Opinion by Judge GOULD; Dissent by Judge BERZON.
GOULD, Circuit Judge.
We consider whether a plea agreement is enforceable and effectively waives the right of appeal. We conclude that we are without jurisdiction to assess the merits of this direct appeal.
I
In July 2002, Pascual Dionicio Jeronimo (“Jeronimo”) faced a potential maximum sentence of thirty years imprisonment for various drug trafficking offenses when he entered into plea negotiations with the government. Through his former attorney, John Kolego (“Kolego”), Jeronimo reached a plea agreement on November 1, 2002, whereby the government agreed to dismiss some of his pending charges, recommend downward departure and a sentence at the low end of the applicable guideline range, refrain from seeking an upward departure, and reduce his maximum potential sentence to twenty years. In return, Jeronimo agreed to plead guilty to two counts of drug trafficking, admit to specific drug quantities, forfeit his interest in certain property, and to waive his rights to appeal and to collaterally attack the length of his sentence. Both Jeronimo and Kolego signed the plea agreement. Immediately above Jeronimo’s signature in capital letters was the following statement:
[1151]*1151I HAVE READ OR HAD READ AND TRANSLATED TO ME IN SPANISH BY AN INTERPRETER, THIS AGREEMENT AND HAVE CAREFULLY REVIEWED EVERY PART OF IT WITH MY ATTORNEY.
I UNDERSTAND AND VOLUNTARILY AGREE TO IT AND PROMISE TO ABIDE BY EVERY TERM.
I VOLUNTARILY SIGN THIS AGREEMENT WITH THE FULL UNDERSTANDING OF ALL OF THE ABOVE.
At Jeronimo’s change of plea hearing, which also took place on November 1, 2002, the district court dutifully conducted a comprehensive plea colloquy with Jeroni-mo that embraced all disclosures and inquiries required by Rule 11 of the Federal Rules of Criminal Procedure.1 Among these disclosures was the district court’s explicit advice to Jeronimo that “the maximum penalty [under his plea agreement was] 20 years in prison and a fine of up to $1 million.” Jeronimo in response assured the district court that he had discussed the federal Sentencing Guidelines with Kolego, and that he was satisfied with Kolego’s help. When asked if his plea was “freely and voluntarily made with a good understanding of the nature of the charges against [him] and the matters in [the] plea petition and plea bargain letter,” Jeronimo, said “yes.”
Before the court’s acceptance of the plea, the prosecutor interjected comments alerting Jeronimo that the government was planning to bring .his prior drug and felony assault convictions, as well as his status as an illegal alien and a prison [1152]*1152escapee, to the court’s attention during sentencing. When the court asked Jeroni-mo if he understood that these facts would “likely affect [his] sentence,” Jeronimo responded “yes.” The court accepted his plea.
The United States Probation Office issued its Presentence Report and Sentencing Recommendation on December 10, 2002. Because of his previous convictions for felony assault and drug trafficking, Jeronimo was classified as a career offender with an applicable Sentencing Guidelines range of 151-88 months of imprisonment.
On March 6, 2003, Jeronimo moved through Kolego to withdraw his guilty plea on the grounds that “he[did] not believe that he was adequately advised as to the potential sentencing consequences prior to his change of plea and[did] not feel his plea was intelligently and knowingly made.” On March 17, 2003, Jeronimo filed a separate pro se “Motion to Withdraw Plea of Guilty Due to Inadequate and Fraudulent Representation By Legal Counsel” alleging that Kolego “on several occasions distorted facts as well as misled for the purpose of extracting a ‘Guilty’ plea.” He also alleged that Kolego “repeatedly changed and lied about possible sentences after [the] plea of ‘Guilty’ was entered.”
On May 27, 2003, Richard Fredericks (“Fredericks”) was appointed as Jeroni-mo’s new attorney. On August 14, 2003, Fredericks filed a Memorandum in Support of Motion to Withdraw Guilty Plea on Jeronimo’s behalf, asserting that Jeronimo was “deprived ... of the opportunity to make an intelligent and voluntary decision” because he allegedly pleaded in reliance on Kolego’s erroneous prediction that he would receive a sentence of 87 months.
At a hearing on his plea withdrawal motion, Jeronimo testified that he had many discussions with Kolego about “the merits of the plea offer” and the Sentencing Guidelines, and that his “understanding” based on these discussions was that he would receive a sentence of 87 months as Kolego “prediet[ed].” Jeronimo also testified that Kolego never raised the possibility of “career offender” sentencing during any of their discussions and that he would not have accepted the plea offer if he had known that he would receive a sentence of 151 months.
On cross-examination, Jeronimo continued to assert that he had “made a deal” with Kolego, stating: “I trusted in him ... and I signed for 87 months. When I realized that the sentence was longer, if I had realized, if I known that, I wouldn’t have sign[ed] it.” However, he conceded that he entered his plea with the understanding that his sentencing would be up to the judge, not Kolego. Jeronimo also admitted that “the deal that [he] made with his lawyer did not include what this judge was going to sentence [him] to”; that the government had warned him at his change of plea hearing that his prior convictions would be raised at sentencing, and the district court had observed that those facts would “likely affect the extent” of his sentence; that he had pleaded guilty with the understanding that he could receive a sentence of up to twenty years; and that he had received the benefit of his bargain because 151 months was less than twenty years.
In denying Jeronimo’s motion to withdraw his plea, the district court noted that Jeronimo’s argument that his defense attorney “blew the career offender issue” was “made without evidence from the attorney,” and that “even if that was the case ... a perfect attorney doesn’t exist.” This timely appeal followed.
II
We lack jurisdiction to entertain appeals where there was a valid and en[1153]*1153forceable waiver of the right to appeal. United States v. Vences, 169 F.3d 611, 613 (9th Cir.1999) (“It would overreach our jurisdiction to entertain an appeal when the plea agreement effectively deprived us of jurisdiction.”). We review de novo whether a defendant has waived his right to appeal by entering into a plea agreement and the validity of such a waiver. United States v. Ventre, 338 F.3d 1047, 1051 (9th Cir.2003). A defendant’s waiver of his appellate rights is enforceable if (1) the language of the waiver encompasses his right to appeal on the grounds raised, and (2) the waiver is knowingly and voluntarily made. United States v. Joyce, 357 F.3d 921, 922 (9th Cir.2004); United States v. Martinez, 143 F.3d 1266, 1270-71 (9th Cir.1998).
A
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Opinion by Judge GOULD; Dissent by Judge BERZON.
GOULD, Circuit Judge.
We consider whether a plea agreement is enforceable and effectively waives the right of appeal. We conclude that we are without jurisdiction to assess the merits of this direct appeal.
I
In July 2002, Pascual Dionicio Jeronimo (“Jeronimo”) faced a potential maximum sentence of thirty years imprisonment for various drug trafficking offenses when he entered into plea negotiations with the government. Through his former attorney, John Kolego (“Kolego”), Jeronimo reached a plea agreement on November 1, 2002, whereby the government agreed to dismiss some of his pending charges, recommend downward departure and a sentence at the low end of the applicable guideline range, refrain from seeking an upward departure, and reduce his maximum potential sentence to twenty years. In return, Jeronimo agreed to plead guilty to two counts of drug trafficking, admit to specific drug quantities, forfeit his interest in certain property, and to waive his rights to appeal and to collaterally attack the length of his sentence. Both Jeronimo and Kolego signed the plea agreement. Immediately above Jeronimo’s signature in capital letters was the following statement:
[1151]*1151I HAVE READ OR HAD READ AND TRANSLATED TO ME IN SPANISH BY AN INTERPRETER, THIS AGREEMENT AND HAVE CAREFULLY REVIEWED EVERY PART OF IT WITH MY ATTORNEY.
I UNDERSTAND AND VOLUNTARILY AGREE TO IT AND PROMISE TO ABIDE BY EVERY TERM.
I VOLUNTARILY SIGN THIS AGREEMENT WITH THE FULL UNDERSTANDING OF ALL OF THE ABOVE.
At Jeronimo’s change of plea hearing, which also took place on November 1, 2002, the district court dutifully conducted a comprehensive plea colloquy with Jeroni-mo that embraced all disclosures and inquiries required by Rule 11 of the Federal Rules of Criminal Procedure.1 Among these disclosures was the district court’s explicit advice to Jeronimo that “the maximum penalty [under his plea agreement was] 20 years in prison and a fine of up to $1 million.” Jeronimo in response assured the district court that he had discussed the federal Sentencing Guidelines with Kolego, and that he was satisfied with Kolego’s help. When asked if his plea was “freely and voluntarily made with a good understanding of the nature of the charges against [him] and the matters in [the] plea petition and plea bargain letter,” Jeronimo, said “yes.”
Before the court’s acceptance of the plea, the prosecutor interjected comments alerting Jeronimo that the government was planning to bring .his prior drug and felony assault convictions, as well as his status as an illegal alien and a prison [1152]*1152escapee, to the court’s attention during sentencing. When the court asked Jeroni-mo if he understood that these facts would “likely affect [his] sentence,” Jeronimo responded “yes.” The court accepted his plea.
The United States Probation Office issued its Presentence Report and Sentencing Recommendation on December 10, 2002. Because of his previous convictions for felony assault and drug trafficking, Jeronimo was classified as a career offender with an applicable Sentencing Guidelines range of 151-88 months of imprisonment.
On March 6, 2003, Jeronimo moved through Kolego to withdraw his guilty plea on the grounds that “he[did] not believe that he was adequately advised as to the potential sentencing consequences prior to his change of plea and[did] not feel his plea was intelligently and knowingly made.” On March 17, 2003, Jeronimo filed a separate pro se “Motion to Withdraw Plea of Guilty Due to Inadequate and Fraudulent Representation By Legal Counsel” alleging that Kolego “on several occasions distorted facts as well as misled for the purpose of extracting a ‘Guilty’ plea.” He also alleged that Kolego “repeatedly changed and lied about possible sentences after [the] plea of ‘Guilty’ was entered.”
On May 27, 2003, Richard Fredericks (“Fredericks”) was appointed as Jeroni-mo’s new attorney. On August 14, 2003, Fredericks filed a Memorandum in Support of Motion to Withdraw Guilty Plea on Jeronimo’s behalf, asserting that Jeronimo was “deprived ... of the opportunity to make an intelligent and voluntary decision” because he allegedly pleaded in reliance on Kolego’s erroneous prediction that he would receive a sentence of 87 months.
At a hearing on his plea withdrawal motion, Jeronimo testified that he had many discussions with Kolego about “the merits of the plea offer” and the Sentencing Guidelines, and that his “understanding” based on these discussions was that he would receive a sentence of 87 months as Kolego “prediet[ed].” Jeronimo also testified that Kolego never raised the possibility of “career offender” sentencing during any of their discussions and that he would not have accepted the plea offer if he had known that he would receive a sentence of 151 months.
On cross-examination, Jeronimo continued to assert that he had “made a deal” with Kolego, stating: “I trusted in him ... and I signed for 87 months. When I realized that the sentence was longer, if I had realized, if I known that, I wouldn’t have sign[ed] it.” However, he conceded that he entered his plea with the understanding that his sentencing would be up to the judge, not Kolego. Jeronimo also admitted that “the deal that [he] made with his lawyer did not include what this judge was going to sentence [him] to”; that the government had warned him at his change of plea hearing that his prior convictions would be raised at sentencing, and the district court had observed that those facts would “likely affect the extent” of his sentence; that he had pleaded guilty with the understanding that he could receive a sentence of up to twenty years; and that he had received the benefit of his bargain because 151 months was less than twenty years.
In denying Jeronimo’s motion to withdraw his plea, the district court noted that Jeronimo’s argument that his defense attorney “blew the career offender issue” was “made without evidence from the attorney,” and that “even if that was the case ... a perfect attorney doesn’t exist.” This timely appeal followed.
II
We lack jurisdiction to entertain appeals where there was a valid and en[1153]*1153forceable waiver of the right to appeal. United States v. Vences, 169 F.3d 611, 613 (9th Cir.1999) (“It would overreach our jurisdiction to entertain an appeal when the plea agreement effectively deprived us of jurisdiction.”). We review de novo whether a defendant has waived his right to appeal by entering into a plea agreement and the validity of such a waiver. United States v. Ventre, 338 F.3d 1047, 1051 (9th Cir.2003). A defendant’s waiver of his appellate rights is enforceable if (1) the language of the waiver encompasses his right to appeal on the grounds raised, and (2) the waiver is knowingly and voluntarily made. United States v. Joyce, 357 F.3d 921, 922 (9th Cir.2004); United States v. Martinez, 143 F.3d 1266, 1270-71 (9th Cir.1998).
A
We first must address the issue of whether Jeronimo’s waiver of his right to appeal precludes his challenge on direct appeal to the district court’s rejection of his request to withdraw his guilty plea, based on his assertion that fair and just reasons supported a change of plea. “Our analysis begins with the fundamental rule that plea agreements are contractual in nature and are measured by contract law standards.” United States v. Clark, 218 F.3d 1092, 1095 (9th Cir.2000) (internal citation and quotation marks omitted). This customary reliance on contract law applies to interpretation of an appeals waiver within a plea agreement, and we will generally enforce the plain language of a plea agreement if it is clear and unambiguous on its face. United States v. Nunez, 223 F.3d 956, 958 (9th Cir.2000); see also Martinez, 143 F.3d at 1271.
In Martinez, the defendant entered into a plea agreement with language similar to that here. The Martinez plea agreement provided that “[a]ny plea of guilty entered by Defendant pursuant to this agreement and any judgment and/ or sentence based thereon ... will not be the subject of legal challenge by Defendant.” 143 F.3d at 1270. In rejecting the defendant’s attempt to appeal his sentence on the grounds that the district court had misapplied the Sentencing Guidelines, we held that the defendant’s “waiver of any ‘legal challenge’ encompasses all appeals on all grounds except for a few narrow exceptions,2 none of which apply here.” Id. at 1271. Similarly, in Nunez we held that an agreement stating that the defendant “knowingly and voluntarily waive[s] his right to appeal any sentence imposed by the Court” constituted an “unmistakable” waiver of the right to appeal. 223 F.3d at 958 (internal quotation marks omitted).
Here, Jeronimo’s agreement provides in pertinent part that:
[1154]*1154By accepting the benefits of this agreement and if sentenced by the Court to a term of imprisonment of less than the statutory maximum of 20 years, Mr. Jer-onimo waives any and all rights to appeal, and all his waivable statutory rights to file a petition pursuant to 28 U.S.C. § 2255 challenging the length of his sentence.
This language plainly states that Jeronimo waived his right to appeal his sentence on any and all grounds in exchange for a sentence of less than twenty years and various other benefits under the agreement. Thus, based on Martinez and Nunez, we conclude that Jeronimo’s plea agreement clearly encompasses his right to bring the present appeal.
Jeronimo contends that the waiver language only covers his right to appeal on the grounds that his sentence was improper or violated the terms of the plea agreement; he argues that we have jurisdiction because the waiver does not specifically preclude him from appealing on the grounds that the district court abused its discretion. However, we dismissed a similar argument in United States v. Schuman, 127 F.3d 815, 817 (9th Cir.1997), where the appellant asserted that a plea agreement providing that he “waive[d] ... any right to appeal or collaterally attack the conviction and sentence” did not preclude him from challenging the district court’s application of the federal Sentencing Guidelines because the agreement failed to “specifically address his statutory right to appeal” on that basis. There we stated: “We reject [the appellant’s] contention that the language of the plea agreement does not specifically contemplate the statutory right to appeal incorrect applications of the Sentencing Guidelines for it would render the waiver meaningless.” Id. Accordingly, while Jeronimo’s plea agreement does not specifically contemplate the possibility of an appeal based on the district court’s denial of a motion to withdraw, its broad language clearly bars him from bringing this appeal.
B
Having concluded that Jeronimo’s waiver included the appeal he now advances, we next consider whether his waiver was knowing and voluntary. We follow the rule that a waiver of the right to appeal is knowing and voluntary where the plea agreement as a whole was knowingly and voluntarily made. As we stated in Portillo-Cano:
[WJaivers of appeal must stand or fall with the agreement of which they are a part. If the agreement is voluntary, and taken in compliance with Rule 11, then the waiver of appeal must be honored. If the agreement is involuntary or otherwise unenforceable, then the defendant is entitled to appeal.
192 F.3d at 1250 (internal quotation marks and citation omitted).
At least on its face, the district court’s extensive Rule 11 colloquy with Jeronimo shows that Jeronimo’s plea was knowingly and voluntarily made. The district court properly advised Jeronimo of the nature of the drug charges against him, the consequences of conviction, and the constitutional rights he was waiving by pleading guilty. The district court also summarized each of the terms of Jeronimo’s plea agreement, including the appeal waiver provision, and informed Jeronimo that his maximum possible penalty under the agreement was 20 years imprisonment and a fine of $1 million. Noting that the government would bring “relevant facts” to its attention, the district court further advised Jeronimo that it could depart from the applicable Sentencing Guidelines ranges for various reasons and told him not to rely on sentencing predictions made by others because “the judge decides the sentence.”
[1155]*1155Jeronimo responded by acknowledging that he had discussed the Sentencing Guidelines with Kolego, and assuring the district court that his plea was “freely and voluntarily made.” Finally, when the government warned that it would raise Jeroni-mo’s prior convictions and status as an illegal alien and prison escapee at sentencing, the district court asked Jeronimo if he understood that such facts would “likely affect [his] sentence,” and Jeronimo said “yes.”
Nonetheless, Jeronimo claims that his attorney’s failure to advise him of all the possible consequences of a guilty plea deprived him of the information necessary to render his plea — and the waiver of appeal contained therein — truly knowing and voluntary.3
To demonstrate ineffective assistance of counsel, a defendant must show: (1) that his counsel’s performance was deficient;. and (2) that the deficient performance prejudiced his defense. Strickland v. Washington, 466 U.S. 668, 687, 104 S.Ct. 2052, 80 L.Ed.2d 674 (1984). This test applies to challenges to guilty pleas based on ineffective assistance of counsel claims. Hill v. Lockhart, 474 U.S. 52, 58, 106 S.Ct. 366, 88 L.Ed.2d 203 (1985).
We first consider whether counsel Kolego’s performance is shown to be deficient on the record before us. “A defendant who pleads guilty upon the advice of counsel may only attack the voluntary and intelligent character of his guilty plea by showing that the advice he received from counsel was not within the range of competence demanded of attorneys in criminal cases.” United States v. Signori, 844 F.2d 635, 638 (9th Cir.1988). Because of the difficulties in evaluating attorney performance in hindsight, courts considering ineffective counsel claims “indulge a strong presumption that counsel’s conduct falls within the wide range of reasonable professional assistance.” Strickland, 466 U.S. at 689, 104 S.Ct. 2052.
Here, the main thrust of Jeronimo’s ineffective assistance of counsel claim is that his attorney’s failure to consider and inform him of the possibility that he might be sentenced as a career offender constituted a “misrepresentation” that justifies withdrawal of his plea.
A guilty plea cannot be “induced by ... misrepresentation.” Signori, 844 F.2d at 638 (quoting Brady v. United States, 397 U.S. 742, 755, 90 S.Ct. 1463, 25 L.Ed.2d 747 (1970)). We have also held that a defendant who pleads guilty in reliance on his or her attorney’s “gross mischaraeteri-zation of the likely outcome” of his or her case may be entitled to withdraw the plea on ineffective assistance of counsel grounds. Iaea v. Sunn, 800 F.2d 861, 865 (9th Cir.1986); see also U.S. v. Michlin, 34 F.3d 896, 899 (9th Cir.1994) (“We have held that an erroneous prediction by a defense attorney concerning sentencing does not entitle a defendant to challenge his guilty plea, although an exception might be made in a case of gross mischar-acterization of the likely outcome.”) (internal quotation marks and citations omitted).
However, as a general rule, we do not review challenges to the effectiveness of defense counsel on direct appeal. United States v. McKenna, 327 F.3d 830, 845 (9th Cir.2003). Thus, in McKenna, we declined to review an ineffective assistance of counsel claim on direct appeal because we concluded, inter alia, that we could not evaluate the defendant’s claim that counsel should have filed various motions because the “record [wa]s ... not developed with respect to why [the defendant’s] attorneys [1156]*1156felt that the motionsfthe defendant] wanted filed were not warranted by the evidence.” Id.
To similar effect i's our decision in United States v. Laughlin, 933 F.2d 786, 788-89 (9th Cir.1991), where a defendant whose probation was revoked brought an ineffective assistance claim on direct appeal and contended that his counsel’s performance during his revocation hearing was so constitutionally deficient as to merit a new hearing. We declined to address the defendant’s claim because “[t]he record contained] little more than generalized assertions of incompetency.” Id. at 789. We stressed that “[flormer defense counsel has had no opportunity to explain his actions” and that the defendant had not “established any foundation for demonstrating that the alleged errors actually prejudiced the outcome of the hearing.” Id.
The rationale for our general rule, as explained in United States v. Birges, 723 F.2d 666, 670 (9th Cir.1984), is that ineffectiveness of counsel claims “usually ... cannot be advanced without the development of facts outside the original record.” Stated another way, a “[c]hallenge [to effectiveness of counsel] by way of a habeas corpus proceeding is preferable as it permits the defendant to develop a record as to what counsel did, why it was done, and what, if any, prejudice resulted.” Laughlin,, 933 F.2d at 788-89.
We have recognized two extraordinary exceptions to this general rule: We have permitted ineffective assistance claims to be reviewed on direct appeal in the unusual cases (1) where the record on appeal is sufficiently developed to permit determination of the issue, or (2) where the legal representation is so inadequate that it obviously denies a defendant his Sixth Amendment right to counsel. United States v. Daychild, 357 F.3d 1082, 1095 (9th Cir.2004).
In these exceptional cases, the reason for our general rule is inapplicable because development of further evidence is unnecessary to assess whether counsel performed below the constitutionally required standard. See, e.g., United States v. Anderson, 850 F.2d 563, 565 n. 1 (9th Cir.1988). But neither of these exceptions apply here; as Jeronimo points out, the record contains no evidence from Kolego. Contrary to the dissent’s argument, we do not suggest that evidence from Kolego is required because he might have made a “strategic decision” not to inform Jeronimo about the career offender issue. Rather, such evidence is necessary because, on the current state of the record, we cannot determine whether Kolego in fact failed to inform Jeronimo about that issue at all. Jeronimo cannot, at this stage on direct appeal, make out an ineffective assistance claim.
In light of the scope of the record on this direct appeal, we cannot now conclude that Jeronimo has shown that his plea agreement, which included an unequivocal waiver of his appeal rights, was involuntary and unenforceable. Further, “we will not remand a case from direct appeal for fact-finding related to an ineffective assistance of counsel claim, but allow a defendant to pursue the issue in district court collateral proceedings.” United States v. Reyes-Platero, 224 F.3d 1112, 1117 (9th Cir.2000).4
[1157]*1157III
We lack jurisdiction to entertain this appeal because the appeal waiver in Jeron-imo’s plea agreement is unambiguous and the record as it is currently constituted demonstrate that the agreement was no^ knowingly and voluntarily made.5
APPEAL DISMISSED.