No COA Without Confronting the Procedural Ruling: Tenth Circuit Reaffirms Exhaustion and Issue Preservation in § 2241 Parole-Eligibility Challenges

Introduction

In Medina v. Bauby, No. 24-1495 (10th Cir. Apr. 1, 2025), the United States Court of Appeals for the Tenth Circuit denied state prisoner Delano Medina’s application for a certificate of appealability (COA) and his motion to proceed in forma pauperis (IFP), dismissing his appeal as frivolous. The case arises from a habeas petition under 28 U.S.C. § 2241 in which Mr. Medina challenged the Colorado Department of Corrections’ calculation of his sentences for purposes of parole eligibility.

The district court dismissed Mr. Medina’s § 2241 petition without prejudice for failure to exhaust state remedies. On appeal, Mr. Medina attempted to shift the debate to questions not raised in the district court—namely, whether his claim could be brought under 42 U.S.C. § 1983 and whether a different habeas proceeding should have been reopened under Federal Rule of Civil Procedure 60(b). The Tenth Circuit refused to entertain those new issues, held that Mr. Medina failed to challenge the actual ground for dismissal (non-exhaustion), and concluded he had not met the dual requirements for a COA following a procedural dismissal.

Although issued as a nonprecedential order, the decision powerfully restates two bedrock habeas principles in the Tenth Circuit: (1) state prisoners using § 2241 to challenge the execution of their sentences—including parole eligibility calculations—must exhaust state remedies by giving the state courts one complete round of review; and (2) to obtain a COA after a procedural dismissal, an appellant must directly confront and show the debatability of the procedural ruling itself. The opinion also underscores ordinary rules of issue preservation on appeal and clarifies the IFP standard when the appeal advances only nonresponsive arguments.

Summary of the Opinion

The Tenth Circuit panel (Judges Matheson, Phillips, and McHugh) denied Mr. Medina’s COA and IFP motion and dismissed the appeal as frivolous. The court held:

Mr. Medina’s § 2241 petition, which challenged sentence calculation for parole eligibility, was properly dismissed without prejudice by the district court due to non-exhaustion of state remedies. He was actively litigating the constitutional theory underlying his petition in a still-pending state postconviction proceeding, and his earlier state filings did not fairly present the same claim.
On appeal, Mr. Medina did not address the district court’s procedural ground for dismissal (non-exhaustion). Under Slack v. McDaniel, when a habeas petition is dismissed on a procedural ground, a COA requires a showing that reasonable jurists could debate both the validity of the constitutional claim and the correctness of the procedural ruling. Mr. Medina’s failure to challenge the procedural ruling was fatal to his COA request.
The two issues he did brief—whether § 1983 was the proper vehicle and whether a different habeas matter should have been reopened under Rule 60(b)—were not raised in this district court action and therefore were not properly before the appellate court. The panel noted it had already rejected those same arguments in his earlier appeals (Medina v. Murphy and Medina v. Caley).
Because Mr. Medina failed to present a reasoned, nonfrivolous argument supporting the issues actually before the court, his IFP motion also failed under DeBardeleben v. Quinlan.

Analysis

Precedents Cited and Their Influence

O’Sullivan v. Boerckel, 526 U.S. 838 (1999): The Supreme Court’s exhaustion doctrine requires a state prisoner to give the state courts “one complete round” of the established appellate process before pursuing federal habeas relief. The panel relied on O’Sullivan to affirm that simultaneous state postconviction litigation on the same claim defeats exhaustion.
Montez v. McKinna, 208 F.3d 862 (10th Cir. 2000): The Tenth Circuit reads § 2253(c)(1)(A)’s COA requirement to apply to state prisoners proceeding under § 2241 when the detention flows from a state court order. The panel cited Montez to confirm Mr. Medina needed a COA to appeal the dismissal of his § 2241 petition.
Miller-El v. Cockrell, 537 U.S. 322 (2003), and United States v. Silva, 430 F.3d 1096 (10th Cir. 2005): Together establish the COA threshold—whether reasonable jurists could debate the district court’s resolution or the issues deserve encouragement to proceed. These cases set the general COA framework.
Slack v. McDaniel, 529 U.S. 473 (2000): When a habeas petition is denied on a procedural ground, the applicant must show it is debatable both that the petition states a valid constitutional claim and that the procedural ruling was correct. Slack supplied the dispositive test here; Mr. Medina failed the procedural prong by not addressing exhaustion at all.
Preiser v. Rodriguez, 411 U.S. 475 (1973): Establishes that when a prisoner seeks immediate or speedier release, habeas is the exclusive federal remedy—not § 1983. The panel referenced Preiser via its earlier decision in Medina v. Murphy to show it had already rejected Mr. Medina’s § 1983 theory in a separate suit.
DeBardeleben v. Quinlan, 937 F.2d 502 (10th Cir. 1991): To proceed IFP on appeal, an applicant must show both indigency and a reasoned, nonfrivolous argument on law and facts. Mr. Medina failed to present any nonfrivolous argument addressing the operative ground for dismissal.
James v. Wadas, 724 F.3d 1312 (10th Cir. 2013): Courts liberally construe pro se filings but do not act as an advocate. The panel acknowledged Mr. Medina’s pro se status yet enforced preservation and COA standards.

Legal Reasoning

The opinion proceeds in three logical steps: jurisdiction (COA), the merits of the COA request under Slack, and IFP.

First, jurisdictionally, a state prisoner appealing the dismissal of a § 2241 petition must obtain a COA. Citing Montez, the court confirmed that § 2253(c)(1)(A) applies to § 2241 petitions related to state-court detention. Without a COA, the appellate court cannot reach the merits.

Second, on the COA standard, the district court had dismissed Mr. Medina’s petition without prejudice on a procedural ground—failure to exhaust state remedies. Under Slack, Mr. Medina therefore had to show it was debatable among reasonable jurists both that (1) his petition states a valid constitutional claim and (2) the district court’s procedural ruling was incorrect. The panel emphasized that the “only relevant issue” in this appeal was whether the district court correctly deemed the § 2241 claim unexhausted.

Mr. Medina did not engage with that issue. Instead, he argued two points unrelated to this case’s dismissal: that his claim could be brought under § 1983 and that a different habeas case should have been reopened. The panel refused to consider those arguments for two independent reasons:

They were not raised in the district court in this action and thus were not preserved for appellate review.
The Tenth Circuit had already rejected them in his recent, separate appeals (Medina v. Murphy on the § 1983 question; Medina v. Caley on the Rule 60(b) motion to reopen a different § 2241 petition).

With no argument directed at the actual procedural ruling (non-exhaustion), Mr. Medina could not satisfy Slack’s procedural prong. That ended the COA inquiry. The court did not need to consider the underlying constitutional merits or the nuances of whether his present claim matched those raised in prior state proceedings—because his COA application never contested the district court’s exhaustion rationale.

Third, on IFP, the court applied DeBardeleben’s two-part test. Even assuming indigency, an IFP applicant must show a reasoned, nonfrivolous appellate argument. Mr. Medina offered none responsive to the dispositive issue. Because the appeal did not present a colorable challenge to the exhaustion ruling, the court denied IFP and dismissed the appeal as frivolous.

Impact

While labeled nonprecedential, the order carries practical and persuasive force for prisoners, counsel, and district courts across the Tenth Circuit:

Exhaustion in § 2241 parole-eligibility challenges: The decision fortifies the requirement that state prisoners challenging the calculation or execution of their sentences (such as time credits or parole eligibility) must exhaust state judicial remedies before seeking federal § 2241 relief. Active, ongoing state postconviction litigation on the same claim generally defeats exhaustion and warrants dismissal without prejudice.
Precision at the COA stage after procedural dismissals: The opinion is a clear reminder that COA applications must directly confront and show the debatability of the procedural ruling that caused dismissal. Ignoring the procedural ground and rearguing other points—especially those previously rejected in separate matters—will foreclose a COA under Slack.
Issue preservation remains essential, even for pro se litigants: The court’s insistence on addressing only issues raised below reinforces the expectation that habeas appellants must preserve and brief the controlling issues. Liberal construction does not permit the court to recast an appellant’s arguments.
IFP is not a back door: The court reiterates that IFP status requires more than indigency; it requires a nonfrivolous legal theory tied to the actual appellate issues. Appeals that do not engage the district court’s stated grounds risk denial of IFP and dismissal as frivolous.
Pathway forward is preserved: Because the dismissal was without prejudice, petitioners in Mr. Medina’s position may return to federal court after fully exhausting state remedies, provided they fairly present the same federal constitutional claim through one complete round of the state’s appellate review.

Complex Concepts Simplified

Section 2241 vs. Section 2254: Both are federal habeas statutes. Section 2254 typically governs challenges to the validity of a state conviction or sentence; § 2241 is often used for challenges to the execution of a sentence (e.g., good-time credits, parole eligibility calculations). State prisoners proceeding under § 2241 still must exhaust state remedies, and in the Tenth Circuit, still must obtain a COA to appeal.
Exhaustion and “one complete round”: Before filing federal habeas, a state prisoner must present the same federal constitutional claim to the state courts and allow the established appellate process to run its course (e.g., trial court, intermediate appellate court, and, if part of the ordinary process, the state’s court of last resort). Claims still being litigated in state court are unexhausted.
Fair presentation: It’s not enough to raise vaguely similar issues in state court. The petitioner must fairly present the same legal theory and operative facts later advanced in federal court, and must frame the claim as a federal constitutional issue.
Certificate of Appealability (COA): A jurisdictional gatekeeping device for habeas appeals. To obtain a COA, the applicant must show that reasonable jurists could debate the district court’s ruling or that the issues are adequate to deserve encouragement to proceed further. When the district court’s decision rests on a procedural ground, Slack requires the applicant to show debatability as to both the underlying constitutional claim and the procedural ruling.
Issue preservation and raising new issues on appeal: Appellate courts generally do not consider issues not raised in the district court. Arguments must be preserved below and then properly presented in the opening brief. Repackaging a dispute from another case or raising it for the first time on appeal is typically ineffective.
In forma pauperis (IFP): Allows an indigent litigant to proceed without paying filing fees. But IFP also requires a nonfrivolous argument on the law and facts relevant to the appeal. An appeal that fails to address the dispositive ruling is often deemed frivolous.
Dismissal without prejudice: The case is closed, but the petitioner can refile later. In the habeas context, dismissals for non-exhaustion are commonly without prejudice, preserving the ability to return after completing state-court review.

Conclusion

Medina v. Bauby offers a concise yet instructive application of core habeas doctrines in the Tenth Circuit. Its central messages are straightforward:

For § 2241 challenges to parole-eligibility or other execution-of-sentence issues, exhaustion remains mandatory. Pending state postconviction proceedings on the same claim typically mean the federal petition is premature.
A COA following a procedural dismissal requires focused engagement with the procedural ruling. Under Slack, ignoring the procedural basis for dismissal dooms the application.
Appeals must be confined to issues preserved below; attempts to relitigate issues from other cases or to inject new issues will not be entertained.
IFP demands a reasoned, nonfrivolous appellate argument tied to the actual questions presented.

Although nonprecedential, the opinion reinforces well-settled principles with direct practical implications. Petitioners should complete state review and craft COA applications that cogently contest any procedural grounds for dismissal; failure to do so, as Medina’s case demonstrates, will result in denial of a COA, denial of IFP, and dismissal of the appeal.