UNITED STATES COURT OF APPEALS 

FOR THE TENTH CIRCUIT 

_________________________________ 

KENNETH L. KIRKLAND, 

 Petitioner - Appellant, 

v. 

N.C. ENGLISH, 

 Respondent - Appellee. 

No. 18-3175 

(D.C. No. 5:18-CV-03186-JWL) 

(D. Kan.) 

_________________________________ 

ORDER AND JUDGMENT*

_________________________________ 

Before HOLMES, MATHESON, and EID, Circuit Judges. 

_________________________________ 

Proceeding pro se, federal prisoner Kenneth Kirkland appeals the district 

court’s denial of his 28 U.S.C. § 2241 habeas application—his third attempt at habeas 

relief and second under § 2241.1

 The district court dismissed Mr. Kirkland’s 

application because it should have been brought under 28 U.S.C. § 2255 and did not 

 * After examining the briefs and appellate record, this panel has determined 

unanimously that oral argument would not materially assist in the determination of 

this appeal. See Fed. R. App. P. 34(a)(2); 10th Cir. R. 34.1(G). The case is therefore 

ordered submitted without oral argument. This order and judgment is not binding 

precedent, except under the doctrines of law of the case, res judicata, and collateral 

estoppel. It may be cited, however, for its persuasive value consistent with 

Fed. R. App. P. 32.1 and 10th Cir. R. 32.1. 

1

 Mr. Kirkland requests a certificate of appealability, Aplt. Br. at 6-7, but a 

federal prisoner is not required to obtain one to seek review of a district court’s 

denial of a habeas application under § 2241, Eldridge v. Berkebile, 791 F.3d 1239, 

1243 (10th Cir. 2015). 

FILED 

United States Court of Appeals 

Tenth Circuit 

November 30, 2018

Elisabeth A. Shumaker 

Clerk of Court
2 

qualify for the exception in § 2255(e)’s savings clause. Exercising jurisdiction under 

28 U.S.C. § 1291, we affirm. 

I. BACKGROUND 

In 2008, Mr. Kirkland was convicted in the United States District Court for the 

Southern District of Illinois of intent to distribute cocaine base in violation of 

21 U.S.C. § 841(a)(1). United States v. Kirkland, No. 3:07-cr-30137-MJ-DGW, 

(S.D. Ill. Sept. 19, 2008). He was sentenced to 240 months in prison. Id. Mr. 

Kirkland received a longer sentence because he had a prior felony drug offense under 

21 U.S.C. § 841. In his brief, he reports this predicate offense was for second-degree 

drug trafficking under Missouri law. Aplt. Br. at 1. Mr. Kirkland is serving his 

sentence at a federal prison in Kansas. 

Mr. Kirkland appealed his conviction to the Seventh Circuit, arguing that: 

(1) the police held him for an unreasonable period of time before bringing him before 

a magistrate, and (2) the district court erred in failing to suppress his confession. See 

United States v. Kirkland, 567 F.3d 316, 318-19 (7th Cir. 2009). The Seventh Circuit 

affirmed. Id. at 322. The Supreme Court denied certiorari. Kirkland v. United 

States, 558 U.S. 1116 (2010). 

Mr. Kirkland next moved to reduce his sentence based on the Fair Sentencing 

Act of 2010. The district court denied this motion. Order Mot. Reduce Sentence, 

United States v. Kirkland, No. 3:07-cr-30137-MJ-DGW, (S.D. Ill. Feb. 2, 2012). He 

sought the same relief—without success—twice more in the ensuing five years. See 

Mem. and Order, United States v. Kirkland, No. 3:07-cr-30137-MJ-DGW (S.D. Ill. 
3 

May 14, 2015); Min. Order, United States v. Kirkland, No. 3:07-cr-30137-MJ-DGW, 

(S.D. Ill. Feb. 2, 2012). Mr. Kirkland also moved for habeas relief under 28 U.S.C. 

§ 2255, asserting ineffective assistance of counsel before and during trial. Dismissal 

Order, Kirkland v. United States, No. 3:10-cv-00958-MJR, (S.D. Ill. Mar. 4, 2014). 

The court dismissed this motion. Id.

In March 2018, Mr. Kirkland—from federal prison in Kansas—applied for 

habeas relief under 28 U.S.C. § 2241. He argued the Supreme Court’s decisions in 

Descamps v. United States, 570 U.S. 254 (2013), and Mathis v. United States, 

136 S. Ct. 2243 (2016), provided a previously unavailable tool of statutory 

interpretation that undercut the sentencing court’s determination that his Missouri 

conviction was a predicate felony drug offense under 21 U.S.C. § 841. The district 

court dismissed this application because Mr. Kirkland failed to demonstrate that his 

§ 2255 remedy was inadequate under § 2255(e). 

About four months later, Mr. Kirkland filed a second § 2241 application in the 

District of Kansas, making the same arguments as he did in the first application. The 

district court dismissed for the same reason. Mem. and Order, Kirkland v. English, 

No. 5:18-cv-03186-JWL, (D. Kan. Aug. 3, 2018). Mr. Kirkland timely appealed this 

second dismissal. 

II. DISCUSSION 

A federal prisoner may pursue habeas relief under two statutes. The first is 

28 U.S.C. § 2241—the codification of the original federal habeas statute. See Hale 

v. Fox, 829 F.3d 1162, 1166 (10th Cir. 2016). “[A] prisoner must bring a § 2241 
4 

application in the district where he or she is incarcerated.” Id. Section 2241 does not 

limit the number of applications a prisoner may bring. See 28 U.S.C. § 2241; see 

also id. § 2244 (limiting habeas applications under § 2254 and § 2255). An 

application under 28 U.S.C. § 2241 generally attacks the execution of a sentence 

rather than its validity. Brace v. United States, 634 F.3d 1167, 1169 (10th Cir. 2011). 

 The second is 28 U.S.C. § 2255, which Congress enacted in 1948 “to distribute 

the work of collateral review more evenly among federal courts” by requiring 

prisoners to file in the court that convicted them. Hale, 829 F.3d at 1168. A prisoner 

may generally bring only one § 2255 motion, id. at 1165, but may bring a second 

motion with a certification from a circuit court that the motion contains: 

(1) newly discovered evidence that, if proven and viewed 

in light of the evidence as a whole, would be sufficient to 

establish by clear and convincing evidence that no 

reasonable factfinder would have found the movant guilty 

of the offense; or 

(2) a new rule of constitutional law, made retroactive to 

cases on collateral review by the Supreme Court, that was 

previously unavailable. 

28 U.S.C. § 2255(h). 

“A § 2255 motion is ordinarily the only means to challenge the validity of a 

federal conviction following the conclusion of direct appeal.” Hale, 829 F.3d at 

1165. But “in rare instances,” the “savings clause” in § 2255(e) permits a prisoner to 

avoid § 2255’s restriction on second and successive motions and bring an application 

under § 2241 instead. Id. (quotations omitted). The savings clause provides: 
5 

An application for a writ of habeas corpus [pursuant to 

§ 2241] in behalf of a prisoner who is authorized to apply for 

relief by motion pursuant to [§ 2255], shall not be entertained

if it appears that the applicant has failed to apply for relief, by 

motion, to the court which sentenced him, or that such court 

has denied him relief, unless it also appears that the remedy 

by motion [pursuant to § 2255] is inadequate or ineffective to 

test the legality of his detention.

28 U.S.C. § 2255(e) (emphasis added). “Thus, a federal prisoner may file a § 2241 

application challenging the validity of his sentence only if § 2255 is inadequate or 

ineffective to test the legality of his detention.” Hale, 829 F.3d at 1165 (quotations 

omitted). 

 A § 2241 applicant “bears the burden of showing he satisfies § 2255(e).” Id. at 

1170. “The relevant metric or measure” for application of § 2255(e) “is whether a 

petitioner’s argument challenging the legality of his detention could have been tested in 

an initial § 2255 motion.” Prost v. Anderson, 636 F.3d 578, 584 (10th Cir. 2011). If the 

argument could have been tested in an initial § 2255 motion, “then the petitioner may not 

resort to the savings clause and § 2241.” Id. We have identified only two examples in 

which § 2255 was inadequate or ineffective: (1) when the sentencing court has been 

abolished, or (2) “when the application of § 2255(h)’s bar against a second or 

successive motion for collateral review would seriously threaten to render the § 2255 

remedial process unconstitutional.” Hale, 829 F.3d at 1173-74 (quotations omitted). 

Mr. Kirkland does not contend his case meets either of the Prost exceptions. 

Instead, he urges us to apply a different savings clause gatekeeping rule—the 

erroneous-circuit-foreclosure test—recognized in Wooten v. Cauley, 677 F.3d 303, 
6 

307-08 (6th Cir. 2012), and In re Davenport, 147 F.3d 605, 611 (7th Cir. 1998). 

Under this test, the savings clause may be triggered if (1) circuit precedent at the time 

of the initial § 2255 motion precluded the applicant from arguing his conduct fell 

outside the scope of the statute of conviction, and (2) that precedent is later 

overturned, enabling the argument. See Lewis v. English, 736 F. App’x 749, 752 

(10th Cir. 2018). 

Mr. Kirkland argues that the Supreme Court announced in Descamps and 

Mathis a method of statutory interpretation that would render his prior Missouri 

conviction ineligible to enhance his federal sentence. He argues that because 

Descamps and Mathis had not been decided when he filed his § 2255 motion, they 

enable him to satisfy the savings clause. 

The district court correctly rejected this argument. Even if, under Descamps

and Mathis, his Missouri conviction were ineligible to enhance his federal sentence, 

Prost, which rejected the erroneous-circuit-foreclosure test, 636 F.3d at 590-93, 

precludes Mr. Kirkland’s savings clause argument. We turned down a similar 

argument in Prost—that a new case construing the statute he was convicted and 

sentenced under renders that conviction and sentence invalid. As with Mr. Prost, Mr. 

Kirkland cannot seek relief under § 2241 because he “was entirely free to raise and 

test a [Descamps-and-Mathis]-type argument in his initial § 2255 motion.” Prost, 

636 F.3d at 590. Accordingly, we need not evaluate Mr. Kirkland’s argument that his 

prior offense fails under Descamps and Mathis to qualify as a felony drug offense for 

the purposes of his sentence under 21 U.S.C. § 841. 
7 

III. CONCLUSION 

We affirm the district court’s dismissal of Mr. Kirkland’s § 2241 application. 

Entered for the Court 

Scott M. Matheson, Jr. 

Circuit Judge