source: Caselaw Access Project

author: BARBADORO, District Judge. KAYATTA, Circuit Judge,

license: Public Domain

text:
    UNITED STATES of America, Appellee, v. Christopher HENRY, Defendant, Appellant.
    No. 15-2487
    United States Court of Appeals, First Circuit.
    January 18, 2017

      Christine DeMaso, Assistant Federal Public Defender, with whom the Federal Defender Office was on brief, for Appellant.
    Vijay Shanker, Attorney, United States Department of Justice, Criminal Division, Appellate Section, with whom Leslie R. Caldwell, Assistant Attorney General, Sung-Hee Suh, Deputy Assistant Attorney General, Carmen M. Ortiz, United States Attorney, Glenn A. Mackinlay, Assistant United States Attorney, and John Albert Wortmann,. Jr., Assistant United States Attorney, were on brief, for Appellee.
    Before THOMPSON and KAYATTA, Circuit Judges, and BARBADORO, District Judge.

       Of the District of New Hampshire, sitting by designation.

   BARBADORO, District Judge.

Christopher Henry was convicted after a trial of possession of crack cocaine with intent to distribute. He claims on appeal that the district court erroneously failed to suppress text messages the police obtained from his cell phone pursuant to a search warrant. He also faults the district court for admitting evidence of his prior drug conviction, allowing a police officer to provide inadmissible expert testimony, and failing to instruct' the jury on the lesser included offense of simple possession. We affirm.

I. BACKGROUND

A. The Crimes

May 29, 2014, was the three-year anniversary of the death of a Boston-area gang member, and the police were informed that his family would be holding a memorial gathering at their home that night. Concerned that the event might spark violence, two police officers were dispatched to patrol the neighborhood in a car that was unmarked but that could be identified as a police vehicle based on its make, model, and accessories. As the officers drove toward the address where the gathering was expected, they saw two men standing on the sidewalk. When they drove past, one of the men, later identified as Henry, appeared shocked. Suspicious, the officers stopped and reversed toward the men. Upon seeing the car reverse, Henry and the other man took off running.

The officers gave chase, one by foot and one by car. Henry momentarily eluded the officer on foot by jumping over a fence and running through a schoolyard marked with “no trespassing” signs. The officer then glimpsed Henry running into the yard of a nearby home. He followed Henry into the yard and saw him facing another fence, topped with barbed wire. The officer identified himself, ordered Henry to the ground, frisked him, and arrested him for trespassing. A gun was subsequently found in the driveway of the home on the other side of the fence from where Henry was arrested.

The second man, later identified as Dwayne Leaston-Brown, ran around the side of the school building and disappeared from view. He was eventually found sitting on the steps of the same home where the gun was found. A second gun, bearing Leaston-Brown’s fingerprints, was discovered next to the school building along the path he followed as he fled from the police.

Henry was taken to the police station following his arrest where he was booked and thoroughly searched. A search of his pants produced a cell phone and $830 in cash, denominated mostly in $20 bills. Underneath his pants, Henry was wearing a pair of basketball shorts. A search of the shorts produced 21 individually packaged rocks of crack cocaine and two loose rocks, amounting to approximately three grams.

The police later applied for and received a warrant to search Henry’s cell phone. The search yielded coded text messages that appeared to reference drug sales. Henry was ultimately indicted for possession of crack cocaine with intent to distribute based on the cocaine the police found during the search at the police station, and possession of a firearm by a convicted felon based on the gun the police discovered in the driveway of the home across the fence from where he was arrested.

B. Proceedings Below

Henry moved to suppress the text messages obtained from the cell phone search on the ground that the search warrant application failed to establish probable cause. In rejecting Henry’s motion, the district court relied on the quantity and packaging of the drugs and the large amount of cash Henry was carrying, the discovery of the gun nearby, and the fact that Henry was carrying the cell phone at the time of his arrest. The court also gave weight to the affiant’s training and experience, which led him to conclude that cell phones are critical tools of the modern drug trade. Alternatively, the court determined that the text messages should not be suppressed even if the search was not supported by probable cause because the police relied in good faith on the search warrant when they conducted the search.

The government filed a motion in limine prior to trial asking the court to admit evidence of Henry’s 2012 state court conviction for possession of crack cocaine with intent to distribute. Henry challenged the government’s motion by arguing that evidence of his past criminal conduct was inadmissible propensity evidence that should be excluded under Rules 404(b) and 403 of the Federal Rules of Evidence. In rejecting Henry’s arguments, the district court concluded that Henry’s prior criminal conduct was admissible under Rule 404(b) to prove intent and modus operandi. The court also refused to exclude the prior conviction evidence pursuant to Rule 403 because its probative value was not substantially outweighed by the danger of unfair prejudice. When the prior conviction evidence was later admitted at trial, the court instructed the jury that it could consider the evidence to the extent that it was •relevant in proving intent or modus oper-andi, but the fact that Henry may have committed a prior crime did not prove that he committed either of the charged crimes.

The court also rejected Henry’s effort at trial to block the government from offering certain expert testimony by a police officer. The officer testified that he had experience investigating drug trafficking as a member of the Drug Control Unit of the Boston Police Department, where he had participated in over 100 drug buys, listened to wiretapped conversations, and instructed other officers on drug trade practices. During the trial, he testified that texts on Henry’s cell phone containing terminology such as “flav,” “dub,” “hard,” “plays,” “bus[t]ing a move,” and “7 to a 14 lg” referred to drug transactions. These opinions were inadmissible, Henry argued, because they were speculative or within the ken of the average juror. The officer also opined that, “looking at everything, the large amount of money, looking at the booking sheet without any employment, apparently, the large amount of drugs, the way that they’re packaged, all similar in size and packaging, ... putting it all together, in [his] opinion, these drugs were packaged for sale.” Henry claimed that this opinion should be excluded pursuant to Rule 704(b) of the Federal Rules of Evidence as an impermissible opinion on intent.

Henry’s primary theory of defense was that the officers lied in claiming that they had found drugs on him during-the search. He also sent mixed signals as to whether he planned to challenge the government’s contention that he possessed the drugs with an intent to distribute. Prior to trial, he informed the court that he would be contesting possession but not intent. He stated in his opening statement that “[i]t may very well be that the packaging and the amount of cocaine in those bags was intended for distribution, but what you’re going to learn is that Henry didn’t, possess it.” He also submitted a proposed jury instruction prior to trial, however, that asked the court to instruct the jury on the lesser included offense of simple possession.

The day before closing arguments, Henry renewed his request for a simple possession instruction. Although the judge agreed to consider the issue further, she told Henry that he should assume that she would not give his proposed instruction. The next morning, the judge informed counsel that she had looked into case law and determined that it would not be rational for a jury to find simple possession. On that basis, she told counsel that she would not give a lesser included instruction. She also stated, “Counsel, your objection as to that is noted for the record.” Before bringing in the jury, the judge again stated, “I’m not going to give the lesser included instruction, and I addressed that on the record.”

The jury instructions were split into two parts: the jury was given preliminary instructions, each party gave its closing argument, and then the jury was given the remaining instructions, which did not include a charge on simple possession. Following this last set of instructions, the judge met with counsel at sidebar. The government stated that it did not object to the charge, and Henry’s counsel declared that there was “[njothing from ... the defense.”

The jury convicted Henry of the drug charge, but acquitted him of the firearm charge. This appeal followed.

II. ANALYSIS

Henry challenges his conviction by claiming that (1) the warrant authorizing the search of his cell phone was not supported by probable cause; (2) the court erred in admitting evidence of his prior drug conviction; (3) a police expert was permitted to offer inadmissible opinion testimony; and (4) Henry was entitled to a jury instruction on the lesser included offense of simple possession. We address each argument in turn.

A. The Search of Henry’s Cell Phone

Henry first challenges the denial of his motion to suppress the evidence obtained from his cell phone. Athough his opening brief argues that the warrant to search his cell phone was not supported by probable cause, it inexplicably fails to address the district court’s alternative basis for denying the suppression motion: that, even if probable cause was lacking, the good-faith exception to the exclusionary rule applied. See United States v. Leon, 468 U.S. 897, 920-23, 104 S.Ct. 3405, 82 L.Ed.2d 677 (1984). By failing to address the good-faith- exception in his opening brief, Henry waived any argument that it is inapplicable in his case. See United States v. Casey, 825 F.3d 1, 12 (1st Cir. 2016) (“[Arguments raised for the first time in an appellate reply brief [are] ordinarily deemed waived....”); United States v. Stevens, 380 F.3d 1021, 1024-25 (7th Cir. 2004) (concluding that defendant waived argument that good-faith exception did not apply where defendant’s opening brief argued that affidavit in search warrant application failed to establish probable cause but “failed to attack the court’s alternative holding that the evidence seized was admissible under the good-faith exception to the exclusionary rule”); see also United States v. Fox, 363 Fed.Appx. 375, 376-77 (6th Cir. 2010) (unpublished) (same).

Henry concedes that his failure to address the good-faith exception in his opening brief waived that argument, but implores us to excuse his waiver. We decline to do so. No extraordinary circumstance explains Henry’s failure to address this issue. Instead, this is a garden-variety failure to raise an argument in an opening brief, and excusing Henry’s failure in these circumstances would turn our venerable raise-or-waive rule into a toothless tiger.

Henry’s failure to preserve for our review any challenge to the district court’s alternative' basis for denying the motion to suppress leaves us no choice but to affirm. See Fox, 363 Fed.Appx. at 377 (“Since the district court’s ruling on the good faith exception sufficed to justify its denial of Fox’s motion to suppress, Fox’s failure to appeal that aspect of the court’s decision means the denial of the motion still stands.”); cf. Sparkle Hill, Inc. v. Interstate Mat Corp., 788 F.3d 25, 29-30 (1st Cir. 2015) (explaining that “[o]ur precedent is clear: we do not consider arguments for reversing a decision of a district court when the argument is not raised in a party’s opening brief’ and applying that rule where-“the opening brief present[ed] no argument at all challenging [the] express grounds upon which the district court prominently relied in entering judgment”). Because we affirm the denial of the motion to suppress solely on the basis of Henry’s waiver, we need not — and therefore do not — express any opinion on whether the warrant was supported by^ probable cause or whether the good-faith exception applies in this case.

B. Henry’s Prior Drug Conviction

A proposal by the government to introduce evidence of a defendant’s prior criminal conduct is subject to a two-part test. See United States v. Hicks, 575 F.3d 130, 142 (1st Cir. 2009). “First, a court must ask whether the proffered evidence has a ‘special’ relevance, i.e., a non-propensity relevance.” Id Under Rule 404(b), “[ejvidence of a crime ... is not admissible to prove a person’s, character in order to show that on a particular occasion the person acted in accordance with the character.” Fed. R. Evid. 404(b)(1). But such evidence “may be admissible for another purpose, such as proving motive, opportunity, intent, preparation, plan, knowledge, identity, absence of mistake, or lack of accident.” Fed. R. Evid. 404(b)(2). If prior crime evidence has special relevance under Rule 404(b), the court must move on to consider whether the evidence should nevertheless be excluded under Rule 403. Hicks, 575 F.3d at 142. Rule 403 provides that “[t]he court may exclude relevant evidence if its probative value is substantially outweighed by a danger of ... unfair prejudice.” Fed. R. Evid.- 403. We review the district court’s admission of a prior conviction under Rules 404(b) and 403 for an abuse of discretion. See United States v. Gemma, 818 F.3d 23, 35 (1st Cir. 2016).

Henry claims that his prior drug conviction was relevant only to prove that he had a propensity to sell drugs. Thus, he argues that the evidence should have been excluded pursuant to Rule 404(b). In the alternative, he contends that the court should have excluded the evidence pursuant to Rule 403 because its prejudicial effect substantially outweighed its probative value. We find that the district court did not abuse its discretion in admitting the prior conviction.

Rule 404(b)(2) specifically permits the admission of a prior conviction to prove intent, and we have repeatedly upheld the admission of prior drug dealing by a defendant to prove a present intent to. distribute. See, e.g., United States v. Manning, 79 F.3d 212, 217 (1st Cir. 1996) (finding no abuse of discretion because “when charges of drug trafficking are involved, this [C]ourt has often upheld the admission of evidence of prior narcotics involvement to prove knowledge and intent.... The evidence that Manning had previously sold cocaine makes it more likely ... that he intended to distribute the two bags of cocaine.”); United States v. Nickens, 955 F.2d 112, 124-25 (1st Cir. 1992) (collecting cases) (“[T]his circuit has repeatedly held that a prior involvement with drugs is admissible to prove knowledge and intent. ... [T]he jury may have [permissibly] inferred that persons who have distributed cocaine in California, are more likely than those who have not, to want to import cocaine from Ecuador.”); United States v. Doe, 741 F.3d 217, 230 (1st Cir. 2013) (citing Manning and noting that prior drug sale “makes it more likely” that defendant intended to sell drugs on later occasion); see also, e.g., United States v. Robinson, 809 F.3d 991, 997 (8th Cir. 2016) (noting that prior conviction for drug distribution is admissible under Rule 404(b) to show intent to commit later charge of conspiracy to distribute drugs); United States v. Lee, 573 F.3d 155, 166 (3d Cir. 2009) (“Lee’s prior drug trafficking conviction was properly admitted as evidence that Lee intended to distribute any drugs in his possession.”).

Henry attempts to distinguish these cases by noting that his theory of defense centered on possession rather than intent. A defendant’s failure to argue lack of knowledge or intent, however, does not “remove those issues from the case.” United States v. Pelletier, 666 F.3d 1, 6 (1st Cir. 2011) (quoting United States v. Ferrer-Cruz, 899 F.2d 135, 138 (1st Cir. 1990)). The burden of proving intent remained on the government, even though Henry did not aggressively litigate the issue, and Henry’s prior conviction had probative value in establishing this element of the charged offense. Accordingly, the district court did not abuse its discretion in ruling that the prior-conviction evidence qualified under the intent exception to Rule 404(b).

We pause to note that this conclusion is compelled by the combination of our deferential standard of review and our precedent. The government appears to argue that evidence of a prior drug distribution offense is always relevant under Rule 404(b) to show knowledge and intent in a prosecution for possession of a controlled substance with intent to distribute. As the concurring opinion explains, this across-the-board position seems to overlook that, in' many cases, impermissible propensity reasoning lurks as one of the links in the logical chain of relevance. Although we discern no abuse of discretion in this case given our precedent, we encourage district court judges to carefully consider the proponent’s assertion of why a prior conviction has special relevance and examine whether, in the particular case-specific circumstances, the proponent is simply attempting to disguise propensity evidence by artificially affixing it with the label of a permitted Rule 404(b)(2) purpose.

Unlike Rule 404(b), which focuses exclusively on whether prior bad act evidence has “special relevance,” Rule 403 requires a balancing of probative value and prejudicial effect. When assessing the probative value of evidence under Rule 403, a court must consider both whether the evidence has been offered to prove an issue that is in genuine dispute, and whether the evidentiary point can be made with other evidence that does not present a risk of unfair prejudice. See United States v. Ford, 839 F.3d 94, 109-10 (1st Cir. 2016); United States v. Varoudakis, 233 F.3d 113, 122-24 (1st Cir. 2000). On the other side of the scale, similarity between the defendant’s prior criminal conduct and the charged offense, which may support a finding of “special relevance” under Rule 404(b), increases the risk that the jury will draw an improper inference of propensity that unfairly prejudices the defendant’s case. Varoudakis, 233 F.3d at 123. In cases such as Henry’s, where a prior drug conviction is offered to prove an intent to distribute drugs on a different occasion, the risk that the jury will use the conviction to infer criminal propensity is especially strong. Courts thus must be alert to this danger when they weigh the prejudicial effect of evidence against its probative value.

In the present case, although Henry did not make the absence of an intent to distribute the centerpiece of his defense, he did raise the issue by seeking a lesser included offense instruction for simple possession. Under these circumstances, the government was entitled to marshal all of its evidence on the issue of intent, including evidence of Henry’s prior criminal conviction, in an effort to demonstrate that the evidence on that element was sufficient to prevent Henry from obtaining a jury instruction on a reduced charge. Moreover, although the similarity between Henry’s prior drug conviction and the charged drug crime presents a risk that the jury might draw an impermissible inference of propensity, the court addressed that risk with a limiting instruction. Given this instruction, the sufficiency of which Henry did not challenge, we cannot say that the district court abused its discretion in rejecting Henry’s claim that the prejudicial effect of the prior crime evidence substantially outweighed its probative value. In short, this is not the rare case where we are prepared to second-guess the district court’s Rule 403 analysis.

Having determined that the district court properly admitted evidence of Henry’s past criminal conduct to prove intent, we need not determine whether the same evidence could have been admitted independently to prove modus operandi. Instead, the real issue is whether the district court committed reversible error in instructing the jury that evidence that was properly admitted for one purpose could also be considered for a different, arguably inadmissible, purpose. Errors of this sort are harmless if it is “highly probable that the error did not influence the verdict.” Hicks, 575 F.3d at 143 (quoting United States v. Roberson, 459 F.3d 39, 49 (1st Cir. 2006)).

Here, the record contains ample evidence to support the verdict. Moreover, as we have explained, the court permissibly admitted Henry’s prior conviction for a different purpose and instructed the jury that it could not be used to infer criminal propensity. Nothing in the facts or argument at trial pointed to a finding of modus operandi as a pathway to a guilty verdict that was not far more likely to have been provided by a finding of intent. Under these circumstances, if the court erred in instructing the jury that it could also consider Henry’s prior conviction as evidence of modus operandi, the error was harmless. Cf. United States v. Levy-Cordero, 67 F.3d 1002, 1011 (1st Cir. 1995) (erroneous instruction that jury could consider prior bad act evidence to show intent or knowledge was harmless where evidence was admissible to show consciousness of guilt).

C. Expert Witness Testimony

Henry complains that the district court improperly admitted expert testimony from a police officer. We review the court’s rulings on this issue for abuse of discretion. See United States v. Jordan, 813 F.3d 442, 445 (1st Cir. 2016), cert. denied, — U.S.-, 136 S.Ct. 2528, 195 L.Ed.2d 855 (2016); United States v. Schneiderhan, 404 F.3d 73, 81 (1st Cir. 2005).

“[W]e have long held that government witnesses with experience in drug investigations may explain the drug trade and translate coded language for juries, either through lay or, if qualified, expert testimony.” United States v. Rosado-Pérez, 605 F.3d 48, 56 (1st Cir. 2010). “This [C]ourt has repeatedly found no abuse of discretion in the admission of ... expert testimony to explain the typical methods of drug dealers.” United States v. Monell, 801 F.3d 34, 45 (1st Cir. 2015). This is because police officers’ interpretations of the jargon used within criminal circles may “give the jury the benefit of an independent body of specialized knowledge.” United States v. Albertelli, 687 F.3d 439, 446 (1st Cir. 2012). Officers may also interpret the slang terminology used by drug dealers. United States v. Santiago, 566 F.3d 65, 69 (1st Cir. 2009).

Notwithstanding this formidable body of precedent, Henry presents two challenges to the police expert’s testimony. First, he argues that the court violated Rule 704(b) of the Federal Rules of Evidence by allowing the expert to express an opinion as to whether Henry possessed the drugs with an intent to distribute. Second, he argues that the court should have barred the expert from interpreting his text messages because the expert’s interpretations were either speculative or within the ken of the jury. We find no reversible error.

1. Rule 704(b) Claim

Rule 704(b) provides that “[i]n a criminal case, an expert witness must not state an opinion about whether the defendant did or did not have a mental state or condition that constitutes an element of the crime charged.” Fed. R. Evid. 704(b). “Those matters are for the trier of fact alone.” Id. Here, Henry concedes that the police expert “did not explicitly state that he believed that Henry had the intent to distribute drugs.” Instead, he argues that “the import of’ the testimony was improper because it implied that Henry acted with culpable intent. Henry focuses on the following exchange during direct examination:

Q. Sir, do you have an opinion based on your training and experience considering all of the evidence in this particular case and the reports that you read and your conversations you’ve had as to whether it is consistent with the [sic] distribution or personal use?
A. Yes. It’s my opinion, looking at everything, the large amount of money, looking at the booking sheet without any employment, apparently, the large amount of drugs, the way that they’re packaged, all similar in size and packaging, also looking at — you know, putting it all. together, in my opinion, these drugs were packaged for sale.

According to Henry, the expert’s opinion that “these drugs were packaged for sale” was impermissible under Rule 704(b) because it implies an answer to a question that is reserved exclusively for the jury.

We conclude that the district court did not abuse its discretion in admitting the expert’s opinion. Rule 704(b) bars a witness from characterizing the defendant’s intent, but it “does not, however, apply to ‘predicate facts from which a jury might infer such intent.’ ” United States v. Peña-Santo, 809 F.3d 686, 694 (1st Cir. 2015) (quoting Schneiderhan, 404 F.3d at 81), petition for cert. docketed sub norm Gil-Martinez v. United States, No. 16-6836, — U.S. -, 137 S.Ct. 680, 196 L.Ed.2d 563, 2017 WL 69579 (U.S. Nov. 14, 2016). In this case, the expert grounded his opinion that the drugs were packaged for sale on his general knowledge of criminal practices and the circumstantial evidence bearing on the issue of intent that was produced during the trial. He did not attempt to offer any special insight as to Henry’s actual mental state. Accordingly, the expert’s testimony is consistent with prior precedent, which recognizes that a qualified expert does not violate Rule 704(b) by expressing an opinion as to whether predicate facts are consistent with drug distribution rather than mere possession. See United States v. Valle, 72 F.3d 210, 216 (1st Cir. 1995). Even if the jury interpreted the expert’s testimony to be responsive to the prosecutor’s question and not merely to be an opinion about how the drugs were packaged, as Henry posits, the phrasing of that question was permissible. We have upheld expert testimony that certain facts were “consistent with” distribution. See id.

2. Text Messages

As recounted above, our cases make it clear that a qualified expert may opine as to the meaning of criminals’ coded communications. See, e.g., Rosado-Pérez, 605 F.3d at 55-56; Albertelli, 687 F.3d at 446; Santiago, 566 F.3d at 69. Henry does not ask us to overrule our precedents, nor does he contest the officer’s qualifications as an expert. Rather, he argues that “[t]he messages contain perhaps two words (‘hard’ and ‘flav’) that could be considered specialized language requiring some explanation.” The remaining messages, he contends, “were normal, uncoded language that the jurors could read and interpret on their own.” We find no abuse of discretion.

First, many of the text messages contain specialized language whose meaning an expert might helpfully illuminate. For example, the words “flav” and “dub” are jargon inaccessible to many jurors. See Santiago, 566 F.3d at 68-69 (interpreting “chef it up” as slang for “converting cocaine into crack”). Similarly, the use of ordinary words — e.g., “hard,” “work,” “plays,” “7 to a 14 lg,” and “bus[t]ing a couple moves”— in an idiosyncratic way rendered them meaningless to laypersons. The witness shed light on contextual meanings for these words, which undoubtedly “help[ed] the trier of fact to understand the evidence or to determine a fact in issue.” See Fed. R. Evid. 702(a). '

Second, the officer’s interpretation of other text messages that did not contain obscure jargon was nonetheless permissible because he drew upon his expertise in explaining the relevance of the communications in the drug trade. For example, he discussed an exchange in which Henry’s interlocutor indicates that Henry has several cell phones and asks to borrow one. The officer drew upon his extensive experience in explaining the significance of this exchange, by noting that dealers often use multiple phones, each for a different purpose. Such explanations are based upon his expertise and are helpful to the jury, which may be unaware of the inner workings of the drug trade.

Third, any danger posed by the testimony was substantially mitigated by cross-examination and the district court’s limiting instruction. Once an expert testifies, “[f]rom that point forward, the credibility and weight of the expert’s opinion [is] for the factfinder.” Jordan, 813 F.3d at 446. The jury’s task is to “independently evaluate [his] interpretations,” and the defendant’s task is to “exhaustively cross-examine! ] [the witness] about possible alternative interpretations.” See Rosado-Pérez, 605 F.3d at 56. Here, Henry sought to undermine the witness’s testimony by cross-examining him on alternative interpretations. For example, Henry effectively cross-examined the witness on the meaning of “bus[t]ing a move” by prompting the officer to recall the lyrics of a popular song that uses the same phrase in a manner unrelated to drug' dealing. The danger posed by questionable testimony was also mitigated by the district court’s instruction to the jury that it should weigh the evidence independently. See Albertelli, 687 F.3d at 448-49.

For these reasons, the district court did not commit reversible error in allowing the police expert to testify.

D. Lesser Included Instruction

Henry faults the district court for failing to instruct the jury on the lesser included offense of simple possession. We review a district court’s failure to give a properly requested jury instruction de novo, but examine an unpreserved request only for plain error. United States v. Meadows, 571 F.3d 131, 145-46 (1st Cir. 2009). Before turning to the merits of Henry’s argument, we first consider the government’s contention that the court’s failure to instruct the jury on simple possession is subject to plain error review because Henry failed to renew his objection with the court after the charge was read.

1. Failure to Properly Object

Rule 30 of the Federal Rules of Criminal Procedure requires a party who objects to the court’s failure to give a proposed instruction to inform the court of his objection “before the jury retires to deliberate.” Fed. R. Crim. P. 30(d). The text of Rule 30(d) is silent regarding the earliest point at which a party may object so as to preserve the issue for appeal, but our decisions have ordinarily required the appellant to renew his objection after the jury has been charged when the court has given the parties that opportunity. See Gemma, 818 F.3d at 38; Meadows, 571 F.3d at 146; United States v. O’Connor, 28 F.3d 218, 221 (1st Cir. 1994). We have also determined that this rule is “binding on both the court and attorney and that a statement by the court ‘after the charge that objections made prior to it will be saved does not absolve the attorney from following the strictures of the rule.’ ” O’Connor, 28 F.3d at 221 (quoting Poulin, 18 F.3d at 982).

Henry attempts to avoid this precedent by invoking our decision in United States v. Kaplan, 832 F.2d 676, 682 (1st Cir. 1987). Kaplan, however, cannot save Henry from failing to properly preserve his objection. Unlike in this case, the defendant in Kaplan renewed his request for an instruction following the jury charge, but simply did not “repeat the magic word ‘objection.’ ” See Kaplan, 832 F.2d at 682. Finding that our precedents did not require the strict use of that word, we determined that the objection had been preserved. See id. Here, in contrast, Henry did not make any attempt to preserve his objection after the charge was read.

Henry also correctly notes that there are circumstances where “a court should not require a lawyer ‘to persist stubbornly when the judge has made it perfectly clear that he does not wish to hear what the lawyer has to say.’ ” United States v. Fernández-Garay, 788 F.3d 1, 4 (1st Cir. 2015) (quoting United States v. Toribio-Lugo, 376 F.3d 33, 41 (1st Cir. 2004)). Henry, however, did not face those circumstances. He cannot plausibly argue that he “had no reasonable opportunity” to object. Cf. Fernández-Garay, 788 F.3d at 4 (Rule 51 objection preserved where judge abruptly cut short defense counsel and forbade him from continuing). Immediately following the jury charge, but before deliberations, the district court invited counsel to sidebar. The prosecution informed the court that it had “no objection” to the instructions, and Henry stated that there was “[n]othing from ... the defense.” Henry was required to object here. After being invited to sidebar, he would not have “affront[ed] the court or prejudiee[d] the jury beyond repair” by respectfully renewing his objection. See Toribio-Lugo, 376 F.3d at 41 (quoting Douglas v. Alabama, 380 U.S. 415, 422, 85 S.Ct. 1074, 13 L.Ed.2d 934 (1965)).

In the present case, the district court invited the parties to approach the bench after it completed its instructions in an obvious effort to permit the parties to register their objections to the jury charge. Henry did not present any objections in response to this invitation. Accordingly, his claim that the court erred in failing to instruct the jury on simple possession is reviewed only for plain error. See Meadows, 571 F.3d at 146.

2. Simple Possession Instruction

A failure by the district court to give a proposed jury instruction will qualify as plain error only if the defendant demonstrates that “(1) an error occurred; (2) which was clear or obvious; and both (3) affected [his] substantial rights; and (4) seriously impaired the fairness, integrity, or public reputation of judicial proceedings.” Gemma, 818 F.3d at 30 (alteration in original) (quoting United States v. Laureano-Pérez, 797 F.3d 45, 60 (1st Cir. 2015)). “This standard is exceedingly difficult to satisfy in jury instruction cases: ‘[T]he plain error hurdle, high in all events, nowhere looms larger than in the context of alleged instructional errors.’ ” Meadows, 571 F.3d at 145 (quoting United States v. González-Vélez, 466 F.3d 27, 35 (1st Cir. 2006)).

Henry cannot satisfy the plain error test because he is unable to show that his substantial rights were affected by the court’s refusal to instruct on simple possession. To satisfy this requirement, a défendant must establish “a reasonable probability that, but for [the error claimed], the result of the proceeding would have been different.” United States v. Rodríguez, 735 F.3d 1, 11 (1st Cir. 2013) (alteration in original) (quoting United States v. Hebshie, 549 F.3d 30, 44 (1st Cir. 2008)). Henry fails to present a persuasive argument that the jury might have acquitted him of the possession with intent to distribute charge if it had been instructed on the lesser included offense of simple possession given that: the record contains no affirmative evidence that Henry possessed the drugs for personal use; Henry’s intent to distribute was minimally contested and nearly conceded at trial; the quantity of drugs Henry carried was consistent with an intent to distribute; Henry was carrying a large amount 'of cash denominated at the street purchase price for crack cocaine; and Henry’s text messages suggested that he was a dealer of drugs rather than a mere user. Accordingly, the district court did not commit plain error in refusing to instruct on the lesser included offense of simple possession. Cf. United States v. Henson, 945 F.2d 430, 440-41 (1st Cir. 1991) (holding that failure to give lesser included offense instruction was not “error of sufficient magnitude to overcome the ‘high hurdle’ interposed by the plain error rule” where uncontroverted evidence was sufficient to establish additional elements of greater offense).

III. CONCLUSION

For the reasons stated, Christopher Henry’s conviction and sentence are affirmed.

KAYATTA, Circuit Judge,

with whom THOMPSON, Circuit Judge, joins, concurring.

Because the court’s opinion well marshals our controlling precedent in support of its conclusions, I join in full. I write separately only to note that the admission of evidence of a prior conviction to establish the “intent” of the defendant in connection with the offense being tried can become indistinguishable from the admission of evidence of a prior conviction to prove a propensity to commit that type of crime.

The opinion for the court relies on our prior opinion in United States v. Manning, 79 F.3d 212, 217 (1st Cir. 1996) to approve the admission of a prior drug distribution conviction to prove the element of intent in this later drug distribution case. There is reason to think, though, that the inference that Manning licensed in this case, and in drug cases of this sort, is contrary to Federal Rule of Evidence 404(b). See United States v. Miller, 673 F.3d 688, 699 (7th Cir. 2012) (“How, exactly, does [the (defendant’s] prior drug dealing conviction in 2000 suggest that he intended to deal drugs in 2008? When the question is framed this way, the answer becomes obvious, even though implicit: ‘He intended to do it before, ladies and gentlemen, so he must have intended to do it again.’ That is precisely the forbidden propensity inference.”); United States v. Turner, 781 F.3d 374, 390-91 (8th Cir.) (similar), cert. denied, — U.S. -, 136 S.Ct. 208, 193 L.Ed.2d 160 (2015), cert. denied, — U.S. -, 136 S.Ct. 280, 193 L.Ed.2d 204 (2015), and cert. denied, — U.S.-, 136 S.Ct. 493, 193 L.Ed.2d 359 (2015).

This case illustrates the manner in which the relevance of a prior conviction admitted to prove “intent” under Manning may rest on little more than propensity. In its brief, the government did not articulate how Henry’s prior conviction was relevant to whether he intended to distribute the crack cocaine found in his pocket on May 29, 2014. At oral argument, the government posited that the prior conviction was relevant to Henry’s intent because the fact that Henry possessed fourteen separately packaged rocks of crack cocaine with the intent to, distribute them in March 2011 implies that he- intended to distribute the twenty-one separately packaged rocks of crack cocaine he possessed in May 2014. This reasoning is propensity-based. It requires inferring from Henry’s prior conviction that he has the following character trait: whenever he possesses separately packaged rocks of crack cocaine, he intends to distribute them. That is, his propensity is to be a seller, rather than a. buyer or user. It then requires inferring that he acted in accordance with that character trait in May 2014. The admission of Henry’s prior conviction on this line of reasoning, although allowed by Manning, appears to run afoul of Rule 404(b)(1), which bars the use of other acts evidence “to prove a person’s character in order to show that on a particular occasion the person acted in accordance with the character.”

For the foregoing reasons, one can make a good argument for going en banc in a future case .to reconsider our Rule 404(b)(1) jurisprudence. I say “future” case because, in this particular case, any Rule 404(b) error was harmless given the overwhelming evidence of Henry’s guilt.

The main argument for not revisiting Manning at some point (assuming one thinks it may be wrong) is that it might not be worth the effort, given that in drug cases of this sort, prior convictions are often admitted for multiple reasons. For instance, in many cases, prior convictions are admitted to show both knowledge of the nature of a substance and intent to distribute. See, e.g., United States v. Doe, 741 F.3d 217, 230 (1st Cir. 2013); United States v. Pelletier, 666 F.3d 1, 6 (1st Cir. 2011); United States v. Hicks, 575 F.3d 130, 142 (1st Cir. 2009); United States v. Landrau-López, 444 F.3d 19, 24 (1st Cir. 2006); United States v. Nickens, 955 F.2d 112, 123-24 (1st Cir. 1992) (collecting cases). Commonly, there are chains of inference from a prior conviction to knowledge that do not include propensity as a necessary link. See, e.g., United States v. Arias-Montoya, 967 F.2d 708, 710-11 (1st Cir. 1992) (discussing several prior cases where prior convictions were admitted on knowledge grounds); United States v. Ferrer-Cruz, 899 F.2d 135, 138 (1st Cir. 1990).

Overruling Manning would nevertheless have three nontrivial effects in cases where the only inferential chains linking a prior conviction to intent to distribute include criminal propensity. First, it would mean that juries in these cases would not be instructed that they could use prior convictions to infer intent. Second, it would mean that the relevance of a prior conviction to intent to distribute would contribute not to the conviction's probative value under Rule 403, but instead to the risk of unfair prejudice. Third, it would allow defendants to keep a prior conviction out of a case without having to stipulate to intent to distribute. These effects would occur even in cases where the prior conviction might be specially relevant on one of the other grounds listed in Rule 404(b)(2).

The third of these effects can be particularly significant. Consider, for example, a case in which a prior drug sale is relevant to knowledge, which happens not to be an element that the defendant desires to challenge. In Ferrer-Cruz, 899 F.2d at 139; United States v. Garcia, 983 F.2d 1160, 1175-76 (1st Cir. 1993); and Pelletier, 666 F.3d at 6, we pointed to the possibility that a defendant may remove an issue like knowledge from a case by tendering an express disavowal and willingness to accept a corresponding limitation on cross-examination and jury instruction. While we have never had occasion to accept or reject such an approach directly in construing Rule 404, certainly the district courts can achieve the same result on their own simply by finding that the presence of such a disavowal and instruction shift the Rule 403 balance against admission. Manning complicates such an approach because it effectively requires a stipulation on intent as well in order to eliminate fully the Rule 404(b)(2) toehold for admitting the evidence. Of course, even under Manning, trial courts have ample room to keep out such evidence under Rule 403 even in the absence of a stipulation on intent. As this case shows, though, sometimes they do not exercise that discretion in this manner.

      . The district court enhanced Henry’s sentence based on a finding by a preponderance of the evidence that he possessed a gun during the commission of his drug crime. Henry complains that the enhancement violated his constitutional rights under the Fifth and Sixth Amendments because it was based on acquitted conduct. We decline to consider this argument because, as Henry acknowledges, his argument is foreclosed by Supreme Court and First Circuit case law. See United States v. Watts, 519 U.S. 148, 149, 117 S.Ct. 633, 136 L.Ed.2d 554 (1997) (per curiam); United States v. Alejandro-Montañez, 778 F.3d 352, 361 (1st Cir. 2015).

      . The Supreme Court has held that a stipulation to felon status, when it is an element of a charged crime, does not eliminate the relevance of a prior conviction to that element, but merely impairs its probative value under Rule 403. See Old Chief v. United States, 519 U.S. 172, 179, 117 S.Ct. 644, 136 L.Ed.2d 574 (1997) ("[The] evidentiary relevance [of Old Chief’s prior conviction] under Rule 401 [was not] affected by the availability of alternative proofs of the element to which it went, such as an admission by Old Chief....”); id. at 18 4, 117 S.Ct. 644 ("[W]hat counts as the Rule 403 ‘probative value of an item of evidence, as distinct from its Rule 401 ‘relevance,’ may be calculated by . comparing evidentiary alternatives.”). There is room to debate both whether this reasoning from Old Chief applies to prior convictions introduced for one of the purposes listed in Rule 404(b)(2) and whether its holding as to relevance applies to so-called "special relevance” under Rule 404(b). Compare United States v. Crowder, 141 F.3d 1202, 1206-07 (D.C. Cir. 1998) (en banc), with id. at 1212-13 (Tatel, J., dissenting).


author: DYK, Circuit Judge.

text:
    UNITED STATES of America, Appellee, v. Nelson PEREIRA, Defendant, Appellant.
    No. 15-1669
    United States Court of Appeals, First Circuit.
    February 3, 2017

      James L. Sultan, with whom Kerry A. Haberlin and Rankin & Sultan, Boston, MA, were on brief, for appellant.
    Olga B. Castellón-Miranda, Assistant United States Attorney, Criminal Division, with whom Rosa E. Rodríguez-Vélez, United States Attorney, Mariana E. Bau-zá-Almonte, Assistant United States Attorney, Chief, Appellate Division, and Juan Carlos Reyes-Ramos, Assistant United States Attorney, were on brief, for appel-lee.
    Before THOMPSON, DYK, and KAYATTA Circuit Judges.

       Of the Federal Circuit, sitting by designation.

   DYK, Circuit Judge.

Nelson Pereira was convicted of conspiring to" possess cocaine with the intent to distribute, and aiding and abetting others to possess cocaine with the intent to distribute, in violation of 18 U.S.C. § 2 and 21 U.S.C. §§ 841(a)(1), 846. On appeal, Pereira contends that a new trial is warranted as a result of, inter alia, the prosecutor’s improper questioning that compelled him to comment on the veracity of two cooperating government witnesses, a problem that was exacerbated by improper judicial intervention in support of the prosecutor’s questions. For the. reasons that follow, we vacate Pereira’s conviction and remand for a new trial.

I.

Pereira does not challenge the legal sufficiency of the evidence supporting his conviction, and in such situations, there is a “lack of clear consensus in this circuit whether to recite the facts in the light most favorable to the verdict.” United States v. Vázquez-Larrauri, 778 F.3d 276, 280 (1st Cir. 2015). Because the manner of review of the facts would make no difference to this appeal, we elect to present them in a neutral and balanced way.

This ease stems from a conspiracy to smuggle drugs from Puerto Rico into the continental United States. The government’s evidence established the following. A group led by Wilfredo Rodríguez-Rosa-do (“Rodríguez”) conspired to transport drugs and drug-trafficking proceeds in luggage onboard American Airlines (“AA”) flights between San Juan, Puerto Rico, and Newark, New Jersey. Many of the co-conspirators were AA employees with baggage handling responsibilities and who had knowledge of airport security as well as access to nonpublic airport areas. Rodriguez masterminded the scheme from Puer-to Rico, while Frank Prats (“Prats”), an AA employee at Newark Liberty International Airport, oversaw the Newark side of the operation.

The scheme( involved packaging drugs or drug proceeds inside suitcases, smuggling these suitcases aboard AA flights, and relaying the flight information and suitcase location to conspirators at the destination airport. These conspirators would then arrange for the suitcases’ unloading into the baggage claim area for pickup by other previously instructed conspirators. This conspiracy began sometime in 1999 and continued for a decade, until September 2009, when authorities arrested and indicted numerous conspirators. These arrests subsequently yielded additional evidence against other individuals who were not initially indicted, including defendant Pereira.

On March 15, 2013, Pereira was indicted for conspiring to possess cocaine with intent to distribute in violation of 21 U.S.C. §§ 841(a)(1), 846, and for aiding and abetting possession of cocaine with the intent to distribute in violation of 21 U.S.C. § 841(a)(1) and 18 U.S.C. § 2.

Pereira, who worked at Newark Airport, was alleged to have participated in this conspiracy by orchestrating the baggage handling at Newark to ensure that the drug suitcases were properly picked up upon arrival, by giving instructions to the co-conspirators making the pickups, and by stepping in for Prats when he was unavailable to receive instructions and payments from Rodriguez.

At trial, the primary evidence against Pereira came from two cooperating government witnesses, Gerardo Torres-Rodriguez (“Torres”) and Javier Olmo-Rivera (“Olmo”). These individuals had previously pleaded guilty to participating in the conspiracy. Torres’s role in the conspiracy was to receive money and make payments in Puerto Rico, to relay the flight and suitcase information from Puerto Rico to the Newark conspirators (Prats and Per-eira) once the flights had departed San Juan, and, on a few occasions, to fly to Newark with suitcases containing cocaine and to bring back suitcases containing money. Olmo’s role in the conspiracy was to physically transport on his person drugs or monies onboard AA flights and to prepare the cocaine for shipments from San Juan to Newark. Torres and Olmo both testified that Pereira was the right-hand man of Prats (who oversaw the Newark operations), with a crucial role in the conspiracy to ensure the smooth pickup of the drug suitcases at Newark, as well as providing and receiving instructions and payments to and from co-conspirators. Torres testified specifically that Pereira had once allowed him access to the AA locker room to exchange a bag of drug money. Olmo testified specifically that Pereira had warned a co-conspirator against picking up a drug suitcase on one occasion due to law-enforcement monitoring, and that Pereira had traveled to Puerto Rico to meet with Rodriguez to provide AA luggage tags for use in furtherance of this conspiracy.

Beside the testimony of Torres and Olmo, the government’s sole evidence connecting Pereira to the conspiracy was a piece of Prats’s stationery containing Per-eira’s first name and phone number and evidence that Pereira took an unusually short trip to Puerto Rico (supporting an inference that it was in furtherance of the conspiracy rather than a vacation). The piece of paper was found during a search of Rodriguez’s house and was used to link Pereira to Rodriguez. Given the lack of other evidence, the credibility of Torres and Olmo was crucial to the government’s case.

During the trial, Pereira testified in his own defense. He admitted knowing Rodriguez and Prats as fellow AA employees, but denied participating in a drug-smuggling conspiracy with them. Pereira also denied knowing Torres or Olmo, or undertaking the actions in furtherance of the conspiracy that they had attributed to him. Pereira did admit to having taken a short trip to Puerto Rico as one of several such short vacations that he enjoyed as an AA employee who received free airfare and discounted hotel rates.

On cross-examination, the prosecutor inquired into the stark discrepancy between Pereira’s testimony and Torres’s and Olmo’s testimony. The central question is whether the prosecutor engaged in improper conduct when he repeatedly asked whether Pereira thought Torres or Olmo had “made up” these allegations as a part of a “setup.”

On April 14, 2014, the jury found Pereira guilty of “[c]onspiraey to possess with the intent to distribute five [ ] kilograms or more of cocaine,” and “[ajiding and abetting in possession with intent to distribute five [ ] kilograms of cocaine,” in violation of 18 U.S.C. § 2 and 21 U.S.C. §§ 841(a)(1), 846. Def. Add. 58. On May 12, 2015, Per-eira was sentenced to 151 months in federal detention, 5 years of supervised release thereafter, and a monetary penalty of $100,200. .

On appeal, Pereira contends that he is entitled to a new trial because the prosecu-torial questions about whether the cooperating government witness testimony was “made up” or was a part of a “setup” improperly compelled Pereira to comment on Torres’s and Olmo’s veracity.

We have jurisdiction pursuant to 28 U.S.C. § 1291. We review preserved objections of prosecutorial misconduct for harmless error. United States v. Carpenter, 736 F.3d 619, 630 (1st Cir. 2013). Under harmless error analysis, “[a] new trial is unwarranted so long as we are able to conclude with a high degree of confidence that the alleged prosecutorial misconduct did not affect the outcome of the trial.” United States v. Smith, 982 F.2d 681, 684 (1st Cir. 1993).

II.

We first address whether the prosecutor engaged in misconduct by asking whether Pereira thought Torres and Olmo had “made up” testimony against him as a part of a “setup.” At oral argument, the government agreed that by asking the defendant whether he thought he was being “set up” by the witness or whether he thought the witness “made up” testimony about the defendant, the prosecutor was effectively asking the defendant whether he thought the government witnesses were lying. See also United States v. Alcantara-Castillo, 788 F.3d 1186, 1192 (9th Cir. 2015) (holding that questions phrased in the form of “making that up” or “inventing stories about you” are equivalent to asking if the witness was lying).

Over the past twenty-five years, this court has consistently held that “counsel should not ask one witness to comment on the veracity of the testimony of another witness.... We expect that the office of the United States Attorney ... will abide by the rule.” United States v. Sullivan, 85 F.3d 743, 750 (1st Cir. 1996) (citations and footnote omitted). Other cases, utilizing similar language, also make the same point. See, e.g., United States v. Thiongo, 344 F.3d 55, 61 (1st Cir. 2003) (“This Court has held it is improper for an attorney to ask a witness whether another witness lied on the stand. Underlying this rule is the concept that credibility judgments are for the jury, not witnesses, to make.” (citation omitted)); United States v. Akitoye, 923 F.2d 221, 224 (1st Cir. 1991) (“[I]t is not the place of one witness to draw conclusions about, or cast aspersions upon, another witness’ veracity. The ‘was-the-witness-lying’ question framed by the prosecutor ... should never [ ] be[ ] posed.” (citations omitted)).

This circuit is not alone in reaching this conclusion. “[M]ost of the federal courts of appeals that have examined the propriety of questions posed to a criminal defendant about the credibility of government witnesses have found that such questions are improper.” United States v. Schmitz, 634 F.3d 1247, 1268 (11th Cir. 2011) (collecting cases). Such “were-they-lying questions invade the province of the jury.” Id. at 1269; see also United States v. Boyd, 54 F.3d 868, 871 (D.C. Cir. 1995) (holding that questions about whether another witness would “make up” testimony impermissibly infringes “on the jury’s right to make credibility determinations”). These types of Questions are also improper because Rule 608(a) of the Federal Rules of Evidence “does not permit a witness to testify that another witness was truthful or not on a specific occasion.” Schmitz, 634 F.3d at 1268. Such questions also “ignore other possible explanations for inconsistent testimony ... [which] put the testifying defendant in a ‘no-win’ situation [of] ... either accusing] another witness of lying or undermining] his or her own version of events.” Id. at 1269. Finally, these “were-they-lying questions are argumentative, and often their primary purpose is to make the defendant appear accusatory.” Id. The danger is that the prosecutor first forces the defendant to label government witnesses as liars who are making up stories, and then, after laying this groundwork, seeks to convince the jury that it is the accusatory defendant — and not the prosecution witnesses — who is unworthy of belief.

In United States v. DeSimone, 699 F.3d 113 (1st Cir. 2012), this court clarified that although

[i]t is improper for an attorney to ask a witness whether another witness lied on the stand[,] ... [i]t is not improper to ask one witness whether another was “wrong” or “mistaken,” since such questions do not force a witness to choose between conceding the point or branding another witness as a liar. There is no error in simply asking a witness if he agreed with or disputed another witness’s testimony.

Id. at 127 (citations and quotation marks omitted); see also United States v. Wallace, 461 F.3d 15, 25 (1st Cir. 2006) (same); Thiongo, 344 F.3d at 61 (same).

Against this background, Pereira contends that by “compelling [him] to comment on Torres’s and Olmo’s veracity[,] ... each instance of prosecutorial misconduct was designed to, and did, unfairly undercut Pereira’s credibility and bolster[ ] that of Torres and Olmo.” Appellant Br. 33-34. He also argues that, under the cumulative-error doctrine, see United States v. Sepulveda, 15 F.3d 1161, 1195-96 (1st Cir. 1993), the errors that occurred at his trial are sufficiently serious in the aggregate to warrant a new trial even if they would not necessitate such relief if viewed individually.

A.

We have excerpted and numbered the relevant question sets below in chronological order. While the excerpts from the testimony are lengthy, setting them out in full provides the necessary context.

Set 1 of the prosecutor’s questions related to Pereira’s denial of any knowledge of or connection to Torres. The prosecutor asked, on cross-examination, why, if that was the case, Torres would have had a photograph of Pereira (as Torres had earlier testified). JA 1055-59.

Q. Do you have any idea why Gerardo Torres ... would have this picture of you? Do you have any idea?
A. I can’t answer why, but I can answer how.... He went to my Facebook account, and that’s my profile picture.
Q. My question is: Do you have any idea why Gerardo Torres would be going to your Facebook page? ... Do you know why?
Defense: Your Honor, this is calling for speculation. The witness is not here. He’s asking for what the other person thought, what the other person wanted. That’s beyond the direct.
Court: I don’t think it’s beyond the direct. I’ll allow the question.
Q. Do you? .... Do you have think [sic] idea why Gerardo Torres would be going • to your Facebook page and getting your photo off your page?
Defense: That’s calling for speculation, Your Honor, “Do you have any idea?” That’s an improper question.
Q. Do you know why?
Court: Do you know?
A. The only reason why is probably to set me up.
Q. So he set you up?
A. Yes.
Q. Okay. And he set you up back in 2010 prior to your arrest in this case; right?
A. I guess.
Q. So it was part of an elaborate plan to set you up; right?
A. I cannot answer for him.
Q. But you have no idea why Gerardo Torres would have gotten your photo other than to set you up; right?
Defense: Objection, Your Honor. It’s calling also for speculation. What ideas—
Court: He already said it was to set him up. Overruled.
Q. Right?
Court: Other than that reason, there’s no other reason why Mr. Torres would get your picture off Facebook. That’s the question. That you know of.
A. I don’t know what he was thinking.

Set 2 related to Torres’s testimony that his- interactions with Pereira during the conspiracy entailed calling Pereira about the flight information for the smuggled drug suitcases, and that Pereira was Prats’s trusted helper in handling the drug suitcases. JA 1088-92.

Q. During the years 2001 to 2005, you never received a call from Gerardo Torres pertaining to suitcases full of drugs. Correct? That’s your testimony?
A. That’s correct.
Q. So this was part of Mr. Torres’s setting you up when he testified about that?
A. I can’t answer for him.
Q. You heard him testify about that, didn’t you?
A. Yes. He wasn’t telling the truth.
Q. Okay. And when he testified that you were one of . the people that Franklin Pratts [sic] put in charge of the whole suitcases — bringing them to the carrousel, that wasn’t true either; right? That’s your testimony?
A. ... I’m not understanding what the question is.
Q. So the statement that he was the one who arranged the job and put people he could trust in charge of the job, you being one of them — that’s not true; right?
A. He also said I was downstairs picking up the bags, and then he also said I was upstairs helping him with the bags.
Q. So that can’t be true can it; right?
A. You can’t be in two places at the same time.
Q. And so the statement that you were one of Frank Pratts’s [sic] trusted people who could handle the suitcases full of drugs — that wasn’t a true statement; right? ....
A. That was not a true statement.
Q. That was not a true statement because you were not one of Frank Pratts’s [sic] trusted people, were you?
A. No. I guess I wasn’t one of his trusted people.
Q. And you weren’t always outside to help -the person pick up the suitcase then. Right? That was another statement of Gerardo Torres. That wasn’t true at all, was it?
A. The only way I could be outside picking up bags was if there was a crew chief that would allow me to get away from my assigned work so I could go upstairs and help somebody pick up bags.

Set 8 related to Torres’s testimony that, to help ensure smooth pickups of the drug suitcases, Pereira would meet co-conspirators picking up the suitcases at the baggage carousel to provide further instructions. JA1094.

Q. Because you didn’t know Gerardo Torres, the fact that he met you, Frank Pratts [sic] ... that never happened either; right?
A. No. It did not happen.
Q. So that’s not correct then. That was another thing that Mr. Torres made up; right?
Defense: Your Honor, questions as to what Mr. Gerardo Torres made up or didn’t make up, it’s like bringing something out.
Court: Overruled.
Q. That’s something else that Gerardo Torres made up and put against you. A. Yes. It’s a good story, but it didn’t happen.

Set 4 related to Torres’s testimony that on one occasion, in furtherance of the conspiracy, Pereira allowed Torres and co-conspirator Camacho inside an AA locker room to exchange a bag of drug money to be smuggled to Puerto Rico. JA 1096-98.

Q. If Gerardo Torres said that you were with Gerardo and Mr. Camacho, once again, that’s another thing he’s making up against you; right? Right?
A. Can I explain that one, sir?
Q. Is it something he’s making up against you?
Court: Is he making that up? .... The question is if Mr. Torres said that you were with him and Mr. Camacho, whether that’s true or not.
A. That wasn’t the question he asked me. But no, that’s not true.
Q. ... [B]ut you’ve never seen Carlos Camacho before until you got to court; right?
A. Correct. I never met Carlos Camacho.
Q. So that’s something he made up; right?
A. You’re answering your own question.
Q. No. I’m asking you what the question is.
Court: Let’s not get into an argument here. The question is [if that’s] something that[ ] Mr. Torres made up.
Defense: But he is not the person to say that Mr. Torres made it up or not. He is not Mr. Torres.
Court: Overruled.... If it’s not true, then it’s something Mr. Torres made up.
A. Correct. It’s a lie.

Set 5 related to Olmo’s testimony that Pereira was part of the conspiracy. JA 1099.

Q. So Mr. Javier Olmo — [you] were also present for his testimony, sir?
A. Yes, I was.
Q. And once again, is he also involved in the same setup as Mr. Gerardo Torres against you?
A. I can’t say what they’re—
Defense: Objection, Your Honor. We’re objecting to the setup. That’s improper. We don’t know what they did, but it’s proper [sic] saying they were set up.
Prosecution: I’m using his own words, Your Honor.
Court: He’s using the witness’s own language. I think the witness understands what he means.
Defense: Your Honor, this is testimony as to Olmo.
Prosecution: I’m asking him.
Court: Yes. He said it about Mr. Torres. Now the question is about Mr. Olmo, whether what Mr. Olmo said was trying to get at you. Do you know that?
A. I don’t personally know that.

Set 6 related to Olmo’s testimony that Prats and Pereira were known as “catchers” among the conspirators because they were the ones who would receive and unload the drugs off the airplanes. JA 1103-04.

Q. ... [W]hen Javier Olmo described you and Frank Pratts [sic] as catchers— do you remember when he testified about that?
A. Yes.
Q. And once again, that was something he made up; right? With regard to you.
A. Yes. He made that up.

Set 7 related to Olmo’s testimony that Pereira was the stand-in for Prats when Prats was absent, in delivering and receiving drugs and payments in furtherance of the conspiracy. JA 1104-05.

Q. And so when Javier Olmo said that you would be the deliverer of large payments in cash when Frank Pratts [sic] wasn’t around,'that’s something he made up; right?
Defense: That’s an improper question.
Court: Overruled.
Q. And Javier Olmo said that you would be the person to deliver large amounts of cash from drugs, that was something he made up about you; right? .... You didn’t do that; right? You didn’t deliver money to anybody who was a member of this drug-trafficking organization.
A. I did not do that.

Finally, set 8 of the prosecutor’s questions related to Olmo’s testimony that Per-eira’s activities in the conspiracy included delivering drug monies, communicating directly with Rodríguez, and once tipping off a co-conspirator about law-enforcement monitoring. of a drug suitcase. JA 1106.

Q. And these are all things that Javier Olmo, if he said, would have had to have been made up.
A. Correct.

. B.

The government argues that “[although defense counsel objected to” some of the questions at issue as “allégedly speculative, [defense] did not argue (as Pereira does on appeal) that the question[s] violated the- general rule proscribing a lawyer from asking a witness whether another witness was lying. Thus, this objection did not preserve Pereira’s argument on appeal.” Appellee Br. 13 n.4 (citation omitted).

We disagree with the government that such objections did not preserve this ground for appeal at least as to question sets 3-8.

With respect to question set 1, as we discuss below in Section D, we do not decide whether the questions were improper (due to the defendant’s having used the setup language in the first instance). Under these circumstances, we need not address whether Pereira preserved an objection. With respect to question set 2, there were no proper objections, thus making the error unpreserved.

In question set 3, the defense objected that ‘Tour Honor, questions as to what Mr. Gerardo Torres made up or didn’t make up, it’s like bringing something out.” JA 1094. The objection focused on “what Mr. Gerardo Torres made up or didn’t make up,” which identified the problem with the prosecutor’s questions. Moreover, the context of earlier objections in question set 1, particularly the objection ‘Tour Honor, this is calling for speculation. The witness is not here. He’s asking for what the. other person thought, what the other person wanted,” JA 1056, provided context that the defendant was objecting in question set 3 based on speculation.

With respect to question sets 4 and 5, the objections were explicit. In question set 4, the defense objected: “But he is not the person to say that Mr. Torres made it up or not. He is not Mr. Torres.” JA 1098. In question set 5, the defense objected: “Objection, Your Honor. We’re objecting to.the setup. That’s improper. We don’t know what they did, but it’s proper [sic] saying they were set up.” JA 1099. It is clear that these objections are on the grounds that Pereira should not be required to speculate as to whether other witnesses are making up testimony or setting him up.

In question set 7, the defense objected “[t]hat’s an improper question.” JA 1104. It is clear from earlier objections and the context that this was in response to a “make up” question.

Finally, the defense did not object during question sets 6 and 8 after counsel had repeatedly objected to. similar questions earlier in the examination. The court “must :.. have realized [the prior objections’] applicability ... as covering the [entire] testimony” on the issue, and the defense undoubtedly felt that “further objection would be futile” at this point. United States v. Elkins, 774 F.2d 530, 536 (1st Cir. 1985). Therefore, having objected repeatedly to “setup” and “made up” questions in these instances during cross-examination, we conclude that the defense counsel sufficiently preserved an objection based on speculation for question sets 3, 4, 5, 6, 7, and 8.

As for the sufficiency of the speculation ground for objection, the very rationale for the were-they-lying-questions rule is that witness “credibility judgments are for the jury, not witnesses, to make.” Thiongo, 344 F.3d at 61. Objections that the questions asked for speculation about other witnesses, or that Pereira “is not the person to say that Mr. Torres made it up or not,” JA 1098, fit precisely within the heart of the rule’s rationale. We agree that such objections suffice because the defense “demonstrate^] ... that the ground for the objection was obvious from the context in which it was made.” Boyd, 54 F.3d at 872; see also Elkins, 774 F.2d at 536 (recognizing that when a court realizes that an objection covers the entire testimony, further objections are unnecessary).

C.

We next consider whether the questions in sets 3-8 were improper. Each of these six sets contains questions that effectively asked Pereira whether he thought Torres or Olmo was lying — seven times in questioning the witness about Torres’s testimony and six times in questioning the witness about Olmo’s testimony (including the follow-up questions posed by the court). The government does not dispute that these questions violated the general rule prohibiting a prosecutor from asking a witness whether another witness was lying, and the government could hardly argue otherwise.

The prosecutor’s improper questions were further exacerbated by judicial intervention that compelled Pereira to answer. For example, with respect to the issue of whether Pereira had ever met co-conspirator Camacho, the court interjected and asked directly: “The question is [if that’s] something that[ ] Mr. Torres made up.” JA 1097. The court went on to further rephrase: “If it’s not true, then it’s something Mr. Torres made up.” JA 1098. In another example, the court expanded the prosecutor’s “setup” questions about Torres to be used in the questions about Olmo. When the defense counsel objected, the court overruled, reasoning that “[y]es[,] [h]e said it about Mr. Torres. Now the question is about Mr. Olmo, whether what Mr. Olmo said was trying to get at you. Do you know that?” JA 1099. Instead of sustaining objections to improper prose-cutorial questioning or issuing curative instructions, judicial intervention here seemed to have reinforced the prosecutorial misconduct.

D.

In response, the government makes two arguments as to why this general rule should be inapplicable here.

First, the government argues that Pereira himself opened the door to these “setup” questions during the cross examination. This may have merit with respect to set 1, where the government asked why Torres would go into Pereira’s Facebook page and obtain his photo, and the defendant answered — without inducement — that the reason was “probably to set me up.” JA 1056. The problem is that with respect to question sets 3 and 4, the government seized upon Pereira’s answers in question set 1, and veered into asking the witness similar questions about other subjects of Torres’s testimony as to which Pereira had not suggested a “setup” motivation.

Moreover, even if we were to agree with the government that “Pereira himself opened the door to the prosecutor’s questions by freely testifying that Torres set. him up,” Appellee Br. 19, as to the questions concerning Torres’s testimony, the government certainly engaged in prosecu-torial misconduct when it followed up during question sets 5, 6, 7, and 8, asking whether the other government cooperating witness (Olmo) also “made up” testimony as a part of a “setup.” With respect to Olmo, the government conceded that the defendant did not introduce any answers on his own that would justify such questions. See Oral Arg. 11:08-11:17 (agreeing that “[t]he defendant didn’t open up that line of questioning as to Olmo.”). We therefore reject the government’s argument that the extension of testimony after set 1 was permissible because Pereira had opened the door.

Second, the government argues that because Pereira and the cooperating government witnesses gave directly contradictory testimony, this “left open only the suggestion that Torres and Olmo were making up stories,” rather than “an interpretation that Torres and Olmo simply spoke out of mistake or hazy recollection.” Appellee Br. 20, 22. Thus, according to the government, because of the clear conflict, it was proper for the prosecution to ask the- defendant whether the government witnesses were lying. The government relies on two state law cases, State v. Hart, 303 Mont. 71, 15 P.3d 917 (2000), and People v. Overlee, 236 A.D.2d 133, 666 N.Y.S.2d 572 (1997), to support its proposed rule that where there exists a direct contradiction in testimony, this justifies asking whether another witness is lying. We decline to follow these cases. Our reasons are several.

The government does not call to our attention any federal cases that hold that a direct conflict in witness testimony renders was-the-witness-lying questions appropriate. Quite the contrary, this court and other circuits have clearly held that such questions are improper in situations where witness testimony did directly conflict. For example, in Sullivan, we held the following exchange to be improper:

Q: So, I take it you would deny that you ever stated to [witness] that you wished you didn’t have so many people involved in the robbery? ...
A: I certainly do, yes.
Q: I take it that, when [witness] testified to that, you would say he was lying? ... I take it you would say that that was a lie, that you never said anything like that.
A: You take that correctly, yes.

Sullivan, 85 F.3d at 749 n.2. Similarly, in United States v. Fernandez, 145 F.3d 59 (1st Cir. 1998), we held the following exchange to be improper:

Q: You showed the agent a roll of money you had in your pocket, didn’t you, sir?
A: No, negative.
Q: So, [witness] who testified yesterday[,] he’s lying?
A: I don’t know why he said that, but I did not show it....
Q: Sir, you did state that that place was full of Customs agents, didn’t you?
A: God, I haven’t said anything like that....
Q: So, [witness] who testified yesterday that you said that is lying, right? ... So [witness] is making all that up, right, sir?
A:- I don’t know what I could say. I didn’t say anything as to that matter.

Id. at 64 n.1 (second alteration in original).

In United States v. Boyd, 54 F.3d 868 (D.C. Cir. 1995), the defendant testified that he never held a bag of cocaine in his possession while two government witnesses testified that he did, which prompted the prosecutor to ask the defendant why the government witnesses would be “making this up.” Id. at 37. In United States v. Harris, 471 F.3d 507 (3d Cir. 2006), “the prosecutor restated various assertions of police witnesses that directly contradicted Harrises] testimony and then asked Harris if it was his testimony that the police witnesses were lying.” Id. at 510. And in United States v. Combs, 379 F.3d 564 (9th Cir. 2004), the government witness testified that the defendant had stated that he manufactured methamphetamine, while the defendant denied making this statement, which prompted the prosecutor to ask the defendant if he thought the government witness was “lying in his testimony.” Id. at 567. In each of these exchanges, there was certainly a direct contradiction between two witnesses, and in each instance, the questioning was held to be improper.

Even where there is a direct conflict between a defendant’s testimony and a government witness’s testimony, asking if one of these witnesses is lying still runs counter to important policies of the rule. One of the policies behind this prohibition is to not force a witness “to choose between conceding the point or branding another witness as a liar.” United States v. Gaines, 170 F.3d 72, 82 (1st Cir. 1999). Such accusatory answers, if required, would put a defendant in a disadvantageous position in front of the jury.

The very structure of the question is designed to pit the testifying witness against every other adverse witness, suggesting to the jury that someone is deliberately deceiving the court.... [T]he were-they-lying questions ... prejudicially force the testifying defendant to accuse or not. Even worse, the defendant’s answer often does not matter because the predomina[nt] purpose of such questions is to make the defendant look bad.

Schmitz, 634 F.3d at 1269. Another policy behind prohibiting such questions is “because they seek an answer beyond the personal knowledge of the witness.” Id. at 1268. A witness would lack personal knowledge of “whether another is intentionally seeking to mislead the tribunal,” Harris, 471 F.3d at 511, regardless of whether his or her testimony is in conflict with the other witness’s. Therefore, where there is a direct conflict in testimony, important policies behind this rule are still implicated.

Finally, restricting the government from asking is-the-witness-lying questions does not unreasonably impair the government’s ability to question a witness fully. We recognize that “it is often necessary on cross-examination to focus a witness on the differences and similarities between his testimony and that of another witness,” and this is proper if the defendant “is not asked to testify as to the veracity of the other witness.” Schmitz, 634 F.3d at 1269 (quoting Harris, 471 F.3d at 512). The objective of highlighting the conflict can be achieved by “[ajsking a witness whether a previous witness who gave conflicting testimony is ‘mistaken!,]’ [to] highlight[ ] the objective conflict without requiring the witness to condemn the prior witness as a purveyor of deliberate falsehood, i.e., a ‘liar.’” United States v. Gaind, 31 F.3d 73, 77 (2d Cir. 1994). For example, in Gaines, when the government witnesses identified the defendant as the drug dealer but the defendant denied these allegations — a direct contradiction— this court approved of cross-examination questions where “[t]he prosecutor ... did not ... ask the witness whether he believed the others had lied. Instead, he asked whether the other witnesses ... were “wrong,’ rather than ‘lying.’ ” 170 F.3d at 81-82.

We conclude that the government’s questions in this case in sets 3-8 were both extensive and improper. In these circumstances, we do not have to consider whether question set 1 was improper or whether question set 2 constituted plain error. “[W]hen there are both preserved and unpreserved errors, cumulative-error analysis should proceed as follows: First, the preserved errors should be considered as a group under harmless-error review. If, cumulatively, they are not harmless, reversal is required.” United States v. Caraway, 534 F.3d 1290, 1302 (10th Cir. 2008). As we now discuss, the preserved errors were not harmless.

III.

“That this [was-the-witness-lying-question] rule was violated by the prosecution is not the end of the analysis. The [next] question is whether the violation of the rule was harmless.” Sullivan, 85 F.3d at 750. “In deciding whether a new trial is required [ ] because [of] prosecutorial misconduct ... [,] we consider the severity of the misconduct, whether it was deliberate or accidental, the likely effect of the curative instruction, and the strength of the evidence against the appellants.” United States v. Cox, 752 F.2d 741, 745 (1st Cir. 1985); see also Sepulveda, 15 F.3d at 1182 (holding that harmless error analysis is a “case-specific inquiry considering, among other things, the centrality of the tainted material, its uniqueness, its prejudicial impact, the uses to which it was put during the trial, [and] the relative strengths of the parties’ cases”).

Here, the repeated and numerous occasions in which the prosecutor engaged in these was-the-witness-lying questions were surely deliberate. So too the prosecutor’s repeated “setup” questions constituted severe misconduct when coupled with judicial intervention that significantly exacerbated the misconduct (as discussed further below). There were no curative instructions for any of the improper questions. Nor was there substantial untainted evidence against Pereira.

In assessing the strength of the evidence, we look at the record excluding the improper questions and the testimony generated by those questions. See, e.g., Fernandez, 145 F.3d at 64-65 (holding that “[m]uch of the case against Fernandez rested on undisputed evidence” not generated by the improper questions, and concluding that “[g]iven the strength of the government’s case, it stretches credulity to believe that the improper ... questions affected the outcome of the trial.”). Excluding the improper questions and the testimony generated by those questions, the case against Pereira was largely dependent precisely on the assessment of Pereira’s credibility versus the credibility of Torres and Olmo. The testimony of Torres and Olmo, moreover, had little self-corroborating substance, and the circumstances presented a basis to infer that they had a reason to lie. The testimony of Torres and Olmo was essential and primary to the government’s case. Beside their testimony, the only other evidence against Per-eira was a piece of Prats’s stationery found at Rodriguez’s house containing Pereira’s first name and phone number and the fact that Pereira took an unusually short trip to Puerto Rico. There was no other evidence that could support a conviction. In short, this was a case in which we cannot conclude with a high degree of confidence that the improper questions and the testimony generated by those questions had no effect on the jury’s assessment of the credibility battle between Pereira and the prosecution witnesses. In the context of such a case, which hinged on the outcome of a swearing contest that would well have been affected by improper questions, it is difficult to see how the improper questions in sets 3-8 could be harmless error under the prevailing test.

Nevertheless, relying on Sullivan, the government recycles the argument that the prosecutor’s questions here only made clear to the jury that the opposing witness testimony was directly contradictory.

In Sullivan, the government primarily relied on testimony from two cooperating witnesses who had participated in a robbery with the defendant to convict Sullivan of armed robbery. 85 F.3d at 746-47. At trial, a secondary government witness testified that the defendant had made a tangential remark about the robbery, which Sullivan denied having said, prompting the prosecutor to ask whether Sullivan thought the witness was lying. Id. at 749 n.2. This court held that the question was improper but harmless, because there were a total of six witnesses who testified against the defendant and the improper question only pertained to a single tangential remark made by a secondary witness, which made the court conclude that “the error was on a minor point.” Id. at 750; see also United States v. Moreland, 622 F.Sd 1147, 1160 (9th Cir. 2010) (holding that two witnesses “were peripheral witnesses because they testified regarding matters of minor importance to the case”). While Sullivan mentioned in passing that it “was obvious” that “there was a contradiction between [the government witness’s] testimony and” the defense testimony, 85 F.3d at 750, Sullivan cannot be read to suggest that in every case the existence of directly contradictory testimony renders the questions harmless.

The government also relied on two other cases, Fernandez, 145 F.3d at 64, and United States v. Robinson, 473 F.3d 387, 396 (1st Cir. 2007), which contained improper was-the-witness-lying questions that were reviewed under a plain error standard. In plain error review, the standard for finding an error harmless is less demanding, at least in the sense that the defendant bears the burden of showing prejudice. United States v. Plano, 507 U.S. 725, 734, 113 S.Ct. 1770, 123 L.Ed.2d 508 (1993) (holding that the “important difference” between plain error review and harmless error review is that, in the former, “[i]t is the defendant rather than the Government who bears the burden of persuasion with respect to prejudice”); see also United States v.. Gandia-Maysonet, 227 F.3d 1, 5 (1st Cir. 2000) (holding that the “main practical difference between the two standards is that plain error requires not only an error affecting substantial rights but also a finding by the reviewing court that the error has seriously affect[ed] the fairness, integrity, or public reputation of judicial proceedings” (alteration in original) (quotation marks omitted)).

Like Sullivan, Fernandez is clearly distinguishable because the court emphasized the other strong government evidence linking the defendant to his crimes. Moreover, the questions were limited in number and scope, and only pertained to tangential, corroborated testimony. 145 F.3d at 61-64. Robinson also held that such questioning was harmless. 473 F.3d at 395-96. The Robinson court discussed the directly conflicting nature of the testimony in finding an absence of prejudice from these questions. Id. at 395-96. However, like Sullivan, Robinson is distinguishable because the government had other strong evidence linking the defendant to the crime. Furthermore, there were only two improper questions, they both pertained to tangential testimony, and an objection was sustained as to one of the two. See id. at 391— 92, 395-96.

DeSimone, not relied on by the government, is also distinguishable. There, the questions concerning whether prior witness testimony was “false” or “untruthful” were held to be in error but found to be harmless. 699 F.3d at 128. While the court relied on the rationale that “[t]here were obvious inconsistencies between DeSi-mone’s testimony and that of other witnesses which were apparent to the jury” for finding harmless error, id. the untainted evidence against DeSimone was substantial, including evidence of flight to avoid prosecution, id. at 118-123. In fact, the DeSimone court cited prior case authority recognizing that “the greater the weight of the other evidence against the defendant, the less likely it is that a given error swayed the jury.” United States v. Cudlitz, 72 F.3d 992, 999 (1st Cir. 1996).

Most important from a harmless error perspective, in none of these cases (Sullivan, Fernandez, Robinson, and DeSimone) was the improper questioning nearly as extensive as it was here, and in none of these cases did the district court participate in the improper questioning.

This case is far more similar to United States v. Geston, 299 F.3d 1130 (9th Cir. 2002), where even applying a plain error review, the Ninth Circuit held that permitting the prosecutor to ask defense witnesses whether they thought the government witnesses were lying was an error that required reversal. In Geston, the case rested on conflicting testimony, in which four eyewitnesses testified for the government and two for the defense. Id. at 1135-36. The prosecutor asked the two defense witnesses whether they thought the government witnesses were lying. On appeal, the court held that “it is reversible error for a witness to testify over objection whether a previous witness was telling the truth.” Id. at 1136. The court went on to explain that “[tjhis case was a close one.... [Defendant’s] fate hinged on resolution of the conflicting testimony presented by the parties.... In a case where witness credibility was paramount, it was plain error for the court to allow the prosecutor to persist in asking witnesses to make improper comments upon the testimony of other witnesses.” M. at 1136-37 (citation omitted).

As we have discussed, witness credibility was also paramount in this trial. In his closing argument, the prosecutor emphasized the improper questioning by referring to the “pretty elaborate setup,” and telling the jury that if it “believe[s] that [setup], then [it] can’t believe Javier Olmo, and ... can’t believe Gerardo Torres. It’s that simple.” Add. 33-34. The government itself recognized the core credibility contest on which the case against Pereira hinged, and the important role that the “setup” questions played.

Finally, and perhaps crucially, here, as in Combs, the “prejudicial effect of the improper questioning was compounded when the district judge placed upon it [his] imprimatur.” 379 F.3d at 573. In Combs, the district court “twice ... instructed [the defendant] to answer the prosecution’s question about the truthfulness of [the government witness’s] trial testimony.” Id. at 573-74. Here, the district court was even more actively involved than in Combs. For example, in question sets 4 and 5, the court directly asked Pereira— over objection — the improper questions that the prosecutor had been asking Per-eira. Thus, the error of the improper prosecution questions was further exacerbated by judicial intervention.

The ultimate test for harmless error is that “[a] new trial is unwarranted so long as we are able to conclude -with a high degree of confidence that the alleged pros-ecutorial misconduct did not affect the outcome of the trial.” Smith, 982 F.2d at 684. Given the severity of the misconduct, the dearth of other evidence, the repeated questions by the government, the evidently deliberate nature of this conduct, the absence of a curative instruction, and the participation of the district court in these questions, we are unable to conclude with a high degree of confidence that the prose-cutorial misconduct here did not affect the outcome of the trial. We therefore hold that a new trial is warranted.

IV.

In light of our disposition, we need not address Pereira’s additional objections on" appeal.

CONVICTION VACATED AND REMANDED FOR NEW TRIAL.

      . The Ninth Circuit in fact holds that asking such questions constitutes plain error. See, e.g., Alcantara-Castillo, 788 F.3d at 1192, 1195 (holding that questioning the defendant about whether a government witness was "making that up,” "lying in his testimony,” or "inventing stories about you” constituted plain error); United States v. Combs, 379 F.3d 564, 572 (9th Cir. 2004) (holding that forcing a defendant to call a government witness a liar is plain error).

      . Fed. R. Evid. 608(a) provides that “[a] witness’s credibility may be attacked or supported by testimony about the witness's reputation for having a character for truthfulness or untruthfulness, or by testimony in the form of an opinion about that character.” Courts have held that although this rule "permits testimony concerning a witness's general character or reputation for truthfulness, it prohibits any testimony as to a witness’s truthfulness on a particular occasion.” United States v. Charley, 189 F.3d 1251, 1267 n.21 (10th Cir. 1999) (quotation marks omitted); see also United States v. Pandozzi, 878 F.2d 1526, 1532 (1st Cir. 1989) (explaining that Rule 608(a) bars asking a witness to evaluate another witness’s veracity).

      . At the same time, the DeSimone court held that “[t]he government correctly concedes that [t]he instances of 'untruthful testimony’ ... and 'giving false testimony’ ... are somewhat closer to the line. Indeed, they went over the line.” 699 F.3d at 128 (alterations in original) (quotation marks omitted).

      . Pereira contends that this judicial intervention, along with other actions of the district court, violated his due process right to a fair trial. See Appellant Br. 36-43. Given the conclusions we reach, we need not address this argument. The district court’s conduct in questioning Pereira is, however, a relevant consideration in the analysis of the issues that we do reach.

      . Some cases have held or suggested that such questions may be permissible "if a defendant opened the door by testifying on direct that another witness was lying.” United States v. Harris, 471 F.3d 507, 512 (3d Cir. 2006); Boyd, 54 F.3d at 871, n.* ("Had [defendant] testified on his own that the [witnesses] were lying, such questioning might be proper.”).

      . Two improper questions were posed in Sullivan, 85 F.3d at 749 n.2, four in Fernandez, 145 F.3d at 64 & n.1, two in Robinson, 473 F.3d at 395, and two in DeSimone, Brief for Appellant at 57-58, United States v. DeSimone, 699 F.3d 113 (1st Cir. 2012) (No. 11-1996), 2012 WL 1572561, at *57-58.