§ 2255 Motions & Federal Post-Conviction Relief

The direct appeal is decided, and it is affirmed. Most people are told at that point that the case is over. It is not quite, but the remaining window is narrow and it closes on a schedule.

A § 2255 motion is a different proceeding with a different purpose. An appeal argues that the record shows an error. A § 2255 motion argues something the record does not show — usually that your own lawyer failed you.

What § 2255 is, and what it is not

28 U.S.C. § 2255 lets a prisoner in federal custody move the sentencing court to vacate, set aside, or correct a sentence. It is not a second appeal, and courts are firm about the distinction: issues already decided on direct appeal cannot be re-litigated, and issues that could have been raised on appeal but were not are generally defaulted.

The grounds are that the sentence was imposed in violation of the Constitution or federal law, that the court lacked jurisdiction, that the sentence exceeded the maximum authorized, or that it is otherwise subject to collateral attack.

The one-year deadline, and when it actually starts

Section 2255(f) gives one year, running from the latest of four dates:

• The date the judgment of conviction became final — which, if you sought certiorari, is when the Supreme Court denied it, and if you did not, is when the time to do so expired;
• The date a government-created impediment to filing was removed;
• The date the Supreme Court recognized a new right, if that right has been made retroactively applicable to collateral cases;
• The date on which the facts supporting the claim could have been discovered through due diligence.

The fourth trigger matters in ineffective assistance cases, where the defendant may not learn what counsel failed to do until well after the appeal. Equitable tolling exists but is narrow — it requires diligent pursuit of rights plus an extraordinary circumstance that prevented timely filing. Being unaware of the deadline is not one.

The main event: ineffective assistance of counsel

Most § 2255 motions allege that trial or appellate counsel was constitutionally ineffective. The standard comes from Strickland v. Washington, 466 U.S. 668 (1984), and has two prongs, both of which must be satisfied:

Deficient performance. Counsel's representation fell below an objective standard of reasonableness. Courts apply a strong presumption that challenged actions were sound strategy, so the claim has to identify something outside the range of reasonable professional judgment — not merely a decision that turned out badly.

Prejudice. There is a reasonable probability that, but for the deficiency, the result would have been different. In the plea context, Hill v. Lockhart frames this as whether the defendant would have insisted on going to trial; where counsel failed to convey or properly advise on a plea offer, Missouri v. Frye and Lafler v. Cooper supply the framework.

Claims that recur and succeed: failing to investigate an obvious defense, failing to file a plainly meritorious suppression motion, giving materially wrong advice about sentencing exposure or immigration consequences, failing to convey a plea offer, and failing to file a requested notice of appeal — the last of which carries a presumption of prejudice under Roe v. Flores-Ortega.

Procedural default, and the IAC exception

A claim not raised on direct appeal is generally defaulted unless you show cause and actual prejudice, or actual innocence. This trips up a great many pro se filings.

There is an important exception. In Massaro v. United States, 538 U.S. 500 (2003), the Supreme Court held that an ineffective assistance claim is not defaulted by failure to raise it on direct appeal — precisely because such claims usually depend on facts outside the trial record. Section 2255 is the intended forum for them.

Collateral-attack waivers in plea agreements

Most federal plea agreements contain a waiver of the right to appeal and to bring a collateral attack. These are generally enforceable if knowing and voluntary — but they are not absolute.

Courts commonly decline to enforce them against a claim that counsel was ineffective in negotiating the plea or the waiver itself, on the reasoning that a waiver cannot insulate the very advice that produced it. Waivers also do not bar claims that the sentence exceeded the statutory maximum. Whether a specific waiver forecloses a specific claim is a question worth analysing carefully rather than assuming.

How the motion actually proceeds

The motion is filed in the sentencing court, before the judge who imposed the sentence. The court may dismiss it without a hearing if the record conclusively shows no entitlement to relief, which is what happens to most of them. An evidentiary hearing — where trial counsel typically testifies and the attorney-client privilege is treated as waived on the relevant issues — is granted where the claim turns on contested facts outside the record.

There is no constitutional right to appointed counsel in a § 2255 proceeding, though the court may appoint counsel and generally must if a hearing is held.

Certificates of appealability and second motions

If the motion is denied, appealing requires a certificate of appealability under 28 U.S.C. § 2253(c) — a showing that reasonable jurists could debate whether the motion should have been resolved differently. Without one, the Fifth Circuit will not hear it.

A second or successive § 2255 motion requires authorisation from the court of appeals under § 2255(h), available only for newly discovered evidence establishing innocence by clear and convincing evidence, or a new rule of constitutional law made retroactive by the Supreme Court. Permission is rarely given. Treat the first motion as the only one — and raise every available claim in it, because omitted claims are usually gone for good.