### In the 

# United States Court of Appeals For the Seventh Circuit

____________________ No. 18-2604

U NITED S TATES OF A MERICA , Plaintiff-Appellee ,

v.

M ICHAEL C LARK , Defendant-Appellant

.

____________________ Appeal from the United States District Court for the Western District of Wisconsin. No. 3:17-cr-53-JDP-1 — James D. Peterson , Judge

.

____________________
A RGUED M AY 22, 2019

— D ECIDED A UGUST 15, 2019

____________________

Before B AUER , H AMILTON , and S CUDDER , Circuit Judges

. H AMILTON , Circuit Judge . Defendant-appellant MichaelClark was convicted of possessing a mixture containing fentanyl in violation of 21 U.S.C. § 841(a)(1). Clark had been found in a hotel room with more than 80 grams of a mixture of heroin and fentanyl, a digital scale, and cellophane bags.He does not appeal any aspect of his jury trial, but he challenges the denial of his motion for a Franks hearing challenging the issuance of the search warrant for the hotel room. He2 No. 18-2604

also challenges the denial of his motion to suppress without an evidentiary hearing. And he challenges two aspects of his sentence: the guideline treatmen t of his conviction for drug distribution that occurred in Illinois seven months after his Wisconsin arrest and one conditio n of supervised release. We vacate Clark’s conviction and remand for an evidentiary hearing on his Franks challenge. We a ffi rm on the denial of his motion to suppress without a hearing. We also a ffi rm on the guideline issue and determine that the supervised release challenge was waived. We address in Part I the need for a Franks hearing and in Part II the need for an evidentiary hearing on the motion to suppress. We address the sentencing issues in Part III.

I. The Need for a Franks Hearing The Fourth Amendment’s strong preference for the use of search warrants calls for probab le cause determinations by a “neutral and detached magistrate” as opposed to “o ffi cer[s] engaged in the often competitive enterprise of ferreting out crime.” Johnson v. United States , 333 U.S. 10, 14 (1948). The application for a warrant “must pr ovide the magistrate with a substantial basis for determinin g the existence of probable cause.” Illinois v. Gates , 462 U.S. 213, 239 (1983).The ability of the neutral and detached magistrate to determine probable cause depends on the accuracy of the information the police submit. “[A] search warrant is not valid if the police obtain it by deliberately or recklessly presenting false, material information,” or by omi tt ing material information from the a ffi davit provided to the issuing judge. United States v. McMurtrey, 704 F.3d 502, 508 (7th Cir. 2013), citing Franks v. Delaware , 438 U.S. 154, 155

 56 (1978). To invalidate a warrant on this basis, a defendant at a so-called FranksNo. 18-2604 3

hearing must prove by a preponderance of the evidence either falsity or recklessness, as well as materiality. McMurtrey, 704 F.3d at 509. Merely to obtain a Franks hearing, however, a defendant does not need to prove the Franks violation. A defendant mustonly make a substantial preliminary showing (1) that the warrant application contained a material falsity or omission that would alter the issuing judge’s probable cause determination, and (2) that the a ffi ant included the material falsity or omi tt ed information intentionally or with a reckless disregard for the truth. United States v. Glover, 755 F.3d 811, 820 (7th Cir. 2014); see also, e.g., United States v. Hancock , 844 F.3d 702, 708 (7th Cir. 2016); United States v. Mullins , 803 F.3d 858, 861–62 (7th Cir. 2015); United States v. Robinson , 546 F.3d 884, 887–88 (7th Cir. 2008). “Proof by a preponderan ce of the evidence is not required until the Franks hearing itself.” Glover, 755 F.3d at 820.Clark asserted in the district court that the police investigator who applied for the search warrant of the hotel room deliberately or recklessly omi tt ed critical information a ff ecting the credibility of the unidenti fi ed informant who told the

o ffi cer about drug distribution at the hotel where Clark wasarrested. The district court denied the motion for an evidentiary hearing on the question. The court agreed that the policehad provided no information about the informant’s credibility. The court found, however, that the police had provided

su ffi cient corroboration for the info rmant’s tip so that the warrant did not depend on the informant’s credibility. That meant the omi tt ed credibility information was not material for Franks purposes. We disagree and fi nd that a hearing is needed. “[W]e review the denial of a Franks hearing for clear4 No. 18-2604

error, but any legal determinations that factored into the ruling are reviewed de novo .” Glover, 755 F.3d at 815; see also Hancock , 844 F.3d at 707

 08.

A. The Warrant Application Investigator Todd Maas is a police o ffi cer in Superior, Wisconsin. He prepared the warrant application and signed the supporting a ffi davit. Maas said that a con fi dential informant contacted him on October 14, 20 15 and told him that earlier that day, he had driven someone to a parking lot adjacent to the Baywalk Inn in Superior to buy heroin from a black male called “Big Mike,” the brother of “Toonchie.” Maas said he and another o ffi cer then performed their own investigations, including surveillance of the parking lot. Maas observed a black male leave the hotel and enter and then exit at least fi ve cars in the hotel parking lot. He also learned that the guest staying in Room 203 was the on ly hotel guest who both had paid in cash and was staying only one night, all behavior that Maas said was typical of drug tra ffi cking, based on his training and experience. Maas also sa id he had spoken to a woman (referred to in this case as th e “mom on a mission”) who said that her daughter was a heroin addict and that she (the mother) had followed a man she suspected of drug-dealing to Room 203.

Maas included all of this information in his a ffi davit, which convinced a state trial judge to issue a search warrant for Room 203. Maas did not include any damaging information about the credibility of his con fi dential informant, who was the only source of information speci fi cally about drug tra ffi cking. The informant was being paid for his services. He also had two pending criminal charges against him, fi fteen prior convictions, and a history of opiate and cocaineNo. 18-2604 5

abuse, and he was hoping to re ceive a reduced sentence in exchange for his cooperation.

B. Materiality

Where an a ffi davit is based primarily on tips from an informant, probable cause can be shown based on the totality of the circumstances. Gates , 462 U.S. at 238; Glover, 755 F.3d at 816. In cases based on informants’ tips, we have identi fi ed fi vefactors of particular relevance: (1) the level of detail the informant provided; (2) the extent to which the informant’s information is based on his or her own fi rst-hand observations;(3) the degree to which police have corroborated the informant’s information; (4) the time elapsed between the events reported and the warrant application; (5) and “whether the informant appeared or testi fi ed before the magistrate.” Glover , 755 F.3d at 816, citing United States v. Johnson , 655 F.3d 594, 600 (7th Cir. 2011). Information omi tt ed from a warrant application is material when its omission a ff ects the probable cause determination. Glover, 755 F.3d at 820. In performing this probable cause inquiry, courts must keep in mind that a search warrant for a home, business, oreven hotel room can authorize highly intrusive and even destructive actions by the police, and that informants, especially in drug cases, can be unreliabl e and motivated by rivalries or revenge. United States v. Lopez , 907 F.3d 472, 478 (7th Cir. 2018), quoting Terry v. Ohio , 392 U.S. 1, 16

 17 (1968) (“What we blandly call ‘ Terry stops’ can be highly intrusive.” They are “not just ‘a “pe tt y indignity,”’ wrote the Supreme Court, but ‘a serious intrusion upon the sa nctity of a person, which may in fl ict great indignity and arouse strong resentment, and it is not to be undertaken lightly’”); United States v. Bell , 585 F.3d 1045, 1050 (7th Cir. 2009) (“For all we know, [the informant]6 No. 18-2604

could have been a rival drug dealer, an angry customer, or had some other beef” with the defendant).

Our cases do not hold that a Franks hearing is requiredevery time some substantial adverse information about an informant’s credibility is omi tt ed from a probable cause a ffi davit. Hancock , 844 F.3d at 709. We have said generally that where a warrant is obtained base d on an informant’s tip, “information about the informant’s credibility or potential bias is crucial.” Glover, 755 F.3d at 816; see, e.g., United States v. Bradford , 905 F.3d 497, 503–04 (7th Cir. 2018). That being said, we also have upheld warrants tainted by police omission of adverse informant credibility information. Our Franks hearing cases show that when police have su ffi ciently corroborated an informant’s tip, the omission of facts pertaining to the informant’s credibility may not be material.

In United States v. Musgraves , for example, the police omitted from the a ffi davit important and damaging credibility information about one info rmant. 831 F.3d 454, 459

 60 (7th Cir. 2016). We a ffi rmed the denial of a Franks hearing because a second a ffi davit included information from a second informant without credibility problems who had provided the police with speci fi c and timely information about the suspect’s drug
tra ffi cking to support the warrant. Id. at 460

 61.

In United States v. Bradford, we also held that the a ffi davit’s omission of facts damaging to an informant’s credibility didnot require suppression of evidence seized with a search warrant for drug and weapons tra ffi cking. 905 F.3d at 503

 05. In Bradford , the application failed to disclose that the informanthad three felony convictions, was on probation, and was being paid for his help. Id. at 502. But his information was fresh, speci fi c, and corroborated by his having carried outNo. 18-2604 7

controlled drug buys from the target and by speci fi c information from another informan t without his credibility problems. Id. at 504

In United States v. Hancock , we a ffi rmed the denial of a Franks hearing in similar circumstances. 844 F.3d at 710. An informant provided fresh, deta iled information about a suspect’s drug sales, but the a ffi davit for the warrant left out information about the informant’s own criminal history and the fact that he was in custody when he provided the information. Id. at 705

 06. We found that the omissions were not materialbecause the warrant application included extensive corroboration of the suspect’s drug tra ffi cking and intimidation of witnesses. That corroboration came from other informants, a search of a cellular telephone sh owing texts referring to drug deals, and from an earlier interview with the suspect himself. The quantity and quality of corroborating information meant that the omi tt ed adverse credibility information about one informant did not require a Franks hearing. Id. at 707

 10. This case is readily distingu ishable. This warrant application did not include any of the substantial adverse information Maas had about the informant’s credibility. The government does not try to justify Maas’s om issions, but it argues that theinformant’s credibility was not material to the warrant application because Maas and his colleague investigated and corroborated the informant’s tip su ffi ciently to provide probable cause independent of that tip. We disagree.

The corroboration in this case was much weaker than in the cases where we upheld warran ts’ validity in the face of credibility omissions. This case is more akin to Glover, wherethe warrant application depended so heavily on the credibility of the informant. Here, th e police had no controlled buys.8 No. 18-2604

They never saw money or drugs change hands. Even the informant did not claim to have seen drugs or money change hands. If his tip did not pan out, he had plenty of deniability. He claimed only that his passe nger had met with “Big Mike”outside his presence to buy heroin. And the “mom on a mission” had no track record of credibility and provided no speci fi cs to support her suspicions of the man she had followed to Room 203. In sum, the foundation for probable cause independent of the credibility of th e informant was so meager in this case that the credibility of the informant was material for Franks purposes.
C. Deliberate or Reckless Omissions?

To obtain a Franks hearing, Clark needed to “o ff er direct evidence of [Maas’s] state of mi nd or circumstantial evidencethat [Maas] had a subjective intent to deceive based on the nature of [his] omissions.” Glover, 755 F.3d at 820. In his report and recommendation to the distri ct court, we must note, the magistrate judge in Clark’s case incorrectly read our decision in Gloverto “mandate that ... court[s] infer recklessness from the fact that an o ffi cer omi tt ed known and substantial adverse information from a search warrant a ffi davit....” That is not
correct. In Glover, we held that “credibility omissions themselves, even in the absence of more direct evidence of the offi cer’s state of mind, provide su ffi cient circumstantial evidence to support a reasonable and thus permissible inference of reckless disregard for the truth.” Id. (emphasis added). In other words, credibility omissions do not require courts to infer recklessness. Such omissions are ma tt ers for a trier of fact to weigh, just as when a witness testi fi es incorrectly or falsely about one or a few ma tt ers, and the trier of fact must weigh the rest of the witness’s testimony.No. 18-2604 9

In this case, the questions ofmateriality and the police affi ant’s state of mind are intertwined. To the extent that corroboration might have avoided the need for a Franks hearing in this case, the reliability of the corroboration all depended, from the issuing judge’s point of view, on the same o ffi cer whose credibility is at issue: Maas omi tt ed all adverse information he had about the credibility of the informant who provided the most speci fi c (but still second-hand) information about drug tra ffi cking. As noted, the omission of so much important information permits (but does not require) an inference that the omissions were deliberate or reckless. If theshowing of probable cause in the warrant application depended on the credibility of th e informant, that permissible inference should be enough to obtain a Franks hearing.The district court’s and government’s rationale for denying a Franks hearing is that Maas’s own observations supply probable cause, independent of the informant. We assume that if Maas’s own observations are credited, they could lead a reasonable judge to fi nd probable cause, though the application would have been muchweaker without the informant’s tip to Maas. The problem is that Maas’s credibility can legitimately be questioned he re based on what could have been deliberate or reckless omissions of information about the credibility of the informant. This is where materiality and intent become intertwined. If the omissions were deliberate or reckless, it would not be unreasonable to take seriousl y the prospect that other portions of the same warrant app lication may have been deliberately or recklessly false. Judges often instruct jurors that if they believe a witness has lied intentionally about a material

ma tt er, they may (but are not required to) discount the10 No. 18-2604

witness’s testimony on other ma tt ers. See United States v. Weinstein , 452 F.2d 704, 713–14 (2d Cir. 1971) (no positive rule of law excludes witness’s testimony entirely based on willful falsehood, but such falsi fi cation presents issue for jury to consider in weighing rest of testimony), quoting Knowles v. People , 15 Mich. 408, 412 (1867); Kevin F. O’Malley, Jay E, Grenig, and William C. Lee, 1A Fed. Jury Prac. & Instr. §§ 15:01

 06 (6th ed. 2019). The same point is at the heartof the Supreme Court’s jurisprudence on impeachment evidence in Brady cases. Brady v. Maryland, 373 U.S. 83 (1963), and its progeny establish thatgovernment-suppressed evidence is material “if there is a reasonable probability that, had the evidence been disclosed, the result of the proceeding would have been di ff erent.’” Kyles v. Whitely, 514 U.S. 419, 433

 34 (1995), quoting United States v. Bagley, 473 U.S. 657, 682 (1985). Strong, non-cumulative evidence that undermines the cred ibility of an important government witness satis fi es that de fi nition. Sims v. Hya tt e , 914 F.3d 1078, 1087 (7th Cir. 2019). The reasonis simple. Evidence indicating that a witness whose testimony “may well be determinative of guilt or innocence” is unreliable might prompt a jury to distrust everything the witness says. Giglio v. United States , 405 U.S. 150, 154 (1972). The sa me logic applies in this context. Maas’s potentially intentional or reckless omissioncompromises his credibility, which determines whether probable cause for the warrant existed or not. To be clear, we are not saying or fi nding here that Maas was in fact deliberately or recklessly deceptive. The issue on appeal is only whether Clark was entitled to a hearing, one where Maas’s credibility could be addressed with evidence from both sides. The inform ant was the only source ofNo. 18-2604 11

information (and again, that wa s only second-hand) who said the person in Room 203 was actua lly dealing drugs. All of the other information in the warrant application indicated grounds for suspicion, but we can assume that Maas had a good reason for including the informant’s more speci fi c information. The complete omission of the available damaging information about the informant’s credibility permits an inference that Maas was not being ho nest and careful with the issuing court. Whether he in factwas honest and careful about the facts is an appropriate subject for the Franks hearing on remand. 1

II. The Timing of the Warrant and Search Defendant Clark was in Room 203 when police executed the warrant. Also in the room were cellophane bags, a digital scale, and approximately 82 grams of a mixture of heroin and fentanyl. The police photograph ed the hotel room during their search. In a photograph of suspected drugs on a nightstand, a digital clock is vi sible, reading 8:15 p.m. If the clock was correct, the search was executed at least 25 minutes before the judge issued the warrant.

1 Maas’s application also did not explain why the informant would know heroin if he saw it. See United States v. Peck , 317 F.3d 754, 756

 57 (7th Cir. 2003) (no probable cause for search warrant where affidavit was based on informant’s report of seeing drugs in defendant’s house, but according to affidavit, informant failed to give details about specific location and amount of drugs, or any explanation as to how informant knew that what she saw were controlled substances). Nor did Maas provide the kind ofdetail about his own training and experience that is needed to justify reliance upon them. See generally, e.g., United States v. Scott , 901 F.3d 842, 845 (7th Cir. 2018) (“Details ... are vital when an officer proposes his own training and experience as the basis of a warrant”).12 No. 18-2604

The police of course are not permi tt ed to rely on a searchwarrant that has not yet been approved by a judge. The district court denied Clark’s motion to suppress without a hearing. The issue here is whether the photograph of the clock was

su ffi cient evidence for Clark to have an evidentiary hearing on his motion to suppress. A defendant who requests a suppression hearing must present “de fi nite, speci fi c, detailed, and nonconjectural facts ... demonstrat[ing] that there is a disputed material issue of fact.” United States v. Rodriguez , 69 F.3d 136, 141 (7th Cir. 1995);

see United States v. Curlin , 638 F.3d 562, 564 (7th Cir. 2011). “Reliance on vague, conclu sory allegations is insu ffi cient.” United States v. Randle , 966 F.2d 1209, 1212 (7th Cir. 1992). In response to Clark’s motionto suppress, the government submi tt ed the “metadata” from the digital camera. Themetadata showed a host of data about each photograph, including the time each was taken. The metadata showed that all of the search photographs were taken between 10:36 and 10:52 p.m., well after the judge issued the search warrant. Clark responded in turn not with an a ffi davit from any witness to the search but with resu lts of Google searches about how to edit metadata for photographs. In light of the metadata, and in the absence of any speci fi c indications that data had been altered, the district court decided that there was no need for a hearing and denied Clark’s motion to suppress.

The situation here is similar to United States v. Woods , 995 F.2d 713 (7th Cir. 1993). 2 In Woods , the police conducted a

2 Another portion of the Woods opinion was abrogated by the Supreme Court’s decision in Bailey v. United States , 516 U.S. 137 (1995), as we noted in United States v. Monroe, 73 F.3d 129, 133 (7th Cir. 1995).No. 18-2604 13

search on February 12th. The problem was that both the warrant and the supporting a ffi davit bore handwri tt en dates of February 14th, though both were also date-stamped February 11th. The defendant moved to suppress, arguing that the search had been executed two days before the warrant was issued. The government responded with an a ffi davit from a prosecutor testifying that the application and warrant wereboth prepared and signed on February 11th and that the February 14th dates were mistakes. Using language associated with civil motions for summary judgment—“disputed issues of material fact” and “genuine factual dispute”—we a ffi rmed the district court’s decision to deny the motion to suppresswithout a hearing. Because the defendant had failed to respond to the government’s explanation, we agreed that he had failed to show a genuine fa ctual dispute and a need for an evidentiary hearing. Id . at 715–16. One might argue that in Woods the government submi tt ed

an a ffi davit to explain the discrepancy, while the government here submi tt ed le tt ers and copies of do cuments, without any

a ffi davits. Both parties here submi tt ed various documents to the district court with this le ss formal approach. But the burden is on the defendant to support his motion to suppress.Missing from this record is an assertion by any witness—defendant Clark or anyone else—to the e ff ect that the search actually occurred at 8:15 p.m. and that the clock was correct. Without such an assertion, whether in an a ffi davit or otherwise (given the less formal procedures being used in the district court), the Google searc h results about how to alter metadata merely invite speculat ion. The district court did not err by denying the motion to suppress, to the extent it was based on the photograph of the clock, without a hearing.14 No. 18-2604

III. Sentencing Issues

A. Relevant Conduct Under the Guidelines Clark also challenges two aspects of his sentence. The fi rst is a Sentencing Guidelines issue concerning the scope of his relevant conduct and criminal history, which are two sides of the same coin here. The U.S. Probation O ffi ce prepared a PreSentence Report for Clark. Pursuant to U.S.S.G. § 2D1.1(a)(5) and (c)(8) of the 2016 Sentencing Guidelines Manual, the PSR calculated Clark’s base o ff ense level as 24 because he possessed between 40 and 160 grams of a substance containing fentanyl. No other adjustments applied, so his total o ff ense level remained 24. The PSR also determined that Clark had 11 criminal history points and was in criminal history categoryV. Three of those 11 points were from a 2017 federal conviction for drug distribution stemming from events that occurred in Illinois after Clark was arrested in this Wisconsin federal case. Clark also received three points for a prior felony drug conviction in Minnesota. Because of the Minnesota conviction, Clark faced a 120-month mandatory minimum pursuant to 21 U.S.C. § 851. (If not for the enhancement, Clark would have had an advisory guideline range of 92 to 115 months.) Both the government and Clark argued for the 120-month mandatory minimum sentence. Th e district court adopted the facts of the PSR and determined that the PSR had calculated correctly Clark’s o ff ense level, criminal history, and guideline range. The court sentenced Clark to 120 months in prison tobe served consecutively to the 71-month sentence he had received in the Illinois case. On appeal, Clark argues that his later drug o ff ense in the Illinois conviction should be treated under the SentencingNo. 18-2604 15

Guidelines as “relevant conduct” for this case rather than as part of his criminal history. That means, he contends, his 120- month sentence in this case sh ould run concurrently with the 71-month sentence he received in Illinois. Clark did not raise this argument in the district co urt. At sentencing, the government asked that Clark’s sentence run consecutively to his Illinois sentence. Clark did not object. He requested only that this sentence run concurrently with any state sentence. The government argues that Clark therefore waived this issue. Waiver is the intentional relinquishment of a known right, whereas forfeiture occurs whena defendant “negligently fails to assert a right in a timely fashion.” United States v. Brodie , 507 F.3d 527, 530 (7th Cir. 2007); see United States v. Olano , 507U.S. 725, 733 (1993). Concurrent sentences would reduce signi fi cantly the time Clark spends in prison. There is no reason for us to draw the inference here that Clark intentionallywaived this argument. “Waiver principles should be construed liberally in favor of the defendant,” and we are hesitant, without more, to construe a defendant’s failure to object to a PSR as an intentional re linquishment of a known right. United States v. Jaimes-Jaimes , 406 F.3d 845, 848

 49 (7th Cir. 2005). This is especially the case where, as here, the defendant had no strategic reason to forgo this sentencing argument. See United States v. Jenkins , 772 F.3d 1092, 1096 (7th Cir. 2014). Plain-error review, however, does not win relief for Clark on this issue. Plain-error review allows reversal where: (1)there was an error; (2) the error was plain; (3) the error affected the substantial rights of the defendant; and (4) the error seriously impacted the fairness, in tegrity, or public reputation of the proceedings. Olano , 507 U.S. at 732

 38; United States v. Duran , 407 F.3d 828, 834 (7th Cir. 2005). Here, we need not16 No. 18-2604

address the third and fourth elements. If any error occurred at all, it was not “plain.” Under § 5G1.3(b) of the Guidelines, where a defendant hasan undischarged term of imprisonment, and where the conduct that led to the undischarged sentence

is relevant conduct to the instant o ff ense of conviction under the provisions of subsections (a)(1), (a)(2), or (a)(3) of § 1B1.3 (Relevant Conduct), the sentence for the instant o ff ense shall be imposed as follows: (1) The court shall adjust the sentence for any period of imprisonment alreadyserved on the undischarged term of imprisonment if the court determines that such period of imprisonment will not be credited to the federal sentence by the Bureau of Prisons; and (2) the sentence for the instant o ff ense shall be imposed to run concurrently to the remainder of the undischarged term of imprisonment.Section 5G1.3(d) further advises that “in any other case involving an undischarged term of imprisonment, the sentence for the instant o ff ense may be imposed to run concurrently,partially concurrently, or consecutively to the prior undischarged term of imprisonment to achieve a reasonable punishment for the instant o ff ense.” So if Clark’s Illinois o ff ense was relevant conduct here, the Guidelines would recommend concurrent sentences. If his Illinois o ff ense was not relevant conduct here, the choice of consecutive or concurrentNo. 18-2604 17

sentences is left to the discretio n of the sentencing judge, and there is no reason to fi nd an abuse of discretion here.As for the scope of relevant conduct, § 1B1.3(a)(1)(A) provides that “relevant conduct” is based on “all acts and omissions commi tt ed, aided, abe tt ed, counseled, commanded, induced, procured, or willfully caused by the defendant.” “Section 1B1.3(a)(2) applies to grouped o ff enses and includes ‘all acts and omissions described in subdivisions 1(A) and 1(B) that were part of the same course of conduct or common scheme or plan as the o ff ense of conviction.’” United States v. Schrode , 839 F.3d 545, 551 (7th Cir. 2016), quoting U.S.S.G. § 1B1.3(a)(2). “In assessing whether o ff enses are part of the same courseof conduct, we focus on whether the government has demonstrated a signi fi cant similarity, regularity, and temporal proximity.” United States v. Baines , 777 F.3d 959, 963 (7th Cir. 2015) (internal citations omi tt ed). In considering whether an o ff ense is relevant within the meanin g of § 1B1.3, our court has emphasized several factors that should guide courts’ analysis. “Su ffi cient factual overlap exists where the past and present

o ff enses involve the same victims, stem from the same underlying conduct, or are in fact similar o ff enses.” United States v. Orozco-Sanchez , 814 F.3d 844, 850 (7th Cir. 2016); see also United States v. Sumner , 325 F.3d 884, 889 (7th Cir. 2003) (in deciding relevant conduct in drug cases, courts look for “a strong relationship between the uncharged conduct and the convicted o ff ense, focusing on whether the government has demonstrated a signi fi cant similarity, regularity, and temporal proximity”), quoting United States v. Acosta , 85 F.3d 275, 279 (7th Cir. 1996). The relevant conduct issue is similar to the issue in calculating criminal history under U.S.S.G. § 4A1.218 No. 18-2604

(de fi ning “prior sentence”), where two similar prior convictions separated by an intervening arrest are counted separately. E.g., United States v. Morgan , 354 F.3d 621, 623 (7th Cir. 2003); United States v. Bradley, 218 F.3d 670, 673 (7th Cir. 2000). The district court did not plainl y err in not treating Clark’s later o ff ense in Illinois as relevant conduct for his Wisconsin conviction. To support his argumen t, Clark points to facts set forth in his Wisconsin PSR. The PSR explained that Clark traveled to Chicago to obtain the drugs that he would then sell in Wisconsin. This fact, Clark assert s, establishes that his drugactivities in both states were part of the same course of conduct, his fentanyl-tra ffi cking enterprise.Under our precedents, this argument faces obvious “temporal proximity” and “similarity ” problems. First, Clark was arrested in Wisconsin seven months before he was arrested for selling a fentanyl mixture in Illinois. Further, the o ff enses were dissimilar. In Wisconsin, Clark possessed more than 80 grams of fentanyl, most of whic h was packaged in retail packages of 0.5 grams. In Illinois, by contrast, he was arrested for selling a con fi dential informant more than 65.2 grams of fentanyl. And even if the o ff enses had been more similar, “the fact that a defendant commits a certain type of o ff ense on multiple occasions does not inevit ably mean that each separate

o ff ense is part of the same course of conduct.” Schrode , 839 F.3d at 552. There is not enough here to have required the district court to have found such strong connections between these two drug o ff enses, especially without an objection by the defense to that e ff ect. The o ff enses involved di ff erent buyers, in di ff erent cities, in di ff erent types of quantities, months apart, and with an intervenin g arrest for the Wisconsin offense.No. 18-2604 19

“An error is ‘plain’ if the law at the time of appellate review shows clearly that it was an error.” United States v. Pierson , 925 F.3d 913, 919 (7th Cir. 2019), citing Henderson v. United States , 568 U.S. 266, 279 (2013). Clark cannot establish with precedent or otherwise that the district court should have acted sua sponte to treat his Illinois o ff ense as conduct relevant to his Wisconsin charge. Even if there might have been an error, it was not plain error to run Clark’s two federal sentences consecutively.

B. Supervised Release Condition Finally, the district court imposed a supervised release condition that Clark “Not meet, communicate or spend time with any persons known by defendant to be a member of or

a ffi liate of any known street gang.” On appeal, Clark argues that the term “a ffi liate” is unconstitutionally vague. He did not object to this condition at sentencing. In at least scores of appeals over the past fi ve years, in the wake of United States v. Siegel , 753 F.3d 705 (7th Cir. 2014), United States v. Thompson , 777 F.3d 368 (7th Cir. 2015), and United States v. Kappes , 782 F.3d 828 (7th Cir. 2015), this court has wrestled with how best to handle appellate challenges tosupervised release conditions that were not raised in the district court. Our recent opinion in United States v. Flores , 929 F.3d 443 (7th Cir. 2019), should bring some order to our caselaw in this niche of waiver law, particularly since it was circulated to the entire court under Circuit Rule 40(e), and no judge voted to hear the case en banc. Special considerations apply to our handling of supervised release conditions both because they are usually the leas t salient concern at the time of sentencing and, more important, because a defendant may challenge them in the district court at any time. See Flores , 92920 No. 18-2604

F.3d at 451, citing 18 U.S.C. § 3583(e)(2); see also United States v. Lewis , 823 F.3d 1075, 1083 (7th Cir. 2016) (defendant waived challenge to supervised release condition: “sentencing in the district court is the main event”).

This case meets the standards of waiver set forth in Flores : Clark had prior notice of the proposed conditions, including the “a ffi liate” condition. He had a meaningful opportunity to object, and his lawyer told the judge that the proposed conditions were acceptable. Clark even raised other objections tothe PSR prior to sentencing but did not challenge this condition, which signals an intentional decision not to object. See Flores , 929 F.3d at 449.

We REVERSE the district court’s denial of Clark’s motion for a Franks hearing without an evidentiary hearing. We VACATE the district court’s judgment and REMAND for a Franks hearing and appropriate action based on the outcome of that hearing, either granting Clark’s motion to suppress or,if his motion is denied, reinstating the convictions and sentence. If the judgment is reinstated, the denial of Clark’s motion to suppress and the dist rict court’s sentence are AFFIRMED.No. 18-2604 21

S CUDDER , Circuit Judge , dissenting in part. The panel opinion is well done, and I join all pa rts of it except the conclusion that the district court should have granted Michael Clark’s motion for a Franks hearing. In my view, Investigator ToddMaas’s affidavit supporting the search warrant, while omitting facts damaging to the confidential informant’s credibility—facts that unquestionably should have been included—adequately corroborated the information supplied by the informant. The district judge re ached this precise conclusion, and under the deferential standa rd that guides our review on appeal, we should affirm. There was no clear error here.

I The majority’s opinion correctly articulates the standard for obtaining a Franks hearing: a defendant must make a substantial preliminary showing that an officer intentionally or recklessly omitted information from a search warrant affidavit and the omissions were material to the probable cause determination. See United States v. Glover, 755 F.3d 811, 820 (7thCir. 2014). The majority also rightly observes that the omission of adverse information about an informant’s credibility does not automatically warrant a hearing. See United States v. Hancock , 844 F.3d 702, 709 (7th Cir. 2016). Instead the proper question is whether the affidavit would have established probable cause if the omitted information had been included. See id. at 708. To make this determination, we consider the totality of the circumstances, including “the extent to which the police have corroborated the informant’s statements.” United States v. Sutton , 742 F.3d 770, 773 (7th Cir. 2014). All agree that Investigator Maas failed to disclose critical facts about the informant’s ba ckground. In my judgment, though, the warrant applicatio n had sufficient corroboration22 No. 18-2604

to overcome this omission an d establish the requisite probable cause to search hotel room 203 at the Baywalk Inn. Maas took care to include three ke y pieces of corroborating evidence in his affidavit:

 In response to the informant’s tip about possible drugdealing at the Baywalk Inn, Investigator Maas surveilled the hotel and observed a black male exit the hotel and quickly enter and exit at least five cars. Drawing on his experience as a narcotics investigator,Maas characterized this conduct as “textbook behavior to dealing narcotics.”

 Maas discovered that only two of the hotel’s 25 rooms had been rented with cash, with only one of the two— room 203—being rented for one night, which Maasexplained was consistent with drug trafficking because “drug dealers usually pa y in cash and only stay one or two nights so to throw off police.”

 Maas also reported that, upon arriving at the hotel, he had a conversation with a woman he identified by name in the warrant application, who said her 20- year-old daughter was addicted to heroin. The woman added that, before the officer arrived, she was “also watching the black male who [was] suspected to be dealing” and she followed him to room 203.The majority’s analysis discounts this information, reasoning that Investigator Maas’s om ission of material facts about the informant’s background compromised his credibility on all other portions of the warrant applicatio n. Put another way,if Maas omitted critical information about the informant’s reliability, nothing else he included in his affidavit deserved toNo. 18-2604 23

be credited as part of the probable cause analysis. But our case law does notrequire such broad discounting and distrust. See, e.g ., United States v. Bradford , 905 F.3d 497, 503–05. The district court was not required to view as worthless the entirety of the corroborating information provided by Maas. To be sure, a court faced with a reckless or intentional omission of material informat ion may consider whether (and to what extent) the omission bears on the officer’s credibility as part of its probable cause an alysis. But I cannot say that thedistrict court clearly erred, in light of other corroborating evidence, by choosing to credit Maas’s affidavit despite hisomission. So I would affirm the court’s denial of Clark’s motion for a Franks hearing.

II

A final observation seems worthwhile. When this case entered federal court, a magistrate judge reviewed the statecourt warrant application and note d that it, like many others prepared by law enforcement officers in Wisconsin, omitted information about the confidenti al informant’s criminal history. The panel’s opinion, aligned with our precedent, reinforces that this information is essential to a proper probable cause analysis under the Fourth Amendment. See, e.g ., United States v. Musgraves , 831 F.3d 454, 460 (7th Cir. 2016). Given the frequency with which search warrants sought and executed at the state level result in fe deral prosecutions, Wisconsin law enforcement would do well to revisit its warrant applicationpractices. Omitting information about an informant’s credibility creates real yet avoidable peril. Today’s decision proves the point.