OPINION OF THE COURT
McKEE, Circuit Judge.
George Salerno brings this appeal after being sentenced for a crime commonly known as “cheek kiting.”1 Although he challenges his sentence on numerous grounds, we need only address his claim that he was denied his Sixth Amendment right to counsel at sentencing. Because we find this assertion to have merit we will remand for resen-tencing.
I.
On September 24, 1992, a federal grand jury returned a two-count indictment charging Salerno with bank fraud in violation of 18 U.S.C. § 1344. Prior to trial, the public defender who had been appointed to represent Salerno was allowed to withdraw, and the district court then appointed an attorney of Salerno’s own choosing to represent Salerno at trial. After a two day trial, the jury convicted Salerno of both counts.
Sentencing was originally set for January 10, 1994, however, on three separate occasions, Salerno moved pro se for a continuance of the sentencing date and the district court granted each request. On March 1, 1994, Salerno wrote to his trial attorney and asked him to withdraw as counsel. Salerno also wrote to the district court and requested new counsel and yet another postponement of the sentencing. He stated that given his request for a change of counsel, .he needed the continuance in order to have an opportunity to meet with an attorney and adequately prepare for sentencing. The sentencing hearing finally proceeded on April 4, 1994. At the [217]*217beginning of that hearing the following discussion occurred between the district judge, Salerno’s appointed counsel and Salerno:
THE COURT: We’re ready for the sentence of Mr. Salerno, but I understand that there are some preliminary matters which we need to deal with.
The first is Mr. Salerno may not wish to have you, [trial counsel]. I don’t know.
[TRIAL COUNSEL]: I’m perfectly aware of that, Your Honor. We have talked at length about it.
THE COURT: Do you wish to remain with him at counsel table or does he wish for you to step back and remain available as a standby counsel?
[TRIAL COUNSEL]: I will tell the Court what I told Mr. Salerno on several occasions. I will not withdraw voluntarily. If he does not want me seated here, I shall step back....
THE COURT: Mr. Salerno, do you wish to state anything in regard to [trial counsel]?
THE DEFENDANT: Yes, Your Honor. As far as the sentencing today, again, I’m going to reiterate my request that it be continued.
THE COURT: Well, first we have to determine — we’re not there yet. We’re going to deal with that.
THE DEFENDANT: All right. No, I had, as of March 1st, I wrote [my attorney] the letter that I’ve submitted to the Court, which I don’t know if you received it in the mail on Friday—
THE COURT: Yes.
THE DEFENDANT: —and I had asked him to withdraw. He came and saw me at Fairton and we spent about ten, fifteen minutes together and I was under the understanding that he was going to withdraw. I guess we had a misunderstanding that he was going to wait and see what the Court said....
We have not discussed the pre-sentence at all, I mean not in the slightest, and we haven’t discussed the sentencing problems at all. Therefore, if we went ahead with the sentencing, I would have to represent myself. [Trial counsel] is not prepared to do that based — and I filed an awful lot of material as the Court is aware on this — on any of the issues or any of the problems with the pre-sentence report_
I would prefer other representation.
THE COURT: Well, that’s why we continued the case the last time. This is not the first time you’ve been brought down for sentencing.
THE DEFENDANT: No, I understand that, Your Honor, very definitely.
THE COURT: And we thought that the reasons to continue the last sentencing were weak, but ... we thought we’d give you the benefit of the doubt and extend— continue the sentencing till today, but we’re not willing to continue it any further. So we’ll proceed.
THE DEFENDANT: Then I would have to represent myself, Your Honor....
I don’t know how he could represent me, not knowing any of the issues. You know, no slight to [trial counsel], but he doesn’t—
THE COURT: Well, we’ve looked at what you’ve submitted—
THE DEFENDANT: —but he doesn’t have a crystal ball, either.
THE COURT: —and there doesn’t seem to be much in issue.
Why don’t we go through what you want to raise and see if there’s anything in it that has any merit. On the surface, it doesn’t seem to have any merit; but maybe I’m missing something and we’ll give you an opportunity to explain.
Let’s take your points one by one and we’ll deal with them in that way.
What’s your first point?
THE DEFENDANT: May I sit, Your Honor?
THE COURT: Sure.
Why don’t you stay there in ease — he doesn’t bother you sitting there, right?
[TRIAL COUNSEL]: Better not. I’ve known him for too long.
THE DEFENDANT: No, no, not at ah. [My attorney] and I have known each other — we’re friends. We’ve known each other for 20 years.
THE COURT: Okay.
[218]*218THE DEFENDANT: That’s not a personal slight at all.
THE COURT: Okay. Okay.
App. at 525-28 (Transcript of Sentencing Hearing, April 4, 1994).
The district court then listened as Salerno argued the inaccuracy of the pre-sentence report and the application of case law to his situation. After rejecting Salerno’s arguments, the district court imposed a sentence of ninety-six months imprisonment, followed by five years supervised release, restitution of $15,000, no fine, and a $100 special assessment.
II.
When Salerno filed the notice of appeal from his sentence he requested appointment of counsel, and the district court appointed appellate counsel who filed a brief on Salerno’s behalf. Salerno has also filed a pro se brief in this appeal.2
Salerno raises an issue in his pro se brief that was not raised in the brief submitted by his attorney on appeal. Salerno claims that his purported waiver of counsel at the sentencing hearing was not knowing, intelligent and voluntary, and that the sentencing court therefore erred in allowing him to represent himself at sentencing. The government concedes that the trial court did not engage in an inquiry with Salerno to ascertain the extent of his understanding of the ramifications of dispensing with counsel and proceeding pro se at the sentencing hearing. Nevertheless, the government argues that “[t]he record that was before the trial court showed that Salerno understood the nature of the sentencing proceeding and the possible consequences.” Brief for Appellee at 34. The government further claims that the trial court properly inferred that Salerno’s waiver of counsel was knowing and intelligent and that the record supports that implicit finding.
A.
The Supreme Court has recognized that a criminal defendant has the constitutional right to defend him/herself at trial. Faretta v. California, 422 U.S. 806, 814-16, 95 S.Ct. 2525, 2530-31, 45 L.Ed.2d 562 (1975); Adams v. United States ex rel. McCann, 317 U.S. 269, 279, 63 S.Ct. 236, 241-42, 87 L.Ed. 268 (1942) (the Sixth Amendment right to counsel implicitly includes the “correlative right to dispense with a lawyer’s help”). The Court, however, has scrupulously required that a defendant’s waiver of counsel be both voluntary and a “knowing and intelligent relinquishment or abandonment of a known right or privilege.” Edwards v. Arizona, 451 U.S. 477, 482, 101 S.Ct. 1880, 1883-84, 68 L.Ed.2d 378 (1981). Whether a defendant has voluntarily, knowingly and intelligently relinquished the right to counsel “depends in each case ‘upon the particular facts and circumstances surrounding that case, including the background, experience, and conduct of the accused.’ ” Id. (quoting Johnson v. Zerbst, 304 U.S. 458, 464, 58 S.Ct. 1019, 1023, 82 L.Ed. 1461 (1938)). In general, however, the Supreme Court has required that “courts indulge in every reasonable presumption against waiver.” Brewer v. Williams, 430 U.S. 387, 404, 97 S.Ct. 1232, 1242, 51 L.Ed.2d 424 (1977).
In United States v. Welty, 674 F.2d 185 (3d Cir.1982), we set forth guidelines for conducting a proper inquiry following a defendant’s request for substitution or waiver of counsel:
First, the court must decide if the reasons for the defendant’s request for substitute counsel constitute good cause and are thus sufficiently substantial to justify a continuance of the trial in order to allow new counsel to be obtained. If the district court determines that the defendant is not entitled to a continuance in order to engage new counsel, the defendant is then left with a choice between continuing with his existing counsel or proceeding to trial pro se, thus bringing into play the court’s [219]*219second stage of inquiry. Since the decision to proceed pro se involves a waiver of the defendant’s sixth amendment right to counsel, the district court then has the responsibility of ensuring that any decision by the defendant to represent him[/her]self is intelligently and competently made.
It is vital that the district court take particular pains in discharging its responsibility to conduct these inquiries concerning substitution of counsel and waiver of counsel.... [A] trial cannot be permitted to go forward when a defendant does not fully appreciate the impact of his[/her] actions on his|7her] fundamental constitutional rights.
Id. at 187 (citation omitted).
In Welty, we concluded that the defendant could not have effectively waived his right to counsel because “the record reveal[ed] no inquiry by the district court judge as to the reasons for Welty’s dissatisfaction with his appointed counsel and little inquiry into whether Welty’s decision to proceed pro se was made knowingly and intelligently.” Id. at 189. Similarly, in McMahon v. Fulcomer, 821 F.2d 934 (3d Cir.1987), we held that the defendant did not knowingly and intelligently waive his right to counsel where the “record reflected] a total absence of any ‘searching inquiry’ or colloquy as to defendant’s understanding of the dangers and disadvantages he faced proceeding pro se.” Id. at 945.
Conversely, we upheld the validity of a defendant’s waiver of counsel in Government of Virgin Islands v. James, 934 F.2d 468 (3d Cir.1991). There, the trial court was not presented with a request for substitute counsel as James sought only to represent himself. Throughout the pre-trial proceedings James had been represented by a public defender. However, when jury selection was to begin James told the court that he wanted to discharge his attorney and represent himself. Id. at 470. The district judge conducted a lengthy colloquy with James in which the court informed him of the perils of self-representation. Id. at 470. On review, we considered the contents of that colloquy and concluded that James’ waiver was knowing and intelligent:
After admonishing appellant with the old adage that a lawyer who has himself for a client is a fool, the court discussed the nature of the possible charges against James and the possible penalties he faced; James was apprised of the difficulty he would face in getting his decision to waive overturned on appeal from a conviction; the court determined that James had some familiarity with the workings of a trial as a result of two prior convictions; the court also determined that James’ waiver was voluntary.... Most significantly, the court did not allow James to proceed completely unassisted but appointed stand-by counsel to sit with him and answer any questions that he may have had during trial.
Id. at 472-73.3
B.
The issue before us is, of course, raised in a different context as Salerno’s purported waiver occurred at sentencing as opposed to trial. This distinction is clearly relevant to the content of the colloquy which the court must have with the defendant. It does not, however, eliminate the need for the district court to make an inquiry sufficient to support a finding that the waiver of counsel is voluntary, knowing and intelligent.
It is well settled that “[i]t is the solemn duty of a federal judge before whom a defendant appears without counsel to make a thorough inquiry and to take all steps necessary to insure the fullest protection of this constitutional right at every stage of the proceedings.” Von Moltke v. Gillies, 332 U.S. 708, 722, 68 S.Ct. 316, 322, 92 L.Ed. 309 (1948) (Black, J., plurality opinion) (emphasis added). Neither logic nor precedent supports carving out an exception when the waiver occurs at sentencing. Of course, the inquiry at sentencing need only be tailored to that proceeding and the consequences that may flow from it. Therefore, it need not be as exhaustive and searching as a similar inquiry before the conclusion of trial. “Sen[220]*220tencing hearings demand much less specialized knowledge than trials; for instance, the Federal Rules of Evidence do not apply in sentencing hearings.” United States v. Day, 998 F.2d 622, 626 (1st Cir.1993), cert. denied, — U.S. —, 114 S.Ct. 2140, 128 L.Ed.2d 868 (1994). Nevertheless, sentencing is a critical and often times complicated part of the criminal process that contains subtleties which may be beyond the appreciation of the average layperson seeking to represent him/herself.
We have, for example, previously noted that “[t]he [Sentencing] Guidelines contain a complex procedure for determining the appropriate increase in offense level for conviction of multiple counts.” United States v. Johnson, 931 F.2d 238, 242 (3d Cir.1991). See also United States v. Smith, 997 F.2d 396, 398 (8th Cir.1993) (Gibson, J., concurring) (“The guidelines ... have created a complex hypertechnical system consuming great amounts of judicial time for both trial and appellate judges.”). Commentators have also bemoaned the complexities of our sentencing system. Id. at 399 (Bright, J., dissenting) (citing articles that “call attention to the frustrations of lawyers, judges and probation officers who must try to understand the complexities of the [sentencing] system”).
Indeed, in some cases, one’s ultimate fate is determined more by the application of the Guidelines than the determination of innocence or guilt. For example, sentencing judges are not limited to a consideration of the specific conduct that constitutes the offense of conviction in determining whether a given offense characteristic applies. Under USSG § 1B1.3, a judge generally must consider all “relevant conduct.”4 Thus, “[t]he Guidelines are clear that conduct beyond the precise acts of the offense of conviction may be used to determine specific offense characteristics.” United States v. Frierson, 945 F.2d 650, 653 (3d Cir.1991). Accordingly, we have upheld sentences which were based in part upon conduct for which the defendant was not convicted. See United States v. Cianscewski, 894 F.2d 74, 80-81 (3d Cir.1990); United States v. Ryan, 866 F.2d 604, 608-09 (3d Cir.1989). Given these intricacies, it is particularly important that a sentencing court be certain that a defendant understands the perilous path he/she is going down in attempting to proceed to sentencing without the benefit of counsel.
In addition, a defendant who is unfamiliar with the post conviction process may inadvertently waive a meritorious argument that he/she might otherwise have raised on appeal. Thus, at sentencing, just as at trial, “a defendant’s waiver of counsel can be deemed effective only where the district court has made a searching inquiry sufficient to satisfy him[/her] that the defendant’s waiver was understanding and voluntary.” Welty, 674 F.2d at 189. We have not previously, nor do we now, require a rote dialogue “such as that mandated for guilty plea proceedings conducted pursuant to Rule 11 of the Federal Rules of Criminal Procedure.” James, 934 F.2d at 473. However, at a minimum, a trial judge must make “a searching inquiry sufficient to satisfy himlTher] that the defendant’s waiver was understanding and voluntary.” Welty, 674 F.2d at 189. The court’s inquiry-must be calculated to insure that the defendant is “made aware of the dangers and disadvantages of self-representation, so that the record will establish that ‘he[/she] knows what he|7she] is doing and [the] choice is made with eyes open.’ ” Faretta, 422 U.S. at 834, 95 S.Ct. at 2541 (quoting Adams, 317 U.S. at 279, 63 S.Ct. at 242). “Perfunctory questioning is not sufficient.” Welty, 674 F.2d at 187. Where the record contains no such inquiry, or one that is inadequate, there can be no valid waiver of the right to counsel. [221]*221Salerno’s purported waiver was accepted without such an inquiry and therefore it cannot stand.
C.
The inquiry required here did not have to include a discussion of the reasons for Salerno’s request for a continuance in order to get new counsel because Salerno clearly stated the reasons for his dissatisfaction when he requested another continuance of the sentencing date. See McKee v. Harris, 649 F.2d 927, 938 (2d Cir.1981). When a defendant insists on proceeding pro se, the next inquiry a court must make under Welly is whether the defendant’s request for waiver of counsel is voluntary, knowing and intelligent. Here, Salerno’s own language casts doubt upon the voluntariness of his request. Although a defendant can be deemed to have waived the right to counsel by refusing the assistance of appointed counsel and persisting in a demand for different counsel, see Wiggins v. Procunier, 753 F.2d 1318, 1320 (5th Cir.1985), a defendant will not normally be deemed to have waived the right to counsel by reluctantly agreeing to proceed pro se under circumstances where it may appear that there is no choice. See United States ex rel. Martinez v. Thomas, 526 F.2d 750, 755-56 (2d Cir.1975) (defendant who represented himself “reluctantly, unwillingly and greatly to his detriment” had “no freedom of choice” but was merely “bowing to the inevitable,” and was thereby denied his constitutional rights). Here, the circumstances were such that the district court had an obligation to make a sufficient inquiry of the defendant to allow the court to decide whether the defendant was “bowing to the inevitable” or voluntarily and affirmatively waiving his right to counsel.
We do not, however, suggest that the district court should have allowed itself to be manipulated into granting a continuance and appointing new counsel. Nevertheless, the defendant’s apparent reluctance to proceed without counsel should have alerted the court to the need to inform the defendant of the pitfalls and technicalities of the sentencing hearing which was about to begin. Such a warning would have better enabled the defendant to decide if he still wanted to proceed pro se instead of allowing counsel, who was standing at his side, to represent him.
We appreciate that the sentencing judge (who also conducted Salerno’s trial) may have felt that he had sufficient familiarity with this defendant to accept a waiver of counsel for purposes of sentencing without a searching inquiry into Salerno’s familiarity with, or appreciation of, the complexities of sentencing. Before sentencing, Salerno, acting pro se, filed several documents including an extensive challenge to the pre-sentence report, objections to the revised pre-sentence report, a sentencing memorandum, a letter tó the trial court objecting to the government’s sentencing memorandum, and voluminous exhibits in support of his arguments.5 Thus, we can understand how the sentencing judge may have concluded that Salerno was better able to represent himself than the average defendant. However, we cannot infer a valid waiver of the right to counsel based upon the district court’s subjective overall impression of a defendant. We have previously stated “that a colloquy between the defendant and trial judge is the preferred method of ascertaining that a waiver is voluntary, knowing and intelligent.” James, 934 F.2d at 473. See also Wiggins, 753 F.2d at 1320 (“We are convinced that a colloquy between a defendant and a trial judge is the preferred method of ascertaining that a waiver is voluntary, knowing and intelligent.”). We reiterate that “[i]t is appropriate for this searching inquiry to appear upon the record,” McMahon, 821 F.2d at 945, so as to allow a reviewing court to examine the district court’s determination in the event of an appeal. Here, the district court’s failure to do this requires a remand for resentencing.
Moreover, we decline to engage in a harmless error analysis here. The right to representation by counsel in a criminal [222]*222proceeding is one of the most fundamental and cherished rights guaranteed by the Constitution. See Johnson, 304 U.S. at 462, 58 S.Ct. at 1022 (describing assistance of counsel as “one of the safeguards of the Sixth Amendment deemed necessary to insure fundamental human rights of life and liberty”). It is “among those ‘constitutional rights [which are] so basic to a fair trial that their infraction can never be treated as harmless error.’ ” Welty, 674 F.2d at 194 n. 6 (quoting Chapman v. California, 386 U.S. 18, 23 & n. 8, 87 S.Ct. 824, 827 & n. 8, 17 L.Ed.2d 705 (1967)). Furthermore, the purpose and effect of the Sixth Amendment is to “withhold[] from federal courts, in all criminal proceedings, the power and authority to deprive an accused of his life or liberty unless he has or waives the assistance of counsel.” Johnson, 304 U.S. at 463, 58 S.Ct. at 1022 (footnotes omitted). . Accordingly, we do not feel that the deprivation of the defendant’s right to representation at sentencing under the circumstances of this case justifies a harmless error analysis.
In summary, we do not believe that the district court’s instruction for Salerno’s appointed counsel to serve as standby counsel during the sentencing is a sufficient substitute for obtaining a valid waiver of the right to counsel from the defendant. Although the court’s instruction was a noteworthy attempt to safeguard Salerno’s Sixth Amendment right, it did not satisfy the court’s “responsibility of ensuring that any choice of self-representation is made ... with an awareness of the dangers and disadvantages inherent in representing oneself.” Welty, 674 F.2d at 188.
III.
Salerno raises several other issues pertaining to his sentencing. He claims that the district court improperly calculated the amount of loss by “double counting” the same funds as both actual and intended loss. He argues that his sentence level should be reduced by three points because his federal conviction in Florida and state conviction in Arizona were part of a common scheme as defined in USSG § 4A1.2. Further, Salerno objects to the two point enhancement he received for “more than minimal planning” and complains that he was improperly denied a two point reduction for acceptance of responsibility. Lastly, Salerno, through the brief submitted by his counsel, complains that he did not receive “sufficient notice” of the potential for sentence enhancement for commission of a crime while on bail release, as required by the Background Commentary accompanying USSG § 2J1.7. We decline to take any position as to the merits of any of these arguments now. On remand, these arguments can be presented to the sentencing court by competent legal counsel, or by the defendant after an appropriate waiver of counsel.
We will affirm the judgment of conviction but will vacate the sentence and remand for resentencing.