OPINION & ORDER Defendant Steve Boria, proceeding pro se, moves under 28 U.S.C. §2255 to vacate, set aside, or correct his sentence, imposed after a guilty plea. Among Boria’s arguments for habeas relief is that his counsel failed to file the timely notice of appeal that he requested. Because this conduct constitutes ineffective assistance of counsel, Boria’s motion is granted in part and denied in part. The Court vacates its judgment and enters a new one with the same sentence, affording Boria the opportunity for direct appeal. BACKGROUND On December 27, 2018, Boria pled guilty to (1) conspiring to distribute and possess with the intent to distribute cocaine base, in violation of 21 U.S.C. §§841(b)(1)(B), 846; and (2) possessing and discharging a firearm in furtherance of that narcotics conspiracy, in violation of 18 U.S.C. §924(c)(1)(A)(iii). See Plea Tr. 7:5-8:22, 17:18, Dkt. No. 392. In connection with his guilty plea, Boria agreed that he would “not file a direct appeal; nor bring a collateral challenge, including but not limited to an application under Title 28, United States Code, Section 2255 and/or Section 2241.” Appendix at A34, United States v. Boria, No. 20-206 (2d Cir. Aug. 28, 2020). Notwithstanding this agreement, Boria reserved his right to appeal — whether directly or as a collateral challenge — based on ineffective assistance of counsel claims. See id. at A35. As the plea agreement further stated, Boria’s agreement not to file a direct appeal or bring a collateral challenge was not to “be construed to be a waiver of whatever rights [he] [might] have to assert claims of ineffective assistance of counsel, whether on direct appeal, collateral review, or otherwise. Rather, it is expressly agreed that [Boria] reserves those rights.” Id. On October 18, 2019, the Court imposed a fifteen-year term of imprisonment, to be followed by four years of supervised release. See J. 2-3, Dkt. No. 529. According to Boria, directly after his sentencing, he requested that his counsel at the time, Royce Russell, file a notice of appeal.1 See Mot. 5, Dkt. No. 596; Boria Aff. 2, Dkt. No. 702. Russell — through an affidavit ordered by the Court — acknowledges that he informed Boria that he would file a timely notice of appeal, despite Boria’s expressed intent to retain new counsel to file an appeal. See Russell Aff. 6. Russell, however, did not file a notice of appeal until January 13, 2020 — well beyond the fourteen-day requirement for doing so. See Notice Appeal, Dkt. No. 545; Fed. R. App. P. 4(b)(1)(A). Russell explains that he “inadvertently failed” to timely file the notice, but did so “immediately” once Boria’s family member communicated Boria’s outstanding request that he file the notice. Russell Aff.