Francisco Alonso Portillo-Cano ("Portillo-Cano" or "defendant") appeals his guilty plea entered before the district court on the ground that his plea did not conform to the requirements of Rule 11(c) of the Federal Rules of Criminal Procedure. The government asserts that defendant is barred from appealing his sentence because his plea agreement included a waiver of his right to appeal. We hold that we may hear defendant's appeal in order to determine whether his guilty plea failed to comply with the requirements of Rule 11 because the trial Judge did not explain the nature of the charges. We also hold that the plea colloquy at issue did not conform to Rule 11. We have jurisdiction under 28 U.S.C. S 1291 (1994) and we vacate and remand for further proceedings.

In June 1996, Portillo-Cano was indicted by a grand jury on four counts: Count 1 that he conspired to possess with intent to distribute marijuana, in violation of 21 U.S.C.S 841(a)(1) (1994); Count 2 that he possessed with intent to distribute, and aided, abetted... or induced... others to possess with intent to distribute marijuana, in violation of 21 U.S.C. S 841(a)(1) and 18 U.S.C. S 2 (1994); and, Counts 3 and 4, that he used and carried a firearm during and in relation to a drug trafficking crime, in violation of 18 U.S.C.S 924(c) (1994).

In 1995, Portillo-Cano negotiated with a confidential informant ("CI") who worked for the U.S. Customs Service. On March 28, 1995, Portillo-Cano gave the CI a two-ounce sample of marijuana. One week later, Portillo-Cano told the CI that a large quantity of marijuana was available right away. Portillo-Cano brought the CI to a residence in Tucson, Arizona where the CI observed a large quantity of marijuana at the premises. Two men wereguarding the marijuana, one of whom was holding a handgun. A federal search of the residence led to the seizure of 1,160 pounds of marijuana and two firearms.

Pursuant to a Rule 11(e)(1)(C) plea agreement, Portillo-Cano entered a change of plea and pled guilty to Counts 1 and 4 of the indictment on May 28, 1997. Upon entering into an enforceable Rule 11(e)(1)(C) agreement, Portillo-Cano would have waived his right to appeal a sentence called for by the agreement.1 The plea agreement included a provision that Portillo-Cano understood he was giving up his right to appeal the sentence. Portillo-Cano also was to forfeit all right and title to the two firearms. The district court sentenced defendant on March 31, 1998 to 60 months for Count 1, and 11 months for Count 4, to run consecutively.2

Defendant appealed his conviction and sentence to this court on April 8, 1998. Portillo-Cano claims that in the plea allocution of May 28, 1997 the district court Judge failed to comply with the requirement of Fed. R. Crim. P. 11(c)(1) that the Judge explain, in open court, the nature of the charges brought against the defendant.

We review the validity of a defendant's waiver of the right to appeal de novo. United States v. Buchanan, 59 F.3d 914, 916 (9th Cir. 1995). We also review de novo whether a trial court's colloquy with a defendant satisfies the requirements of Rule 11(c)(1) of the Federal Rules of Criminal Procedure. United States v. Smith, 60 F.3d 595, 597 n.1 (9th Cir. 1995).

The government's only argument on appeal is that Portillo-Cano waived his right to appeal his sentence in his plea agreement. A defendant has a statutory right to appeal his criminal sentence. See 18 U.S.C. S 3742(a)(1). This right, however, may be waived if the defendant knowingly and voluntarily agrees to the waiver. United States v. NavarroBotello, 912 F.2d 318, 321 (9th Cir. 1990) (holding that waiver of right to appeal as part of negotiated plea agreement does not violate due process or public policy). Nevertheless, in Navarro-Botello we also looked at the quality of the Rule 11(c) colloquy to ascertain that the defendant's waiver was knowingly and voluntarily made. See id. (prior to addressing waiver of right to appeal, court reviewed record and found Rule 11 requirements satisfied).

We recognize that a defendant who has waived the right to appeal may still appeal a criminal sentence under certain circumstances. See United States v. Schuman, 127 F.3d 815, 818 n.* (9th Cir. 1997) (Kozinski, J., Concurring) (reviewing cases in which defendant may appeal sentence in spite of waiver). For instance, a waiver of a right to appeal if the sentence violates the law or is based on "an incorrect application of the sentencing guidelines." United States v. Littlefield, 105 F.3d 527, 528 (9th Cir.)(per curiam) (interpreting waiver of right to appeal pursuant to a Rule 11(e)(1)(C) agreement), cert. Denied 520 U.S. 1258, 117 S. Ct. 2423, 138 L. Ed. 2d 186 (1997).

The cases cited by the Government in support of its argument that the right to appeal was waived validly do not involve situations where the defendant challenged compliance with the Rule 11(c) procedure. In Schuman, the court dismissed the appeal on the grounds that the waiver in the plea agreement was expressly stated, and that statements by the district court judgethat the defendant may still have had some rights to appeal did not give rise to a contrary result because the prosecution objected to this advisement by the court. Schuman, 127 F.3d at 817. The court also rejected Schuman's contention that the Government had failed to comply with the plea agreement. Id. Buchanan, also cited by the Government, stands for the proposition that, generally, when the district court Judge tells the defendant he may have a right to appeal, that "oral pronouncement must control," because the defendant "could have a reasonable expectation" that he could appeal his sentence. Buchanan, 59 F.3d at 917. In neither of these cases was the defendant denied the right to appeal a sentence even though compliance with the procedural requirements of Rule 11(c) was at issue.

As stated by the Seventh Circuit, waivers of appeal must "stand or fall with the agreement of which they are a part." United States v. Wenger, 58 F.3d 280, 282 (7th Cir. 1995). "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. " Id.

Portillo-Cano is challenging the soundness of his plea allocution under Rule 11, which goes to the heart of whether his guilty plea, including the waiver of appeal, is enforceable. Thus, we must determine whether the plea was valid in order to determine if appeal is permitted.

Our holding in United States v. Vences, 169 F.3d 611 (9th Cir. 1999), is not to the contrary. In Vences, we held that we lacked jurisdiction on appeal where the defendant waived the right to appeal in his plea agreement, even though the trial Judge failed to explain the reasons for imposing the sentence, as required by 18 U.S.C. S 3553 (1994). The trial Judge's failure to comply with 18 U.S.C. S 3553 did not make the sentence illegal, 169 F.2d at 613, and did not implicate the voluntariness of the defendant's plea. By contrast, compliance with Rule 11 is the means by which the court is assured that the defendant's guilty plea is voluntarily and knowingly made.

Rule 11(c)(1) of the Federal Rules of Criminal Procedure requires that before accepting a plea of guilty, the "court must address the defendant personally in open court and inform the defendant of, and determine that the defendant understands, the following: (1) the nature of the charge to which the plea is offered [and the mandatory minimum penalty and maximum possible penalty]." The purpose of Rule 11 is to "ensure that guilty pleas are knowing and voluntary." United States v. Longoria, 113 F.3d 975, 977 (9th Cir. 1997) ("defendant's right to be informed of the charges against him is at the core of Rule 11.").

In reviewing the compliance of a plea with Rule 11(c), we review only the record of the plea proceeding. United States v. Jaramillo-Suarez, 857 F.2d 1368, 1372-73 (9th Cir. 1988) (quoting United States v. Kamer, 781 F.2d 1380, 1383 (9th Cir. 1986)). We are therefore confined to analyzing the transcript of the Discussion between the trial Judge and Portillo-Cano on May 28, 1997. Upon review we conclude that the trial Judge failed in only one respect with regard to the requirements of Rule 11. He did not explain the nature of the charges for which Portillo-Cano was indicted.

As stated in Smith, failure to explain the nature of the charge "requires the vacation of a plea of guilty." 60 F.3d at 597 (citing United States v. Bruce, 976 F.2d 552, 559-60 (9th Cir. 1992)).3 Theplea colloquy in Smith was similar to, and clearly no more deficient than, the one at issue in this case. In Smith the defense attorney waived the reading of the indictment, but this waiver did not "excuse the omission" by the trial court. Id. at 597.4

In Smith the Government argued that other events at the plea hearing showed that the defendant understood the nature of the charges brought against him, and that the district court had complied with all of the remaining requirements of Rule 11(c). Id. The prosecutor in Smith established the factual basis for the plea, and the defendant admitted all of those facts. We held that "[w]hile these recitations may satisfy other requirements of Rule 11(c), they do not convey to Smith the nature of the charges against him.... [A]n admission of the facts does not speak to the nature of the charge." Id. at 597. We held that a guilty plea cannot be truly voluntary unless the defendant "possesses an understanding of the law in relation to the facts." Id. (quoting McCarthy v. United States, 394 U.S. 459, 466 (1969)).

A statement by the defendant and his attorney that they discussed the nature of the charge is also insufficient to satisfy Rule 11(c), because "vague references to Discussion of `the charges' and `the nature of the charges' does not provide a complete record showing compliance with Rule 11(c)." Smith, 60 F.3d at 598.5 Smith also held that a provision in the plea agreement stating the acts the defendant must have committed in order to be found guilty of the crime charged cannot cure the failure to describe the nature of the charges in open court where that provision of the plea agreement was not "recited or even referred to in the plea proceeding." Smith, 60 F.3d at 599. Likewise, in Portillo-Cano's plea proceeding no mention was made of what acts he must have committed in order to be found guilty of either charge, and the plea agreement also did not contain such statements. Furthermore, assurances that at some point outside of the plea agreement the defendant was informed of the nature of the charge cannot cure the Judge's failure to do so in open court. Smith, 60 F.3d at 599 (quoting United States v. Kennell, 15 F.3d 134, 136 (9th Cir. 1994) ("reading of the plea agreement is no substitute for rigid observance of Rule 11.")).

Smith also establishes that the failure to identify the nature of the charges is not harmless error pursuant to Rule 11(h). The omission to identify and explain the crime is "fundamental." Smith, 60 F.3d at 599. We recently held that "[a]ny deviation from the requirements of Rule 11 is reversible unless the government demonstrates that it was `harmless.' " United States v. Odedo, 154 F.3d 937, 940 (9th Cir. 1998) (quoting United States v. Lyons, 53 F.3d 1321, 1322 n.1 (D.C. Cir. 1995)).6 In the absence of "anyreference at the plea hearing to the charge or its nature, we can assume nothing more than total ignorance of the charge on the part of [the defendant]." Smith, 60 F.3d at 600.

The trial Judge in this case did identify the two crimes: conspiracy and use of a firearm during a drug trafficking crime.

The Judge did not, however, discuss the elements of these crimes in order to demonstrate on the record that the defendant understood the nature of the charges. See Kamer, 781 F.2d at 1384 (failure to read indictment and explain nature of offense violated Rule 11) (citing Irizarry v. United States, 508 F.2d 960, 965-66 (2d Cir. 1974) ("trial Judge should at least set out the bare bones elements of the offense.")).

Because Portillo-Cano's plea allocution did not include a description of the nature of the charges, including an application of the law to the facts, we find that this plea did not conform to the requirements of Fed. R. Crim. P. 11(c)(1) and that defendant's right to appeal was not waived. Accordingly, we VACATE the conviction and REMAND for further proceedings consistent with this opinion.