidence at trial, and his right to compel the attendance of witnesses. At the conclusion of the plea hearing, Reggie pleaded guilty to all five counts of wire fraud.
After Reggie replaced his previous defense counsel, he filed a motion to withdraw his guilty plea with the court on June 2, 2015. Reggie argued that he was pressured to plead guilty based on his inability to assist 'in his own defense without a continuance after he suffered a stroke. Reggie also maintained that his plea colloquy with the court was defective, as it varied from the requirements of Federal Rule of Criminal Procedure 11. Reggie argued that, in addition to other Rule 11 defects, the court failed to make inquiries about whether his plea was knowing and voluntary. He attached to the motion a medical report from his neurologist related to his October 29 neurological assessment, which stated that Reggie was “[ujnable to speak due to brain lesion.”
On June 17, 2015, the court held a hearing on the motion to withdraw the plea, denied the motion, and proceeded to hold Reggie’s sentencing hearing. In a written ruling, the court explained that based on the questions it had asked Reggie during the plea hearing, Reggie had made a knowing and voluntary decision to plead guilty. It further stated that the Carr3 factors, which govern whether, to grant a motion to withdraw a guilty plea, strongly pointed towards denying Reggie’s motion. With respect to defects in the plea colloquy, the court concluded that the errors were harmless.
[248]*248The district court entered a judgment and sentenced Reggie to the high end of the applicable Guidelines range of 135 months in prison. It also imposed two years of supervised release, and ordered Reggie to pay restitution in the amount of $1,217,657.36. Reggie timely appealed.
II. Discussion
We review challenges to the sufficiency of a plea colloquy de novo. United States v. Lujano-Perez, 274 F.3d 219, 224 (5th Cir. 2001). “Before accepting a plea of guilty ... the court must address the defendant personally in open court and determine that the plea is voluntary and did not result from force, threats, or promises. ...” Fed. R. Crim. P. 11(b)(2).
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[246]*246HAYNES, Circuit Judge:
After Raymond Christopher Reggie pleaded guilty to five counts of wire fraud, the district court sentenced him to 135 months of imprisonment, two years of supervised release, and ordered him to pay restitution. Reggie now appeals, contending, inter alia, that the district court erred in failing to determine whether his plea was voluntary as required by Federal Rule of Criminal Procedure 11(b)(2) in a way that violated his substantial rights. We agree, and accordingly VACATE the judgment and REMAND for further proceedings,
I. Background
On August 14, 2013, the Government filed an indictment charging Reggie with five counts of wire fraud in violation of 18 U.S.C. § 1343 for allegedly submitting false advertising expenses to his automobile dealership clients.1 The Government and Reggie then engaged in extensive pretrial motions practice,2 and Reggie’s trial was ultimately set for October 20, 2014.
On October 14, Reggie filed a motion to continue his trial, stating that he had suffered a stroke on October 6, 2014, spent three days in an intensive care unit, and remained hospitalized. The motion indicated that Reggie was unable to assist or prepare for trial with his attorneys, nor could he effectively testify at trial as planned. Attached was a note from Reggie’s physician, stating that Reggie suffered from the symptoms of a stroke, was undergoing physical, occupational, and speech therapy, and that he was “not able to prepare for or attend any legal proceedings.” The court granted a seven day continuance and rescheduled the trial for October 27. Reggie’s counsel objected to the trial date, arguing that Reggie’s ability to testify was not known and that counsel would not be ready within a week. The district court declined to change the trial dated unless Reggie’s physician could attest in writing that he was suffering from speech issues, cognitive issues, or was physically unable to be present for trial.
Reggie filed a subsequent motion on October 22, seeking a continuance of at least thirty days. Reggie’s motion informed the court that he was to undergo outpatient surgery on October 22 to place a heart monitor in his chest, and begin outpatient therapy on October 24. It further stated that Reggie’s neurological status could only be evaluated in detail after a neurological consultation scheduled for October 29 — two days after the trial was set to begin — and that the letter attesting to Reggie’s inability to participate at trial could be provided after this appointment. October 29 was the earliest Reggie could obtain this neurological assessment because his surgery on October 22 made an assessment that week unviable. The mo[247]*247tion also noted that Reggie’s speech was not yet normal, he was unable to drive, had difficulty reviewing evidence in preparation for the trial, and that he required -assistance with preparing meals, bathing, getting dressed, and using the restroom. Attached were exhibits including a medical report showing Reggie’s stroke diagnosis, a list of prescribed medications related to his stroke, and appointment confirmations for his scheduled heart surgery and neurological assessment.
The court denied Reggie’s motion for a thirty-day continuance in an order entered on October 23. The court observed that the exhibits proffered by Reggie failed to show that Reggie’s participation at trial would be life threatening, and failed to address Reggie’s speech, cognitive or physical limitations as specifically ordered by the court. The court concluded that defense counsel had five months to prepare for trial and stated perhaps Reggie could attend his neurological assessment on Halloween, when the court intended to take a half day off.
On October 25, Reggie’s counsel informed prosecutors by e-mail that Reggie would plead guilty to the wire fraud charges two days later, the day the trial was scheduled to begin. After being notified of this proposed plea, the courtroom deputy advised Reggie’s counsel that, “[the district judge] wanted counsel to be advised that should Mr. Reggie not enter a guilty plea for whatever reason Monday morning, the jury panel has been placed on stand-by and the trial will commence.” On the morning of October 27, Reggie went before the district court and confirmed that he would plead guilty to all five counts of wire iraud without a plea agreement in place. The court acknowledged that Reggie was having difficulty speaking and that his speech was slow. It then went through a plea colloquy with Reggie. However, the court failed to specifically ask Reggie about the voluntariness of his plea. It also did not inform Reggie about his right to counsel, his privilege against self-incrimination, his right to testify and present evidence at trial, and his right to compel the attendance of witnesses. At the conclusion of the plea hearing, Reggie pleaded guilty to all five counts of wire fraud.
After Reggie replaced his previous defense counsel, he filed a motion to withdraw his guilty plea with the court on June 2, 2015. Reggie argued that he was pressured to plead guilty based on his inability to assist 'in his own defense without a continuance after he suffered a stroke. Reggie also maintained that his plea colloquy with the court was defective, as it varied from the requirements of Federal Rule of Criminal Procedure 11. Reggie argued that, in addition to other Rule 11 defects, the court failed to make inquiries about whether his plea was knowing and voluntary. He attached to the motion a medical report from his neurologist related to his October 29 neurological assessment, which stated that Reggie was “[ujnable to speak due to brain lesion.”
On June 17, 2015, the court held a hearing on the motion to withdraw the plea, denied the motion, and proceeded to hold Reggie’s sentencing hearing. In a written ruling, the court explained that based on the questions it had asked Reggie during the plea hearing, Reggie had made a knowing and voluntary decision to plead guilty. It further stated that the Carr3 factors, which govern whether, to grant a motion to withdraw a guilty plea, strongly pointed towards denying Reggie’s motion. With respect to defects in the plea colloquy, the court concluded that the errors were harmless.
[248]*248The district court entered a judgment and sentenced Reggie to the high end of the applicable Guidelines range of 135 months in prison. It also imposed two years of supervised release, and ordered Reggie to pay restitution in the amount of $1,217,657.36. Reggie timely appealed.
II. Discussion
We review challenges to the sufficiency of a plea colloquy de novo. United States v. Lujano-Perez, 274 F.3d 219, 224 (5th Cir. 2001). “Before accepting a plea of guilty ... the court must address the defendant personally in open court and determine that the plea is voluntary and did not result from force, threats, or promises. ...” Fed. R. Crim. P. 11(b)(2). Where, as here, a defendant files a pre-sentencing motion to withdraw his guilty plea, an error under Rule 11 is preserved and subject to review under the harmless error standard. See United States v. Powell, 354 F.3d 362, 367 (5th Cir.2003). “To determine whether a Rule 11 error is harmless (i.e., whether the error affects substantial rights), we focus on whether the defendant’s knowledge and comprehension of the full and correct information would have been likely to affect his willingness to plead guilty.” United States v. Johnson, 1 F.3d 296, 302 (5th Cir.1993). In other words, we examine the facts and circumstances of the case to see if the district court’s flawed compliance with Rule 11 can reasonably be viewed as a material factor affecting a defendant’s decision to plead guilty. Id. In making this determination, we “may consult the whole record.” United States v. Vonn, 535 U.S. 55, 59, 122 S.Ct. 1043, 152 L.Ed.2d 90 (2002). When a situation presents complexity or doubt as to whether a plea was voluntary, we will do a more searching inquiry as to whether Rule 11(b)(2) has been satisfied. See United States v. Henry, 113 F.3d 37, 41 (5th Cir. 1997). The burden rests on the Government to show that a Rule 11 error was harmless. Vonn, 535 U.S. at 62, 122 S.Ct. 1043.
The Government does not dispute that the district court failed to specifically ask Reggie about the voluntariness of his plea, but instead claims that it has met its burden to establish that this violation of Rule 11(b)(2) was harmless. We disagree.
The record clearly shows that Reggie suffered á stroke on October 6, 2014, that required him to spend three days in an intensive care unit, and that his physician confirmed that his medical condition left him unable to prepare for or attend any legal proceedings. Subsequent medical records submitted to the district court further established Reggie’s stroke diagnosis, the therapy he was undergoing as a result of his stroke, as well as his scheduled October 22 heart surgery that would prevent him from undergoing a neurological assessment until October 29. Nevertheless, on October 23, the district court denied his motion for a thirty-day continuance and determined that his trial would commence as scheduled on October 27.
In this fraud case involving advertising expenses (where numbers are important), Reggie’s inability to communicate effectively as a result of his stroke was made apparent during his plea hearing. When asked what the current date was, Reggie responded “October, two seven”; when asked what year it was, he responded “one four”; when asked how old he was, Reggie responded “five three”; and when asked what year he was born, Reggie stated “six one.” When the district court inquired as to whether Reggie was able to attend to his own finances, Reggie, a college-educated man, responded with “I only have my left-hand to push.” When asked if he was able to go through normal daily activities, he answered that “with a little help I can [249]*249bathe. I can — I go to O.T. [occupational therapy] and I couldn’t put the necktie on, I’m sorry,” The court also asked Reggie if he knew what wire fraud meant, to which he responded, “I put the check in the bank and it went out of Louisiana and then made it fraud.”
The obvious communication issues exhibited by Reggie during his plea hearing, buttressed by the medical evidence he provided to the court, helped substantiate his claims that he was unable to assist in his own defense during the relevant period and would be unable to effectively testify on his own behalf.4 Cf. United States v. Graves, 98 F.3d 258, 261-62 (7th Cir.1996) (reversing the conviction of a defendant who suffered a stroke before pleading guilty because the district court failed to sua sponte order a competency hearing with testimony from a neurologist under 18 U.S.C. § 4241, and emphasizing that “Oludges are not experts in assessing the effects of a stroke on mental functioning”); United States v. Crosby, 739 F.2d 1542, 1544-46 (11th Cir.1984) (remanding for a competency hearing when the district court, even after a physician testified that defendant suffered from a neurological disorder and defendant’s counsel expressed an inability to communicate effectively with the defendant, denied the defendant’s motion for a continuance to undergo neurological testing). Reggie’s inability to testify on his own behalf or assist in his own defense was further confirmed by a neurologist’s assessment of Reggie conducted on October 29 (two days after Reggie pleaded guilty), which stated that Reggie was “[u]nable to speak due to brain lesion.” Moreover, Reggie’s communication struggles at the plea hearing stood in marked contrast to his lucidity at the plea withdrawal hearing around seven months later, where Reggie was able to clearly articulate his thoughts.5
While we need not and do not address whether Reggie’s plea was involuntary or whether a competency hearing was required in this case, Reggie’s medical condition undoubtedly created a “complex or doubtful ... situation” that at least raised questions about the voluntariness of his plea, requiring a “more searching ... inquiry” as to whether the requirements of Rule 11(b)(2) were satisfied. Henry, 113 F.3d at 41. This case is thus unlike the many harmless error cases where one omission from the Rule 11 ‘colloquy is clearly inconsequential. See e.g., United States v. Lara-Castro, 561 Fed.Appx. 346, 349 (5th Cir.2014) (affirming under plain error review where defendant was previously advised of his right to counsel).
The pressure imposed on Reggie to plead guilty by his medical condition and [250]*250the denial of the continuance was intensified by the district court’s actions. Faced with the prospect of going to trial despite his inability to communicate effectively, Reggie notified the district court that he was planning to plead guilty. The court responded by stating that “should Mr. Reggie not enter a guilty plea for whatever reason Monday morning, the jury panel has been placed on stand-by and the trial will commence.” (emphasis added). We have stressed the important prohibition against any form of judicial participation in or interference with a defendant’s decision to plead guilty. See United States v. Rodriguez, 197 F.3d 156, 157-59 (5th Cir.1999) (vacating a conviction and sentence when a district court denied a defendant’s request for “more time” and implied to the defendant that it preferred a guilty plea). The primary purpose of this bright-line rule is to “diminish[] the possibility of judicial coercion of a guilty plea, regardless whether the coercion would actually result in an involuntary guilty plea.” Id. (citation omitted); see also United States v. Hemphill, 748 F.3d 666, 676 (5th Cir.2014) (“[Ojnce a court has exerted pressure on a defendant [to accept a plea] it is difficult, if not impossible, to undo the coercive effects of that pressure.”); United States v. Ayika, 554 Fed.Appx. 302, 309 (5th Cir. 2014) (noting that judicial involvement in a defendant’s decision to plead guilty “makes it difficult for a judge to objectively assess the voluntariness of the plea” (quoting Fed. R. CRiM.' P. 11 advisory committee’s notes (1974))).
In this case, Reggie moved to withdraw his guilty plea and thereafter testified that his medical condition and the district court’s e-mail resulted in feeling coerced to plead guilty.6 Cf. Hemphill, 748 F.3d at 674, 675 (noting that the district court’s actions, “done with even the best of intentions, simply went too far” because they “tended to exert pressure on [the defendant] ... even if such belief was only in [the defendant’s] mind”). While we need not and do not address whether the district court’s e-mail was a violation of Rule 11(c)(1)’s prohibition on a district court’s participation on plea negotiations, the effect of the district court’s e-mail on Reggie further underscores the need to comply scrupulously with Rule 11(b)(2)’s requirements in this case. See Henry, 113 F.3d at 41.
The combination of these unique and unusual circumstances — Reggie’s recent stroke and its impact on his ability to assist in his own defense, the denial of the continuance of the trial, and the e-mail notifying Reggie that if he did not plead guilty, the trial would begin — convince us that the Government has not met its burden to show that the Rule 11(b)(2) error [251]*251was harmless.7 See Vonn, 535 U.S. at 62, 122 S.Ct. 1043. If the district court had engaged in a proper plea colloquy regarding voluntariness, Reggie would have had the opportunity to tell the court that he felt coerced into pleading guilty due to his health condition and the imminent trial. Therefore, there was at least a “reasonable probability” that, had Reggie provided this information after a proper Rule 11(b)(2) colloquy, the district court would not have accepted his guilty plea. See Hemphill, 748 F.3d at 677. The district court’s flawed compliance with Rule 11 could reasonably be viewed as a material factor affecting Reggie’s decision to plead guilty, and thus was not harmless error. See Johnson, 1 F.3d at 302.
For the foregoing reasons, we VACATE the district court’s acceptance of Reggie’s guilty plea, the conviction, and sentence. We REMAND for further proceedings.8
Pursuant to 5th Cir. R. 47.5, the court has determined that this opinion should not be published and is not precedent except under the limited circumstances set forth in 5th Cm. R. 47.5.4.