MEMORANDUM AND ORDER
CARLOS MURGUIA United States District Judge
Defendant Nicholas Srader brings this Motion Under 28 U.S.C. § 2255 to Vacate, Set Aside, or Correct Sentence by a Person in Federal Custody (Doc. 123). Defendant argues he is being held in federal custody in violation of the Sixth Amendment of the United States Constitution and presents six grounds he believes establish his ineffective assistance of counsel claim.
I. Factual Background
Defendant was charged with being a felon in possession of a firearm on June 18, 2009, and was represented by several different attorneys over the next two years. On March 14, 2011, defendant pleaded guilty to the charge. At sentencing, defendant requested a downward departure, but the court denied the request. Because defendant had a previous violent crime conviction, the presentence investigation report calculated his base offense level to be 20. The court increased his level by two points with an obstruction of justice enhancement. Based on a total offense level of 22 and a criminal history category of V, defendant’s guideline sentencing range was 77 to 96 months imprisonment. The court sentenced him on December 6, 2011 to 96 months in prison.
Defendant argues that his attorneys—Kelly Kauffman (now Trussell), Robert Eye, Brett Jarmer and Scott Gyllenborg were constitutionally ineffective. Specifically: defendant contends that counsel (1) incorrectly advised him of the consequences of entering a guilty plea; (2) failed to effectively challenge the obstruction of justice enhancement; (3) failed to argue that defendant was entitled to an acceptance of responsibility credit; (4) failed to object to the final offense level; (5) failed to object to his criminal history calculation; and (6) failed to address defendant’s illegal detainment. The court examines each of these claims in turn.
II. Legal Standards
A. 28 U.S.C. § 2255
28 U.S.C. § 2255 gives federal prisoners the ability to file a motion to “vacate, set aside or correct a federal sentence.” To succeed, defendant must prove that “the sentence was imposed in violation of the Constitution or laws of the United States, or that the court was without jurisdiction to impose such a sentence, or that the sentence was without jurisdiction of the maximum authorized by law, or is otherwise subject to collateral attack.” 28 U.S.C. § 2255.
The court must hold an evidentiary hearing on a § 2255 motion “unless the motion and files and records of the case conclusively show that the prisoner is entitled to no relief.” Id.; United States v. Galloway, 56 F.3d 1239, 1240 (10th Cir. 1999). The defendant bears the burden to allege facts which, if proven, would entitle him to relief. See Hatch v. Oklahoma, 58 F.3d 1447, 1471 (10th Cir. 1995). “The allegations must be specific and particularized, not general or conclusory.” Id. at 1471.
B. Ineffective Assistance of Counsel
A defendant may bring an ineffective assistance of counsel claim in a collateral proceeding under 28 U.S.C. § 2255, regardless of whether he could have raised the claim on direct appeal. Massaro v. United States, 538 U.S. 500, 504 (2003). In analyzing an ineffective assistance of counsel claim, the court looks to the two-prong Strickland test established in Strickland v. Washington, 466 U.S. 668 (1982). The Strickland standard is “highly demanding.” Kimmelman v. Morrison, 477 U.S. 365, 382 (1986).
The first prong deals with deficient performance. For counsel’s performance to qualify as constitutionally ineffective, it must “fall below an objective standard of reasonableness.” Strickland, 466 U.S. at 687. “Performance must have been completely unreasonable, not merely wrong.” Barkell v. Crouse, 468 F.3d 684, 689 (10th Cir. 2006) (quoting Boyd v. Ward, 179 F.3d 904, 914 (10th Cir. 1999)) (applying the Strickland test). Review of counsel’s performance under the first prong of the Strickland test is highly deferential. “Counsel is strongly presumed to have rendered adequate assistance and made all significant decisions in the exercise of reasonable judgment.” Strickland, 466 U.S. at 690.
The second prong of the Strickland test requires counsel’s ineffective performance to prejudice the defendant. There must be “a reasonable probability that, but for counsel’s unprofessional errors, the result of the proceeding would have been different.” Id. at 694.
The court may consider either or both of the Strickland prongs: “There is no reason for a court deciding an ineffective assistance claim to approach the inquiry in any particular order or even to address both components of the inquiry if the ...