United States v. Iley, 914 F.3d 1274 (2019)

Feb. 4, 2019 · United States Court of Appeals for the Tenth Circuit · No. 17-1269
914 F.3d 1274

UNITED STATES of America, Plaintiff-Appellee,
v.
Donald ILEY, Defendant-Appellant.

No. 17-1269

United States Court of Appeals, Tenth Circuit.

FILED February 4, 2019

Josh Lee, Assistant Federal Public Defender (Virginia L. Grady, Federal Public Defender, with him on the briefs), Office of the Federal Public Defender, Denver, Colorado, for Defendant-Appellant.

Karl L. Schock, Assistant United States Attorney (Robert C. Troyer, United States Attorney, with him on the brief), Office of the United States Attorney, Denver, Colorado, for Plaintiff-Appellee.

Before LUCERO, HARTZ, and HOLMES, Circuit Judges.

HOLMES, Circuit Judge.

For crimes of fraud and deceit, § 2B1.1(b)(9)(C) of the U.S. Sentencing Guidelines Manual ("U.S.S.G." or "Guidelines") provides for a two-level sentencing enhancement if the defendant's offense conduct violated "any prior, specific judicial or administrative order." After investigating complaints regarding the tax-preparation services of the defendant, Donald *1276Iley, the Colorado Board of Accountancy (the "Board") issued an administrative order-called an "Agreement and Final Agency Order" (the "Order"), R., Vol. I, at 78 (Agreement and Final Agency Order, dated Jan. 29, 2010)-in which Mr. Iley admitted to engaging in professionally negligent conduct and agreed to accept certain disciplinary sanctions, including a $10,000 fine and a five-year probationary period. Among the acts for which the Board disciplined Mr. Iley was taking a client's money ostensibly to pay the client's payroll taxes but then failing to promptly and properly pay those funds to the Internal Revenue Service ("IRS"). During his probationary period, Mr. Iley was required to open his practice to monitoring by a third-party accountant, to complete eighty hours of continuing professional education within two years of the Order's effective date, and to submit quarterly reports to the Board in which Mr. Iley was obliged to attest to his continued compliance with the Order's terms.

However, while serving the Order's probationary term, Mr. Iley executed a fraudulent scheme in which he fleeced his clients of more than $11 million. As part of this scheme, Mr. Iley fraudulently misrepresented to his clients that he was taking their funds to pay outstanding payroll taxes to the IRS but, instead, Mr. Iley used those funds for personal purposes. After this fraud was discovered, Mr. Iley pleaded guilty to wire fraud and aiding in the preparation of a false tax return. At sentencing, the district court enhanced Mr. Iley's sentence under § 2B1.1(b)(9)(C). The question before us is whether the court erred in doing so. We hold that, under the particular circumstances of this case, the court did not err. Accordingly, exercising jurisdiction under 28 U.S.C. § 1291 and 18 U.S.C. § 3742(a), we affirm .

I

Donald Iley was an accountant. Until 2015, he was licensed by the Board and owned and operated an accounting firm, Iley & Associates, Inc. Among other services, Mr. Iley calculated clients' payroll taxes, prepared the necessary tax forms, collected money from clients to pay these taxes, and then sent the money and the accompanying forms to the IRS.

Not all of Mr. Iley's clients were satisfied with his services. After receiving multiple complaints about his tax-preparation practices, the Board launched an investigation. Mr. Iley had notice of the investigation, and he responded to the allegations made against him. After conducting meetings on the matter, the Board "found reasonable grounds to refer [Mr. Iley and his business] to [a] hearing for license law violations." R., Vol. I, at 79. However, in 2010, Mr. Iley and the Board ultimately reached an agreement to resolve the matter. Their agreement was memorialized in the aforementioned Order.

In that Order, Mr. Iley admitted to certain acts of professional negligence, gave up his right to a hearing regarding the complaints, and agreed to the Board's imposition of certain discipline. Among other things, Mr. Iley admitted in the Order that he took a client's money ostensibly to pay that client's payroll taxes to the IRS but "failed to properly and promptly remit payment in full to the IRS." Id. at 88. As for the discipline, the Board sanctioned Mr. Iley by requiring him to pay a fine of $10,000 and to submit to a five-year period of probation. During this probationary period, Mr. Iley was obliged to open his practice to monitoring by a third-party accountant to "improve the quality and accuracy of [his] tax services and to determine whether [Mr. Iley] meets the generally accepted professional standards for tax services," including adherence to the *1277Board's ethical rules. Id. at 93. Mr. Iley also was required to complete eighty hours of continuing professional education within two years of the Order's effective date. And, lastly, Mr. Iley was required to submit quarterly reports to the Board attesting to his "compliance with this Order." Id. at 95. The Order expressly warned Mr. Iley that "[a]ny violation of this Order may result in grounds for discipline." Id. at 98.

However, for a year before the Board issued the Order and for approximately five years afterwards, Mr. Iley was engaged in a fraudulent scheme to steal money from his clients. As part of this scheme, Mr. Iley would prepare an accurate form reflecting the payroll taxes a client owed, submit the form for the client's approval, and then withdraw money from the client's accounts under the guise of paying the tax. But Mr. Iley would not send the money to the IRS; instead, he would keep the money for his own personal purposes-including making "payments on his mortgage and his wife's credit card bill." Id. at 7 (Indictment, filed Aug. 24, 2016). To complete the scheme, Mr. Iley would send the IRS a phony form, wrongly showing that the client owed no payroll taxes. There is no indication in the record that the Board was aware of the fraudulent nature of Mr. Iley's misdeeds when it issued the Order in 2010.

As authorized by the Order, Mr. Iley requested early termination of the practice monitoring in 2013. As support for his request, Mr. Iley represented to the Board that he had "learned a great deal from this process, including" the need for "absolute candor with clients." Id. at 25 n.3 (Plea Agreement, filed Apr. 18, 2017). But his actions revealed that Mr. Iley was not being truthful with the Board. Yet, oblivious to Mr. Iley's ongoing fraud, the Board granted Mr. Iley's request. However, the Board later became aware that Mr. Iley (among other things) was still "failing to remit taxes on behalf of clients to the United States Treasury," and it suspended his license in December 2015 and "permanently revoked" it in August 2016. Id. , Vol. II, ¶ 36 (Presentence Investigation Report ("PSR"), filed July 7, 2017).

In late 2015, with some of Mr. Iley's clients now wise to his fraudulent conduct and law enforcement directing their investigative resources at him, Mr. Iley ended his fraudulent scheme. All told, Mr. Iley defrauded his clients of more than $11 million. More than 140 of his clients were identified as victims of the scheme. Many of them ended up owing the IRS interest and penalties because Mr. Iley failed to honor his promises to forward their funds to the IRS to pay their payroll-tax liabilities. And some of his clients were small businesses that were "ruin[ed]" "financially" by his fraudulent scheme. Id. , Vol. V, at 75 (Tr. of Sentencing Hr'g, dated July 13, 2017).

In August 2016, a federal grand jury returned an indictment against Mr. Iley charging him with twelve counts of wire fraud, 18 U.S.C. § 1343, two counts of mail fraud, 18 U.S.C. § 1341, and eighteen counts of aiding in the preparation of false tax returns, 26 U.S.C. § 7206(2). Some months later, Mr. Iley pleaded guilty to one count of wire fraud and one count of aiding in the preparation of a false tax return, in exchange for the government agreeing, inter alia , to dismiss the remaining charges.

The U.S. Probation Office prepared a PSR and computed Mr. Iley's advisory Guidelines sentencing range as ninety-seven to 121 months' imprisonment.1 The PSR

*1278arrived at that range by using a total adjusted offense level of thirty, which included a two-level enhancement under § 2B1.1(b)(9)(C) for Mr. Iley's alleged violation of the Order. Without this "Prior Order" enhancement,2 Mr. Iley would have faced an advisory Guidelines sentencing range of seventy-eight to ninety-seven months' imprisonment.

Mr. Iley objected to the PSR's application of the § 2B1.1(b)(9)(C) enhancement. As he saw it, his fraud conviction was unrelated to the conduct for which the Order had punished him-namely, professional negligence. Thus, as Mr. Iley reasoned, his later fraud did not violate the Order, meaning that § 2B1.1(b)(9)(C) did not apply.

The Probation Office saw things differently. It noted that the Order put Mr. Iley on probation and part of that probation entailed "not engaging in more fraudulent activity." R., Vol. II, at 226 (Addendum to the PSR, dated July 7, 2017). Yet, as the Probation Office explained, Mr. Iley "continued his fraudulent activity." Id. And so the Probation Office reasoned that Mr. Iley had violated the Order and was thus eligible for the § 2B1.1(b)(9)(C) enhancement.

At sentencing, the district court agreed with the Probation Office. It read the Order as telling "Mr. Iley that he needed to stop engaging in.... further fraudulent activity." Id. , Vol. V, at 49-50. The court stated that, despite that warning, Mr. Iley was "actively defrauding" his clients while on probation and thereby violating the Order. Id. at 49. For that reason, the court found that the § 2B1.1(b)(9)(C) enhancement applied to Mr. Iley.

Mr. Iley now appeals, challenging the district court's imposition of the two-level enhancement under § 2B1.1(b)(9)(C).

II

The overarching question of whether a district court correctly computed a defendant's Guidelines sentencing range-and, more specifically, whether it correctly imposed a particular Guidelines enhancement-is a question of procedural reasonableness. See, e.g. , United States v. Huckins , 529 F.3d 1312, 1317 (10th Cir. 2008) (noting that "[p]rocedural reasonableness addresses [inter alia ] whether the district court incorrectly calculated ... the Guidelines sentence"); accord United States v. Martinez-Barragan , 545 F.3d 894, 898 (10th Cir. 2008). However, in assessing whether the district court's computation is correct "we review legal questions regarding the application of the Sentencing Guidelines de novo," and "a district court's factual findings are reviewed only for clear error, giving due deference to the district court's application of the Guidelines to the facts."

*1279United States v. Pentrack , 428 F.3d 986, 989 (10th Cir. 2005) ; see also United States v. Kristl , 437 F.3d 1050, 1054 (10th Cir. 2006) (per curiam) ("We note that this new standard of review-that of 'reasonableness'-does not displace the oft-cited principle that in considering the district court's application of the Guidelines, we review factual findings for clear error and legal determinations de novo.").

We do not appear to have addressed in direct and express terms whether we should assess de novo whether a particular "prior, specific judicial or administrative order, injunction, decree, or process" provides a sufficient basis for the imposition of the Prior Order enhancement.3 U.S.S.G. § 2B1.1(b)(9)(C). And, as it turns out, we need not definitively resolve this standard-of-review question here. That is because the parties present no genuine controversy regarding it. See, e.g. , People for the Ethical Treatment of Property Owners v. U.S. Fish and Wildlife Serv. , 852 F.3d 990, 1008 (10th Cir. 2017) ("[I]f it is not necessary to decide more, it is necessary not to decide more." (alteration in original) (quoting PDK Labs. Inc. v. DEA , 362 F.3d 786, 799 (D.C. Cir. 2004) (Roberts, J., concurring in part and concurring in the judgment) ) ), cert. denied , --- U.S. ----, 138 S. Ct. 649, 199 L.Ed.2d 586 (2018) ; Valley Forge Ins. Co. v. Health Care Mgmt. Partners, Ltd. , 616 F.3d 1086, 1094 (10th Cir. 2010) ("Judicial restraint, after all, usually means answering only the questions we must, not those we can."). Specifically, the parties agree that de novo review governs this question. Compare Aplt.'s Opening Br. at 8 (asserting, without citation to controlling Tenth Circuit authority, that "[d]e novo review also governs the district court's interpretation of the administrative order that Mr. Iley allegedly violated"), with Aplee.'s Resp. Br. at 7 (adopting the de novo approach of the Fifth Circuit).

*1280Thus, we are content to apply de novo review in assessing whether the Order provides a sufficient basis for the imposition of the Prior Order enhancement.

III

This case turns on whether Mr. Iley's fraudulent conduct violated the Order.4 Mr. Iley claims that it did not for two reasons. First, in his view, § 2B1.1(b)(9)(C) applies only when a defendant does something that an "agency had expressly forbidden him from [doing]." Aplt.'s Opening Br. at 7. And because the Order did not expressly enjoin Mr. Iley from committing the same or similar fraudulent conduct for which he ultimately was convicted, Mr. Iley contends that he did not violate the Order. See id. at 6 ("[T]he administrative order clearly delineates the conditions of Mr. Iley's probation, and none of those conditions includes an order not to commit fraud."). Second, Mr. Iley argues that the Order punished him for negligence, not fraud. Hence, Mr. Iley reasons that his fraudulent conduct did not violate the Order because negligence and fraud are different. For either or both reasons, he contends that the district court erred in applying the § 2B1.1(b)(9)(C) enhancement.5

The government disagrees. It says that Mr. Iley's first argument "elevates form over substance." Aplee.'s Resp. Br. at 11. In the government's view, "[a]lthough the Order did not explicitly enjoin [Mr.] Iley from" committing the fraudulent conduct underlying his conviction, "that was the unmistakable implication of the Order." Id. at 10. Thus, the government reasons that, by engaging in fraudulent conduct while the Order was in effect, Mr. Iley violated *1281the Order. As for Mr. Iley's second argument, the government asserts that it is irrelevant that the Order disciplined Mr. Iley for negligent conduct, whereas he was subsequently convicted of fraudulent acts, because "by punishing even negligent conduct, the Order necessarily prohibited [Mr.] Iley from engaging in the same conduct fraudulently as well." Id. at 14. Thus, the government argues that the district court properly applied the § 2B1.1(b)(9)(C) enhancement.

In sum, the parties disagree on two points. First, whether § 2B1.1(b)(9)(C) applies even though the Order did not expressly enjoin Mr. Iley from committing the same or similar fraudulent conduct for which he ultimately was convicted. And, second, whether the fact that the Order imposed discipline on Mr. Iley for negligent conduct meant that Mr. Iley's subsequent commission of the same or similar conduct fraudulently was not in contravention of the Order.

A

As to the first question, having carefully considered our caselaw, the plain terms of § 2B1.1(b)(9)(C) and its commentary, and relevant authorities of our sister circuits, we conclude that, at least under the specific circumstances of this case, § 2B1.1(b)(9)(C) applies even though the Order did not expressly enjoin Mr. Iley from defrauding his clients. In particular, we conclude that § 2B1.1(b)(9)(C) may apply without an explicit injunction when, as here, the prior order (1) imposed a concrete punishment, such as a fine, on the defendant for the same or similar conduct at issue in the defendant's subsequent offense; (2) imposed prospective, remedial conditions or obligations, like practice monitoring and the filing of quarterly reports-through a probationary term or otherwise-that were reasonably calculated to curtail future instances of the conduct at issue; and (3) nevertheless the defendant perpetrated that prohibited conduct while the order was still in effect.

Importantly, we find persuasive support for our holding in our own precedent, specifically Pentrack . There, Mr. Pentrack and a state agency entered into a consent order. The order punished Mr. Pentrack for deceiving customers and enjoined him from, inter alia , making future "false, deceptive, or misleading statements." 428 F.3d at 988. Some years later, Mr. Pentrack was convicted of defrauding customers. After the district court enhanced his sentence under the Prior Order enhancement, Mr. Pentrack argued on appeal that the earlier order was not "specific" enough because "it merely obligated him to do what he had always been required to do, namely obey the law." Id. at 989.

In rejecting that argument, we undertook an informative examination of the history of the enhancement and its commentary.6 We did so because, though the enhancement requires the violation to be of a "specific" injunction-and in legal parlance that would mean the order "must be explicit"-the Prior Order enhancement's plain terms offered "little insight into exactly how the injunction must satisfy" the explicitness standard. Id. We noted that the Sentencing Commission inserted in 2000 the "prior, specific" language into what is in material respects the current *1282text of the Guideline,7 but notably we did not conclude that the Commission did so to create a heightened standard of specificity for injunctions falling within the ambit of the enhancement. In other words, we did not conclude that the Commission sought to ensure, by its word changes, that defendants would be subject to the enhancement only for violating express commands not to engage in certain conduct. See id. at 990.

Instead, examining the Commission's explanation for the insertion of the language, we noted the following: "The additional phrasing, then, merely clarifies the distinction between enhancements for bankruptcy and non-bankruptcy fraud, effectively leaving unaltered the application of the enhancement in non-bankruptcy proceedings." Id. (emphasis added). Under this unaltered application, the prior injunction need not have explicitly proscribed a defendant's subsequent offense conduct; rather, for purposes of the enhancement's application, we concluded that the injunction was sufficient, so long as it was "specific enough to provide the defendant with adequate notice of the prohibited conduct." Id.

We concluded that the order in Pentrack did just that. More specifically, "the order was designed to prohibit prior misconduct of the very same nature as [the defendant's] federal crimes (deception of consumers) and gives specific notice as to prohibited conduct"; therefore, we concluded that the order "satisfie[d] the requirements" of the Prior Order enhancement. Id. at 990-91. Given the adequate notice provided by the order, we thought Mr. Pentrack could "hardly complain that he did not know what past conduct was being enjoined or what future conduct would violate [the order's] terms." Id. at 991 n.3. For those reasons, we held that the district court did not err in enhancing Mr. Pentrack's sentence.

Pentrack suggests that an express injunction is not always necessary under § 2B1.1(b)(9)(C). Pentrack 's analysis of the enhancement's history and the Sentencing Commission's insertion of the phrase "prior, specific" indicates that those words were not aimed at creating a heightened standard of specificity for injunctions properly falling within the ambit of the enhancement. That is, the Commission was not seeking to ensure that defendants would be subject to the enhancement only if they violated express commands not to engage in certain conduct. Rather, we concluded that it is sufficient "if the injunction is specific enough to provide the defendant with adequate notice of the prohibited conduct." Id. at 990.

It is noteworthy, moreover, that in determining that the order was indeed specific enough in Pentrack , we did not parse its terms but rather focused on whether, overall, "the order was designed to prohibit prior misconduct of the very same nature as [Mr. Pentrack's] federal crimes," and whether the order "provide[d] [him] with adequate notice of the prohibited conduct"-that is, of "what future conduct would violate [the order's] terms." Id. at 990-991 & n.3. Viewed in totality, Pentrack 's reasoning thus strongly suggests that a prior order that was reasonably calculated to prohibit certain conduct need not include terms that expressly enjoin the future occurrence of that conduct. Rather, it is sufficient if that order gave the defendant adequate notice of the prohibited conduct and, in the words of the Guidelines commentary, the defendant's subsequent *1283offense conduct is "the same or similar" as the conduct that the order prohibited. U.S.S.G. § 2B1.1(b)(9)(C) cmt. background; see Pentrack , 428 F.3d at 990-991.

Viewed in this light, Pentrack points toward our ultimate conclusion that the district court did not err in applying § 2B1.1(b)(9)(C) to Mr. Iley, even though the Order lacked an explicit injunction against the commission of the fraudulent acts that were the subject of Mr. Iley's subsequent offense. As in Pentrack , the Order was reasonably calculated to prohibit conduct that was the same as or similar to Mr. Iley's subsequent offense conduct. Recall that the Order specifically identified the conduct: "Despite taking possession of sufficient funds to pay the taxes due, Respondent Iley failed to properly and promptly remit payment in full to the IRS...." R., Vol. I, at 88. Subsequently, Mr. Iley was indicted, inter alia , for similar conduct, i.e., taking client funds that were made available to pay taxes, failing to remit those funds to the IRS, and instead "us[ing] these monies for other purposes, including paying personal expenses such as payments on his mortgage and his wife's credit card bill." Id. at 7. To prohibit this conduct, the Order imposed on Mr. Iley a substantial fine of $10,000 and a probationary term during which he was required to abide by certain conditions.

Notably, to "improve the quality and accuracy of [his] tax services" and "to determine whether [he] meets the generally accepted professional standards for tax services," including adhering to the Board's ethical rules, the Order required Mr. Iley to submit to monitoring of his practice by a third-party accountant. Id. at 93. Furthermore, under the Order, Mr. Iley was obliged to submit quarterly reports to the Board in which, among other things, he was required to attest that he was "in compliance with" the Order-that is, the same Order that condemned his conduct of taking and not remitting client money. Id. at 95. At a minimum, then, the Order's monetary fine and forward-looking remedial obligations evince that the parties to the Order contemplated that, while on probation, Mr. Iley would cease the conduct that had given rise to the Order-even without an explicit injunction mandating that he do so. In other words, the Order was reasonably calculated to prohibit conduct that was the same as or similar to Mr. Iley's subsequent offense conduct. But Mr. Iley did not stop the conduct.

Furthermore, as in Pentrack , the Order clearly provided Mr. Iley "with adequate notice" that this conduct was "prohibited." 428 F.3d at 990. Like Mr. Pentrack, Mr. Iley could "hardly complain that he did not know" that his later fraud contravened the substance of the Order. Id. at 991 n.3. Simply put, Mr. Iley knew the Order prohibited the same or similar conduct comprising his fraudulent scheme but he kept engaging in that conduct anyway, and, as a consequence, his clients were defrauded. Thus, given the Order's notice and Mr. Iley's subsequent conduct evidencing defiance of the Order, Pentrack is persuasive support for the conclusion that the district court properly determined-even without an express injunction-that Mr. Iley's conduct "satisfies the requirements of § 2B1.1(b) ( [9] )(C)." Id. at 991.

To be sure, as Mr. Iley is quick to point out, the order in Pentrack differs from the Order here because it "specifically enjoined fraud." Aplt.'s Opening Br. at 12. As such, though Pentrack 's reasoning is quite persuasive and illuminating, we freely acknowledge that, standing alone, Pentrack does not directly control our holding here. In short, standing alone, Pentrack is not dispositive. However, Pentrack does not stand alone. Our holding-which is grounded in the specific circumstances of Mr. Iley's case-finds further support in the decisions of our sister circuits.

*1284In the Fifth Circuit's decision in United States v. Nash , 729 F.3d 400 (5th Cir. 2013), for example, an agency determined that Mr. Nash improperly accepted food stamps for unapproved items. The agency then imposed a fine and sent Mr. Nash a warning letter-a letter that the court consistently referred to as the "July 9 letter." See, e.g. , id. at 405. That letter "warned that failure to pay the fine would result in a six-month disqualification from" the food-stamp program and "made clear that imposition of the fine did not preclude further action in response to [Mr.] Nash's violations." Id. at 405, 406. Mr. "Nash acknowledged the violation and agreed to pay the fine." Id. at 402. But he nevertheless continued to accept food stamps for unauthorized items. Mr. Nash was ultimately indicted and convicted of a criminal offense stemming from his food-stamp fraud. The district court applied the § 2B1.1(b)(9)(C) enhancement in sentencing Mr. Nash, and he challenged this ruling on appeal.

At the outset, the Fifth Circuit defined Mr. Nash's challenge and its disposition: "We understand [Mr. Nash] to argue that because the July 9 letter did not expressly enjoin him from committing food stamp fraud in the future, he cannot now be found to have violated the [agency's] order. We find [Mr.] Nash's argument to be without merit." Id. at 404. Focusing on the substance of § 2B1.1(b)(9)(C),8 the Fifth Circuit concluded that the "application of the enhancement 'requires some specific directive that the defendant can defy.' " Id. at 405 (quoting United States v. Goldberg , 538 F.3d 280, 292 (3d Cir. 2008) ). And the July 9 letter was such a directive because it effectively warned Mr. Nash "that continuation of his fraudulent conduct was illegal." Id. at 406. The court opined that, while " 'no court of appeals has held that a mere warning letter, without more, can justify the enhancement,' the fine (itself the result of a proceeding in which [Mr.] Nash participated) clearly 'ordered [Mr. Nash] to stop' committing food stamp fraud." Id. (quoting Goldberg , 538 F.3d at 291-92 ). And, because Mr. Nash defied this order to stop, the Fifth Circuit concluded that Mr. Nash was "exactly the type of defendant the enhancement was intended to apply to"-that is, "one 'who has ... demonstrate[d] aggravated criminal intent.' " Id. (second alteration in original) (quoting § 2B1.1(b)(9)(C) cmt. background). Thus, the Nash court held that § 2B1.1(b)(9)(C) applied even though the July 9 letter did not expressly enjoin Mr. Nash from committing the specific fraudulent conduct for which he later was criminally prosecuted.

It is patent that Nash bolsters the ultimate conclusion that we reach here. Like in Nash , Mr. Iley's contention that the enhancement does not apply because the Order did not explicitly enjoin him from engaging in the fraudulent conduct underlying his offense is "without merit." Id. at 404. Analogous to Nash , Mr. Iley was warned, in substance, through the Order "that continuation of his fraudulent conduct" was prohibited. Id. at 406. Specifically, the Order identified the acts of Mr. Iley that it sought to prohibit, including "taking possession of sufficient [client] funds to pay the taxes due" and then not "properly and promptly" paying those funds to the IRS. R., Vol. I, at 88. These were the same *1285basic acts underlying Mr. Iley's fraudulent scheme. And, partly because of these acts, the Order fined Mr. Iley and placed him on probation, during which Mr. Iley was required to abide by certain conditions. Those conditions included practice monitoring and the requirement that he attest quarterly that he was "in compliance with" the Order-that is, an Order that condemned his conduct of taking and not remitting client money. Id. at 95. We are able quite naturally to read the Order's sanctions, including its monetary fine and forward-looking remedial obligations, as a firm and concrete warning to Mr. Iley to stop the conduct that had given rise to the Order. Further, as in Nash , the Order's sanctions here-viewed in totality-constituted a "specific directive that the defendant can defy." Nash , 729 F.3d at 405 (quoting Goldberg , 538 F.3d at 292 ). And, by continuing to engage in the kind of acts that the Order identified as worthy of sanction, Mr. Iley certainly did defy the Order's directive. Thus, as in Nash , Mr. Iley's subsequent fraudulent conduct made "him exactly the type of defendant the enhancement was intended to apply to." Id. at 406.

Nash distinguished circuit cases holding that a mere warning letter, without more, was insufficient to justify application of the enhancement. Id. It noted that more was present in Nash ; "the fine (itself the result of a proceeding in which [Mr.] Nash participated) clearly 'ordered [Mr. Nash] to stop' committing food stamp fraud." Id. (quoting Goldberg , 538 F.3d at 291-92 ).9 Like Nash , we also can distinguish such *1286cases because there is more here-indeed, there is more here than in Nash .

We need not, and thus do not, rely solely on a monetary fine (as in Nash ) to distinguish such mere-warning cases. To be sure, the Order clearly imposed a substantial fine on Mr. Iley (i.e., $10,000), and it is a significant part of the calculus. But we also may rely here on the Order's imposition of a probationary term on Mr. Iley that had prospective, mandatory conditions. Coupled with the fine, these conditions were reasonably calculated to send the definite and concrete message to Mr. Iley that he should cease the conduct that had given rise to the Order-or, as Nash put it, that Mr. Iley should "stop" this conduct. Id. (quoting Goldberg , 538 F.3d at 291-92 ). Thus, Nash stands with our decision in Pentrack in supporting the conclusion that we reach here.10

*1287We can say the same thing with respect to the Eighth Circuit's decision in United States v. Jokhoo , 806 F.3d 1137 (8th Cir. 2015). There, a state agency issued administrative orders that revoked Mr. Jokhoo's business license and imposed "civil penalties after a hearing" on him for various fraudulent practices. Id. at 1139. Mr. Jokhoo nevertheless continued the same or similar practices and was subsequently indicted and convicted for doing so. At sentencing, the district court enhanced Mr. Jokhoo's sentence under § 2B1.1(b)(9)(C) -a decision that he challenged on appeal. The Eighth Circuit discerned no error in the enhancement, however. Citing Nash , it stated, "[t]he administrative order need not expressly enjoin proscribed conduct, but must direct a defendant to refrain from such conduct." Id. at 1141. The Eighth Circuit reasoned that, like the fine in Nash , the agency's "sanctions 'clearly ordered' [Mr.] Jokhoo to stop committing fraud, but the record shows that [he] continued to do so." Id. (quoting Nash , 729 F.3d at 406 ). And so the Eighth Circuit in Jokhoo held that "[t]he district court ... did not err in applying the enhancement." Id.

Jokhoo 's application here is clear: it further undermines Mr. Iley's claim that § 2B1.1(b)(9)(C) cannot apply because the Order did not expressly enjoin him from defrauding his clients. Indeed, the Eighth Circuit directly rejected such a notion, stating that a prior "order need not expressly enjoin proscribed conduct." Id. Like Nash , the Jokhoo court found that the sanctions imposed on Mr. Jokhoo-including civil penalties-were sufficient to order him to stop his fraudulent conduct. The same is true here. Coupled with its $10,000 fine, the Order's forward-looking remedial obligations were reasonably calculated to send a definite and concrete message to Mr. Iley that he should cease (i.e., stop) the conduct that had given rise to the Order. But Mr. Iley did not stop. Consequently, as the court did in Jokhoo , we conclude that the district court rightly imposed the enhancement on Mr. Iley.

Mr. Iley musters little caselaw in favor of a contrary result. As noted, he has pointed out that the order in Pentrack differs from the Order here because it "specifically enjoined fraud." Aplt.'s Opening Br. at 12. But, as discussed supra , that fact ultimately does little for Mr. Iley. We have acknowledged that the different facts in Pentrack mean that, standing alone, that case is not dispositive. As demonstrated, however, Pentrack does not stand alone; persuasive circuit precedent like Nash and Jokhoo supports the conclusion that we reach here. The only other case involving application of the enhancement that Mr. Iley affirmatively relies on to support his first argument is our decision in United States v. Lewis , 594 F.3d 1270 (10th Cir. 2010). Mr. Iley says that in Lewis "[t]his Court sustained the enhancement 'because some transactions in the Ponzi scheme violated' the 'order issued by the Nebraska Department of Banking and Finance.' " Aplt.'s Opening Br. at 13 (quoting Lewis , 594 F.3d at 1287 ). Mr. Iley's reliance on Lewis , however, is misguided. In the language from Lewis that Mr. Iley quotes as ostensibly stating the court's holding, the Lewis panel is actually describing the district court's rationale for imposing the enhancement-not the rationale of the Lewis panel. See Lewis , 594 F.3d at 1287 ("The district court imposed this enhancement because some transactions in the Ponzi scheme violated a cease-and-desist order issued by the Nebraska *1288Department of Banking and Finance."). And neither the argument that the Lewis defendant presented to the district court nor the one he raised on appeal is even remotely relevant to the matters at issue here: "In the district court Lewis opposed the two-level enhancement on the ground that the violation of the order was not foreseeable. His argument on appeal is different. He now argues that the enhancement should not apply because he did not have knowledge of the order." Id. at 1288. In short, Lewis is inapposite. Thus, Mr. Iley's reliance on it is unavailing.

Mr. Iley does not fare much better by asserting that "the guideline's commentary ... indicate[s] that circumstances like Mr. Iley's are outside the scope of § 2B1.1(b)(9)(C)" because it "confirm[s] that the guideline applies only where the defendant violated the express terms of a prior order." Aplt.'s Opening Br. at 11 (emphasis added). Mr. Iley notes that the one illustrative hypothetical in the commentary provides that "a defendant whose business previously was enjoined from selling a dangerous product, but who nonetheless engaged in fraudulent conduct to sell the product, is subject to this enhancement." U.S.S.G. § 2B1.1(b)(9)(C) cmt. n.8(C). However, Mr. Iley offers no argument to explain why we should view this hypothetical as helpful to him. Indeed, the hypothetical tells us nothing about the nature of the prior order that enjoined the sale of the dangerous product. Notably, notwithstanding Mr. Iley's conclusory suggestion to the contrary, see, e.g. , Aplt.'s Reply Br. at 9, the hypothetical does not tell us whether the prior order that enjoined the sale did so by it express terms or, as here, by its substance-viz. , by being "designed to prohibit prior misconduct of" the same or similar sort as the defendant's subsequent criminal conduct and by being "specific enough to provide the defendant with adequate notice of the prohibited conduct." Pentrack , 428 F.3d at 990-91. Therefore, the hypothetical does not advance Mr. Iley's cause.

Mr. Iley also posits that "[t]he commentary further states that the guideline applies when the defendant's fraud contravened a directive 'to take or not to take a specified action.' " Aplt.'s Opening Br. at 12 (quoting U.S.S.G. § 2B1.1(b)(9)(C) cmt. n.8(C) ). But, again, Mr. Iley does not explain why the quoted commentary language helps him. More specifically, he does not tell us why any such directive to take or not take such action must itself be set out in explicit terms, if the directive's substance-like the Order's substance here-is "specific enough to provide the defendant with adequate notice of the prohibited conduct," Pentrack , 428 F.3d at 990, and reasonably calculated to send the definite and concrete message to the defendant that he should cease (i.e., stop) the conduct that gave rise to the order. Moreover, in its analysis of the enhancement's history, the Pentrack court concluded that the "specified action" language was part of the "additional phrasing" that "merely clarifies the distinction between enhancements for bankruptcy and non-bankruptcy fraud." Id. Therefore, it does not seem that this language was ever intended to shed any particular light on whether a defendant's subsequent criminal conduct must violate the express terms of a prior injunction to qualify for the § 2B1.1(b)(9)(C) enhancement. Indeed, importantly, this language did not stop the Pentrack panel from concluding that central to the specificity inquiry is simply whether "the injunction is specific enough to provide the defendant with adequate notice of the prohibited conduct." Id. And, as noted, the Order here was specific enough for this purpose. In sum, the Guidelines commentary also lends Mr. Iley no succor.

In summary, we hold that, at least under the specific circumstances of this case, *1289§ 2B1.1(b)(9)(C) applies even though the Order did not expressly enjoin Mr. Iley from defrauding his clients. In particular, we conclude that § 2B1.1(b)(9)(C) may apply without an explicit injunction when, as here, the prior order (1) imposed a concrete punishment, such as a fine, on the defendant for the same or similar conduct at issue in the defendant's subsequent offense; (2) imposed prospective remedial conditions or obligations, like practice monitoring and the filing of quarterly reports-through a probationary term or otherwise-that were reasonably calculated to curtail future instances of the conduct at issue; and (3) nevertheless the defendant perpetrated that prohibited conduct while the order was still in effect.11

B

We now take up the second question: Whether Mr. Iley's fraudulent conduct violated the Order where it expressly only punished him for negligent conduct. Mr. Iley claims that his offense conduct did not violate the Order "[b]ecause negligence is not similar conduct to fraud." Aplt.'s Reply Br. at 14 n.4. He maintains that, just as "a dog distinguishes between being stumbled over and being kicked," we should distinguish between negligence and fraud. Id. at 13 (quoting Oliver Wendell Holmes Jr., THE COMMON LAW at 3 (1881) ). In more prosaic language, he contends that "a warning against being sloppy" does "not amount to a warning not to steal clients' money." Id. at 14 n.4. Thus, Mr. Iley argues that by defrauding his clients, he did not violate the Order's "warning against being sloppy." Id.

But, importantly, Mr. Iley offers us no reason to read a symmetry-of-mental-state requirement into § 2B1.1(b)(9)(C), or any on-point legal authority that would support such a step. And there is reason to question whether the Sentencing Commission contemplated such a significant limitation on the universe of defendants qualifying for the enhancement. Cf. U.S.S.G. § 2B1.1 cmt. n.8(C) (setting forth a hypothetical illustrating the enhancement's application that ascribes no particular mental state to the prior conduct that gave rise to an injunction-involving the sale of a dangerous product-but that nevertheless deems the enhancement appropriate where the defendant is expressly described as engaging in "fraudulent conduct to sell the [same or similar dangerous] product").

Indeed, in this regard, a defendant who commits certain conduct with a high level of culpable intent after being formally warned against committing the same underlying conduct, while possessing a lower level of culpable intent, would seem to be even more worthy of the enhancement than a defendant who simply engages in the same prohibited conduct again, while possessing the same, lower level of culpable intent. That is because such a defendant seemingly would have displayed even more of the "aggravated criminal intent" that § 2B1.1(b)(9)(C) aims to punish. U.S.S.G. § 2B1.1 cmt. background. Put another way, that defendant would seemingly be more worthy of the enhancement because, not only would his subsequent criminal conduct indicate that the prior order did not deter him from engaging in the same prohibited conduct with the same level of culpable intent, but it also did not deter him from brazenly upping his game-viz. , from engaging in the same or *1290similar prohibited conduct with a higher level of "aggravated criminal intent." Id.

In this case, Mr. Iley evinced such brazen, and thus more sanction-worthy, conduct. The Order warned him that negligently harming his clients by taking their money ostensibly to pay their taxes to the IRS and then not doing so was prohibited and merited punishment and intrusive probationary conditions, like practice monitoring. Then, while still on probation for this negligent conduct, Mr. Iley fraudulently misrepresented to his clients that he was taking their money to pay their taxes to the IRS and then knowingly diverted the money for other personal uses. That is, Mr. Iley engaged in essentially the same or similar conduct when perpetrating his fraudulent scheme-the only critical difference being that, after being formally warned against doing so, he acted anyway with an even more culpable state of mind (i.e., fraudulently). As such, the district court certainly did not err in ruling that Mr. Iley acted with the kind of "aggravated criminal intent" that § 2B1.1(b)(9)(C) penalizes. Id. In other words, we hold that Mr. Iley's fraudulent conduct in not paying his clients' funds (as promised) to the IRS could and did violate the Order, even though by its explicit terms the Order only sanctioned Mr. Iley for his negligent commission of the same or similar acts.

IV

In conclusion, for the foregoing reasons, the district court did not err in applying the two-level enhancement under § 2B1.1(b)(9)(C) in Mr. Iley's case. Accordingly, we AFFIRM the court's sentencing order.

HARTZ, J., Circuit Judge, concurring.

I concur in the judgment and all of Judge Holmes's fine opinion except the discussion of United States v. Nash , 729 F.3d 400 (5th Cir. 2013), and United States v. Jokhoo , 806 F.3d 1137 (8th Cir. 2015). In particular, I agree with the opinion's determination that the context of the Order of the Colorado Board of Accountancy made clear that the fraudulent conduct of which Defendant was later convicted would be a violation of the terms of his probation under the Order.

In my view, Judge Holmes's opinion is fully convincing without any need for support from Nash and Jokhoo . And I think those two decisions are misguided because they in essence transform USSG § 2B1.1(b)(9)(C) into a recidivist provision, increasing a defendant's offense level simply because the defendant had previously been penalized by a court or administrative agency for similar misconduct. See Nash , 729 F.3d at 406-07 (Garza, J., dissenting). I am therefore reluctant to embrace the reasoning that brought those courts to their holdings (even though Judge Holmes's opinion is careful not to endorse the holdings in the two cases).