Thomas Hurlow v. United States, 726 F.3d 958

Hurlow pled guilty to multiple drug and firearm offenses after drugs and a handgun were found at the home he shared with his fiancée.
He signed a plea agreement waiving his right to challenge conviction or sentence under 28 U.S.C. § 2255, and a stipulated factual basis stated Funk consented in writing to a search.
Hurlow claimed he advised trial counsel of facts suggesting Randolph v. Georgia violated, but counsel did not investigate and instead pressed for a guilty plea.
The district court found the § 2255 waiver barred the motion, and denied an evidentiary hearing; judgment entered September 26, 2011.
Hurlow attempted to appeal late; he argued the prison mailbox rule made his notice timely, which this court accepted after analysis of the prison mail system.
On remand, the court held that the collateral review waiver does not bar a challenge to the plea agreement based on ineffective assistance of counsel, and remanded for an evidentiary hearing on the Sixth Amendment claim.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Timeliness of Hurlow's appeal	Hurlow's notice was timely under the prison mailbox rule	F.C.I. Williamsburg lacked a legal mail system; no timely filing under Rule 4(c)	Timeliness established; prison mailbox rule applied
Enforceability of § 2255 waiver	Waiver does not bar claims that the plea was the product of ineffective assistance of counsel	Waiver generally bars collateral review; only permits challenges to waiver negotiation itself	Waiver does not bar claims that the plea was tainted by ineffective assistance of counsel
Scope of ineffective assistance overcoming waiver	Evidentiary showing that counsel’s performance rendered plea involuntary or tainted the agreement	General ineffective assistance claims are insufficient to defeat the waiver	Allegations show the plea was the product of ineffective assistance; remand for evidentiary hearing

Houston v. Lack, 487 U.S. 266 (U.S. 1988) (prison mailbox rule governs timely filing)
Craig, 368 F.3d 738 (7th Cir. 2004) (distinguishes legal mail systems from regular mail systems)
Ingram v. Jones, 507 F.3d 640 (7th Cir. 2007) (separate legal mail system required for Rule 4(c))
Jones v. United States, 167 F.3d 1142 (7th Cir. 1999) (waivers generally enforceable; ineffectiveness in negotiating waiver can carve exception)
Bridgeman v. United States, 229 F.3d 589 (7th Cir. 2000) (plea waiver enforceable unless involuntary or counsel ineffective in negotiating)
Hodges, 259 F.3d 655 (7th Cir. 2001) (appellate waiver not absolute barrier to ineffective assistance claims)
Jemison, 237 F.3d 911 (7th Cir. 2001) (ineffective assistance in plea negotiations can void waiver)
Cieslowski, 410 F.3d 353 (7th Cir. 2005) (plea-based collateral challenges may overcome waiver if plea tainted by counsel's ineffectiveness)
Tollet v. Henderson, 411 U.S. 258 (U.S. 1973) (claims of ineffective assistance may render plea involuntary; focus on advice and voluntariness)
Quintero, 618 F.3d 746 (7th Cir. 2010) (waiver stands or falls with the plea as a whole)
Teeter, 257 F.3d 14 (1st Cir. 2001) (illustrative on variability of miscarriage of justice in plea issues)
Behrman, 235 F.3d 1049 (7th Cir. 2000) (plea waiver may be challenged if plea itself was involuntary or the product of ineffectiveness)