Epsilon Electronics, Inc. v. United States Department of the Treasury

Opinion concurring in part and dissenting in part filed by Senior Circuit Judge SILBERMAN.

GRIFFITH, Circuit Judge:

In 1995, President Clinton imposed trade sanctions against Iran that are enforced by the Office of Foreign Assets Control within the Department of the Treasury. OFAC is authorized to impose civil penalties against any person who exports goods to a third party who it has reason to know intends to send them to Iran. The principal question raised by this appeal is whether OFAC must also show that the goods actually ended up in Iran. We agree with the agency that the government need not make that showing and affirm the district court on that ground. But we also conclude that OFAC did not adequately explain parts of its determination that the exporter here had reason to know that its shipments would be sent on to Iran.

I

When the President identifies an “unusual and extraordinary threat” to the American economy, national security, or foreign policy that originates from abroad, see 50 U.S.C. § 1701, the International Emergency Economic Powers Act authorizes him to declare a national emergency and address the threat by regulating foreign commerce, see id. § 1702. In 1995, President Clinton determined that Iran’s “support for international terrorism, its efforts to undermine the Middle East peace process, and its efforts to acquire weapons of mass destruction” represented a national emergency, see Iranian Transactions Regulations, 77 Fed. Reg. 64,664, 64,664 (Oct. 22, 2012), and, invoking his authority under the Act, imposed comprehensive trade sanctions on Iran by executive order, see Exec. Order No. 12,959, 60 Fed. Reg. 24,757, § 1 (May 6,1995).

OFAC implemented the President’s executive order in September 1995 by promulgating the Iranian Transactions and Sanctions Regulations, see 60 Fed. Reg. 47,061 (Sept. 11,1995), which are now codified, as amended, at 31 C.F.R. pt. 560. Among other prohibitions, the regulations forbid “the exportation, reexportation, sale, or supply, directly or indirectly ... of any goods, technology, or services to Iran” by United States individuals and busi*917nesses, including exportation to a third country with “knowledge or reason to know” that the goods are “intended specifically” for reexportation to Iran. See 31 C.F.R. § 560.204.

The agency has invoked that prohibition against appellant Epsilon Electronics, a California-based wholesaler of sound systems, video players, and other accessories for cars. The company’s wares can be found across the globe, from Latin America to Africa and the Middle East. Asra International Corporation, a distributor based in Dubai, has been one of Epsilon’s trading partners. Between 2008 and 2012, Epsilon sent thirty-nine shipments of consumer goods to Asra, valued at about $3.4 million.

OFAC began investigating Epsilon in 2011, when the agency learned about a 2008 shipment from Epsilon’s California headquarters to an address in Tehran, Iran. In response to an administrative subpoena, Epsilon’s president denied knowledge of the shipment and suggested that a lower-level employee had sent the package without the company’s knowledge.

Later in 2011, OFAC also learned that Epsilon had received multiple wire transfers from a Dubai bank, made on behalf of Asra International. The agency examined Asra’s website, which touted the company’s success in the Iranian market, contained a directory of dealers who were all located in Iran, and displayed photos from trade shows in various Iranian cities. Some of these photos also appeared on Epsilon’s website. OFAC suspected that the company’s shipments to Asra were “destined for Iran,” and opened a second investigation on Epsilon in December 2011. The agency issued an administrative subpoena to Epsilon’s bank, seeking information about the company’s transactions with Asra.

In the meantime, OFAC decided to close its investigation of the 2008 shipment. In January 2012, the agency sent Epsilon a letter explaining that the shipment appeared to have violated OFAC regulations, and warning that those regulations “prohibit virtually all” American trade with Iran. Appellant’s App. [A.A.] 94. OFAC explained that it would not penalize Epsilon for the shipment but that the agency could take this apparent violation into account in any future case.

But OFAC did not close its parallel investigation of Epsilon’s dealings with Asra. In May 2012, the agency sent Epsilon another administrative subpoena, requesting further details on the company’s transactions with Asra and with Iran. Epsilon responded that it had no dealings with Iran and that none of its shipments to Asra were intended for Iran. The company submitted invoices chronicling thirty-four shipments to Asra.

Between February and May 2012, while OFAC’s investigation continued, Epsilon sent Asra five more shipments. During this period, Epsilon managers corresponded by email with an Asra manager, Shahriar Hashemi, who described plans to launch a Dubai retail store under “Asra’s flag.” A.A. 118. The emails record Hashemi and Epsilon negotiating several orders, and show Hashemi mentioning plans for his showroom, complaining about another Dubai shop selling Epsilon products, worrying about whether Epsilon products could endure Dubai’s heat, and anticipating sales to African and Central Asian customers. An Epsilon manager promised Hashemi that the Dubai retail market was “all yours.” See A.A. 119.

In May 2014, OFAC tentatively concluded that all thirty-nine of Epsilon’s shipments to Asra violated 31 C.F.R. § 560.204 because each was made with knowledge, or reason to know, that Asra intended to reexport the goods to Iran. The agency sent Epsilon a Prepenalty Notice, declaring its intent to impose a civil monetary *918penalty of $4,073,000, subject to Epsilon’s response. OFAC arrived at that dollar amount by applying its penalty guidelines, which required the agency to determine whether any of the violations were voluntarily disclosed and whether any were “egregious.” See generally 31 C.F.R. pt. 501, App. A. OFAC found that none of Epsilon’s violations was voluntarily disclosed, and that the last five shipments, made after Epsilon received OFAC’s January 2012 cautionary letter, were egregious. Though the agency has authority to depart upward or downward from the guideline penalty, it decided not to do so after balancing the aggravating and mitigating factors.

In July 2014, OFAC issued a final Penalty Notice, formally imposing a $4,073,000 civil penalty. The agency had not been persuaded by Epsilon’s response to the Prepenalty Notice, which again denied any knowledge or reason to know that Asra distributed Epsilon’s products in Iran. The Penalty Notice explained that “multiple facts tend to show that the goods exported to Asra were sent to Iran and that Epsilon knew or had reason to know that the goods were intended specifically for supply, transshipment, or reexportation, directly or indirectly, to Iran.” Although the Notice recited much of the evidence against Epsilon, it never mentioned the emails between Epsilon management and Hashemi.

The issuance of the Penalty Notice was final agency action. See 31 C.F.R. § 560.704. In December 2014, Epsilon sued OFAC in district court. Epsilon’s complaint sought declaratory and injunc-tive relief against enforcement of the civil penalty. On March 7, 2016, the district court granted summary judgment in favor of the government. See Epsilon Elecs., Inc. v. U.S. Dep’t of Treasury, 168 F.Supp.3d 131, 147 (D.D.C. 2016).1

Epsilon timely appealed. We have jurisdiction under 28 U.S.C. § 1291, and review de novo the district court’s entry of summary judgment in favor of the government. Islamic Am. Relief Agency v. Gonzales (JARA), 477 F.3d 728, 732 (D.C. Cir. 2007). As the Administrative Procedure Act requires, our review is “highly deferential” to the agency, meaning we may set aside OFAC’s action “only if it is arbitrary, capricious, an abuse of discretion, or otherwise not in accordance with law.” IARA, 477 F.3d at 732 (quoting 5 U.S.C. § 706(2)(A)). Under that standard, we will uphold agency findings that are supported by substantial evidence, even if we might have reached a different conclusion in the first instance. See, e.g., United Steel Workers Int’l Union v. Pension Benefit Guar. Corp., 7Ó7 F.3d 319, 325 (D.C. Cir. 2013). That deference has a caveat: although the APA does not permit us to substitute our judgment for the agency’s, we must ensure that the agency has “articulate[d] a satisfactory explanation for its action including a ‘rational connection between the facts found and the choice made.’ ” Motor Vehicle Mfrs. Ass’n of the U.S. v. State Farm Mut. Auto. Ins. Co., 463 U.S. 29, 43, 103 S.Ct. 2856, 77 L.Ed.2d 443 (1983) (quoting Burlington Truck Lines, Inc. v. United States, 371 U.S. 156, 168, 83 S.Ct. 239, 9 L.Ed.2d 207 (1962)).

Epsilon asks us to set aside these fundamental doctrines of administrative law by reviewing OFAC’s decision de novo instead of under the APA’s arbitrary-and-eapri-cious standard. We have described de novo *919review in an APA case as “extraordinary and rare,” so rare, in fact, that we have never done so. Zevallos v. Obama, 793 F.3d 106, 112 (D.C. Cir. 2015). Although dicta in one of our cases left the door open to such scrutiny where the agency’s fact-finding procedures are “severely defective,” Nat’l Org. for Women v. Soc. Sec. Admin., 736 F.2d 727, 745 (D.C. Cir. 1984) (Mikva & McGowan, JJ., concurring), we need not decide what such an analysis would entail, because Epsilon failed to preserve any argument for de novo review before the district court. See Mem. Supp. Pl.’s Mot. in Opp’n to Defs.’ Mot. Summ. J. 9, Epsilon, 168 F.Supp.3d 131 (No. 14-2220 (RBW)), ECF No. 19-1 [hereinafter Epsilon Mot. Summ. J.].2 Accordingly, we will adhere to the “arbitrary [and] capricious” standard set out in 5 U.S.C. § 706(2)(A).

II

Epsilon offers three challenges to the civil penalty that OFAC imposed. First, the company contends that none of its thirty-nine shipments to Asra were in violation of the Iranian Transactions and Sanctions Regulations. Second, Epsilon claims that the amount of the penalty assessed is not only arbitrary and capricious, but also an “excessive fine” forbidden by the Eighth Amendment. Third, the company argues that its due process rights were violated because it had insufficient notice of the evidence that OFAC intended to rely on.

A

We first consider whether OFAC properly found Epsilon liable for thirty-nine violations of section 560.204 of the Iranian Transactions and Sanctions Regulations. In addressing that issue, we face a threshold question of regulatory interpretation. To hold a party liable for a breach of section 560.204, must OFAC prove that goods shipped by that party actually arrived in Iranian territory? Or can liability rest solely on a showing that the party shipped goods to a third party, with reason to know that the recipient specifically intended to reexport them to Iran?

Epsilon advances the former position, and contends there is no substantial evidence that the thirty-nine shipments at issue ever entered Iran. OFAC responds that the regulation’s plain text does not require such a showing. See Appellee Br. 29 (“Under the unambiguous terms of the regulation, actual reexportation to Iran by the person in the third country is not required for a violation.”). The agency also urges us to defer to its interpretation if we find the regulation ambiguous. See Auer v. Robbins, 519 U.S. 452, 461, 117 S.Ct. 905, 137 L.Ed.2d 79 (1997). However, the reading 'of section 560.204 that OFAC has adopted is the same reading that we would have adopted in the absence of any agency interpretation. We therefore need not decide whether Auer deference would be appropriate in this instance.3

*920i

We begin with the regulation’s text. See In re England, 375 F.3d 1169, 1177 (D.C. Cir. 2004). Section 560.204 provides:

Except as otherwise authorized pursuant to this part ... the exportation, reexportation, sale, or supply, directly or indirectly, from the United States, or by a United States person, wherever located, of any goods, technology, or services to Iran or the Government of Iran is prohibited, including the exportation, reexportation, sale, or supply of any goods, technology, or services to a person in a third country undertaken with knowledge or reason to know that:

(a) Such goods, technology, or services are intended specifically for supply, transshipment, or reexportation, directly or indirectly, to Iran or the Government of Iran....

The analysis at first glance appears straightforward. The regulation prohibits “the exportation [] of any goods [] to a person in a third country undertaken with knowledge or reason to know that [s]uch goods [ ] are intended specifically for [ ] reexportation [] to Iran.” See id. That prohibition, on its face, has only two elements: (1) the exportation of goods to “a person in a third country” and (2) “knowledge or reason to know” that the third-country recipient plans to send the goods on to Iran. Id. The goods’ actual arrival in Iran is not mentioned, meaning that proof of this event is not required for a liability finding under the prohibition on third-country exports.

Epsilon, in response, points to the word “including.” The rule just discussed is “in-clud[ed]” within a broader prohibition on “exportation ... to Iran.” See id. The company argues that the “word ‘including’ makes clear there is no separate prohibition on exports to third countries independent from reexportation to Iran.” Appellant Reply Br. 6. This argument relies on an unstated premise: that goods have not been exported “to Iran” until they actually reach Iranian territory. OFAC, by contrast, assumes that the phrase “to Iran” refers to the sender’s intent, not the ultimate arrival of the goods. In other words, on OFAC’s interpretation, goods have been “export[ed] ... to Iran” when the exporter puts them in transit, with Iran as the intended final destination.4

We think OFAC’s reading more closely aligns with ordinary English usage. Suppose you put a birthday card in the mail, addressed to your brother. While the card is still en route, your mother asks you, “Did you send a card to your brother?” In line with OFAC’s usage, you would respond, “I sent a card to him, but it hasn’t arrived yet,” because you put the card in transit, intending it to reach him. Following Epsilon’s usage, though, you would have to say, “I didn’t send a card to him,” because the card has not yet arrived. (Stranger still, if you were uncertain whether the card had reached his mailbox, you might answer, “I don’t know if I sent a *921card to him or not”) The first statement is more consistent with the way ordinary English speakers talk. Cf. Bond v. United States, — U.S.-, 134 S.Ct. 2077, 2090, 189 L.Ed.2d 1 (2014) (rejecting a linguistic usage that “no speaker in natural parlance” would employ).

The agency’s argument draws further support from the definition of the word “exportation” in export rules that are closely related to OFAC’s. The regulations in question are the Department of Commerce’s Export Administration Regulations (EAR) which control the export of items that have both civilian and military uses. See 15 C.F.R. § 730.3. The Iranian transaction regulations do not expressly incorporate this EAR definition, but they often refer to the EAR. For example, OFAC’s approval of some export activities is conditioned on compliance with the EAR. See, e.g., 31 C.F.R. §§ 560.530, 560.540. The EAR defines “export” as “an actual shipment or transmission of items out of the United States.” 15 C.F.R. § 772.1 (2014). In other words, the occurrence of an “export” is not contingent on the goods’ arrival at their final destination.. See id. What’s more, “the export or reexport of items subject to the EAR that will transit through [Country A] or be transshipped in [Country A] to [Country B] or are intended for reexport to [Country B], are deemed to be exports to [Country B].” Id. § 734.2(b)(6) (2014) (emphasis added).5 Note the use of forward-looking language: the export of items “that will transit” or “are intended for reexport.” If an exporter can say, “I have exported items to Country B that will transit through Country A,” then exportation to B occurs before “transit through” A, and thus before the goods reach A, let alone B. The EAR definition of “export” indicates that OFAC’s reading of section 560.204 reflects the meaning of that word as it is used in trade regulations.

The EAR, like OFAC’s interpretation of section 560.204, embodies the understanding, drawn from broader legal usage, that exportation is an “act,” specifically, “[t]he act of sending or carrying goods and merchandise from one country to another.” Exportation, Black’s Law Dictionary (10th ed. 2014). An “act,” in turn, is an actor’s voluntary conduct: for example, placing goods on a ship bound for Iran. See Act, Black’s Law Dictionary (10th ed. 2014) (“The word ‘act’ ... denote[s] an external manifestation of the actor’s will and does not include any of its results, even the most direct, immediate, and intended.” (quoting Restatement (Second) of Torts § 2 (1965))). If an exporter has taken all the steps he must personally take to put goods in transit to Iran, and the goods are out of his control, no further “voluntary conduct” or “external manifestation of [] will” by the exporter is necessary for the goods to arrive in Iran. See Restatement (Second) of Torts § 2 cmt. c (“Thus, if the actor, having pointed a pistol at another, pulls the trigger, the act is the pulling of the trigger and not the impingement of the bullet upon the other’s person.”). The arrival of the goods is a “result” of his “voluntary conduct,” not part of the conduct itself, and thus is not a component of the “act” of exportation.

Epsilon’s gloss on section 560.204 would also subvert the ordinary meaning of the word “including.” That word typically introduces one or more illustrative examples. See, e.g., Chickasaw Nation v. United States, 534 U.S. 84, 89, 122 S.Ct. 528, 151 L.Ed.2d 474 (2001); Dong v. Smithsonian Inst., 125 F.3d 877, 880 (D.C. Cir. 1997); see also Antonin Scalia & Bryan A. Gar*922ner, Reading Law 132-33 (2012). Whatever follows the word “including” is a subset of whatever comes before; any conduct that comes within the “including” clause comes, by definition, within the preceding clause as well. For example, imagine a regulation that reads: “All disruptive activity is prohibited in the park, including the playing of loud music.” The word “including” indicates that “playing of loud music” is part of the broader category of “disruptive activity.” And if a court (or an agency) adopted a definition of “disruptive activity” that excluded “playing of loud music” in many circumstances, that court (or agency) would distort the plain meaning of the regulation.

That principle guides us here, and further illustrates why Epsilon’s interpretation of the phrase “to Iran” cannot be correct. Section 560.204 is divided into two clauses. First is the prohibitory clause, which contains the general ban on “exportation ... to Iran.” Second is the “including” clause, which contains the specific prohibition on third-country shipments that is at issue in this case. If.we adopted the company’s reading of the words “exportation ... to Iran” in the prohibitory clause, certain conduct would be covered by the including clause, but not by the prohibitory clause. Consider a case where an exporter ships goods to a distributor in a third country, knowing that the distributor intends to send those goods on to Iran. In this hypothetical, there is no dispute that the goods entered the third country, but no showing that they actually made it to Iran. On Epsilon’s reading, such a case would satisfy the text of the including clause (because the goods arrived in the third country, and the exporter had the necessary mental state), but not the text of the prohibitory clause (because the goods did not arrive in Iran). That interpretation turns the word “including” on its head.

Of course, there are instances where the plain text of an including clause is limited in scope by the preceding clause. See Massachusetts v. EPA, 549 U.S. 497, 556-57, 127 S.Ct. 1438, 167 L.Ed.2d 248 (2007) (Scalia, J., dissenting). Justice Scalia’s dissent in Massachusetts cites several examples. But this situation only arises when a particular word or phrase from the first clause is implicitly carried forward into the second clause. For instance, a statute covering “any American automobile, including any truck or minivan” would be most naturally read to mean “any American automobile, including any [American] truck or minivan.” See id. at 557, 127 S.Ct. 1438. Similarly, the phrase “a proceeding in a foreign or international tribunal, including criminal investigations conducted before formal accusation” would “not encompass criminal investigations underway in a domestic tribunal” because the statutory language implicitly reads “a proceeding in a foreign or international tribunal, including criminal investigations conducted before formal accusation [in a foreign or international tribunal].” See id. (quoting 28 U.S.C. § 1782(a)).

Here, though, it’s not clear what word or phrase would carry forward from the prohibitory clause and limit the scope of the including clause. Perhaps it would be the words “to Iran” (assuming, as Epsilon does, that “to Iran” refers to arrival in Iran, not the sender’s intent). That proposition would be complicated by the fact that the .words “to Iran” already occur in the including clause: the exporter who ships to a third country must have “knowledge or reason to know” that the goods are intended for reexportation “to Iran.” 31 C.F.R. § 560.204(a). Bringing the words “to Iran” from the prohibitory clause into the including clause would also be odd in that the including clause already refers to shipment “to a person in a third country.” Should the clause be read to include ship*923ments “to a person in a third country to Iran undertaken with knowledge or reason to know”? That would be an awkward construction, to say the least. In the end, we see no reason to depart in this case from the usual rule that “including” means “for example.”

ii

Epsilon contends, in the face of the text, that OFAC has recognized a safe harbor in section 560.204: the “inventory exception.” This exception, according to the company, is “well understood in the industry as a negative reading of § 560.204, creating a safe harbor for re-exports to Iran of nonsensitive ..'. products so long as the U.S. exporter does not know, or have reason to know, such products are specifically intended for Iran.” Appellant Br. 14; see also Br. of Amicus Curiae JPM Legal Advisors 3 (describing the inventory exception as a “safe harbor that protects U.S. exporters from running afoul of the regulations where a third party in a non-sanctioned country reexports their goods to Iran without their knowledge or consent” (emphasis added)). Thus, Epsilon explains, if it ships goods to a Dubai company that are taken up into the Dubai company’s “general inventory,” Epsilon cannot be held liable if the Dubai company later ships those same goods to Iran.

Nobody argues that section 560.204 is a strict-liability rule. After all, liability for shipment of goods to a third country explicitly depends on the shipper’s knowledge or “reason to know” that the third-country recipient specifically intends to reexport those goods to Iran. See 31 C.F.R. § 560.204. Conversely, when an exporter does have reason to know that its third-country trading partner specifically intends to reexport the exporter’s goods to Iran, the exporter cannot avoid liability by asserting that the exports passed through the middleman’s “general inventory.” Appellant Br. 14. The regulation does not provide support for Epsilon’s proposed freestanding exception. Nor does the 2002 OFAC guidance document on which Epsilon and amicus rely. The guidance document merely restates section 560.204’s prohibition and “reason to know” standard, and is not framed as an “exception.”6 See Office of Foreign Assets Control, 020722-IR-01, Guidance on Transshipments to Iran (2002) [hereinafter Transshipments Guidance]. Epsilon thus was properly found liable for violating section 560.204 if it had reason to know that its shipments to Asra were specifically intended for reexport to Iran, regardless of whether Asra treated those shipments as “general inventory.”

iii

Our dissenting colleague argues that OFAC failed in its duty of reasoned deci-sionmaking because the agency’s Penalty Notice was ambiguous. One sentence in that Notice reads: “Multiple facts tend to show that the goods exported to Asra were sent to Iran and that Epsilon knew or had reason to know that the goods *924were intended specifically for supply, transshipment, or reexportation, directly or indirectly, to Iran.” A.A. 198 (emphasis added). In the dissent’s view, the “goods ... were sent to Iran” language suggests a finding that the goods did arrive in Iran, and thus indicates that OFAC was trying to avoid deciding whether the actual arrival of goods in Iran is necessary for a section 560.204 violation. But see discussion supra Section ILAi (explaining that the phrase “to Iran” more naturally refers to the sender’s intent, not the actual arrival of goods in Iran). The dissent contends that this ambiguity requires remand of all liability findings, but we disagree.

Under the APA’s deferential standard of review, we will uphold an agency decision where “the agency’s path may reasonably be discerned,” even if the decision is “of less than ideal clarity.” E.g., Casino Airlines, Inc. v. NTSB, 439 F.3d 715, 717 (D.C. Cir. 2006) (quoting Bowman Transp., Inc. v. Ark.-Best Freight Sys., Inc., 419 U.S. 281, 285-86, 95 S.Ct. 438, 42 L.Ed.2d 447 (1974)). Here, we can see the path without difficulty. The Prepenalty Notice, the first document that formally laid out OFAC’s charges against Epsilon and offered the company an opportunity to respond, set out the basis for the agency’s proposed violation findings in a distinct paragraph:

From on or about August 26, 2008, to on or about May 22, 2012, Epsilon appears to have violated 31 C.F.R. § 560.204 when it issued 39 invoices for car audio and video equipment, valued at $3,407,491, which was shipped to Asra, a company with offices in Tehran, Iran, and Dubai, U.A.E., that reexports most, if not all, of its products to Iran. Epsilon knew or had reason to know that such goods were intended specifically for supply, transshipment, or reexportation, directly or indirectly, to Iran.

Prepenalty Notice 1, A.A. 185. Like an indictment, this paragraph sets out the elements of a section 560.204 violation as the agency understood them, and makes no mention of the actual arrival of goods in Iran. The Prepenalty Notice based its allegation that Epsilon violated section 560.204 on just two premises: first, Epsilon shipped goods to a company “that reexports most, if not all, of its products to Iran” and second, Epsilon “knew or had reason to know” about Asra’s Iranian exports. See id. Far from “straddling the issue,” see Partial Dissent at 933, the Pre-penalty Notice clearly indicates that in the agency’s view, no showing that Epsilon’s goods had arrived in Iran was necessary for a section 560.204 violation finding.7 And because we can see exactly how the agency reasoned, a remand for clarification of that reasoning would serve no purpose. Cf. PDK Labs., Inc. v. DEA, 362 F.3d 786, 799 (D.C. Cir. 2004) (“If the agency’s mistake did not affect the outcome, if it did not prejudice the petitioner, it would be senseless to vacate and remand for reconsideration.”).

The dissent points out that “we review final agency actions, not preliminary complaints.” Partial Dissent at 933. That is true, of course, but not the issue here. Final agency action is usually a prerequisite to our review, but once an agency’s action is final and properly before us, we review the entire administrative record. See 5 U.S.C. § 706(2) (providing that a court “shall review the whole record” when determining whether an agency’s action was arbitrary or capricious); Camp v. Pitts, 411 U.S. 138, 142-43, 93 S.Ct. 1241, *92536 L.Ed.2d 106 (1973). An agency action need not stand or fall on the last document in the record; if the record as a whole satisfies the APA’s requirements, remand “would be pointless.” See Olivares v. TSA, 819 F.3d 454, 458-59 (D.C. Cir. 2016); Tourus Records, Inc. v. DEA, 259 F.3d 731, 738 (D.C. Cir. 2001). The Chenery rule against appellate courts’ post-hoc justification of agency action operates on the same principle. See SEC v. Chenery Corp., 318 U.S. 80, 87, 63 S.Ct. 454, 87 L.Ed. 626 (1943) (“The grounds upon which an administrative order must be judged are those upon which the record discloses that its action was based.” (emphasis added)); Tourus Records, 259 F.3d at 738. Any ambiguity that might exist in the Penalty Notice, taken in isolation, disappears on consideration of the record as a whole, and of the Prepenalty Notice in particular.

B

We have explained that an exporter may be found liable under section 560.204 if it ships goods from the United States to a third country, with reason to know that those goods are specifically intended for reexport to Iran, even if the goods never arrive in Iran. OFAC found that Epsilon made thirty-nine such shipments, in each case with the requisite reason to know. We now consider whether the agency’s determinations were arbitrary and capricious. This case turns on OFAC’s factual determination that Epsilon’s conduct contravened section 560.204, and so the central question in the arbitrary-and-capricious analysis is whether substantial evidence supported that determination. See Safe Extensions, Inc. v. FAA, 509 F.3d 593, 604 (D.C. Cir. 2007).

The APA’s substantial evidence standard “requires more than a scintilla, but can be satisfied by something less than a preponderance of the evidence.” Town of Barnstable v. FAA, 740 F.3d 681, 687 (D.C. Cir. 2014) (quoting Fla. Gas Transmission Co. v. FERC, 604 F.3d 636, 645 (D.C. Cir. 2010)). If that threshold is met, we must uphold the agency’s judgment regarding the relevant facts, even if we think the “evidence tends to weigh against the agency’s finding.” See United Steel Workers, 707 F.3d at 325. However, we cannot examine the agency’s proffered evidence in isolation; we must also consider “whatever in the record fairly detracts from its weight.” Town of Barnstable, 740 F.3d at 687 (quoting Universal Camera Corp. v. NLRB, 340 U.S. 474, 488, 71 S.Ct. 456, 95 L.Ed. 456 (1951)).

We begin our exploration of the facts on the parties’ common ground: Epsilon sent thirty-nine shipments of car accessories from the United States to Asra International, and those accessories arrived in Du-bái. The only disputed question, in light of our textual analysis above, is whether Epsilon knew, or had reason to know, that Asra International specifically intended to reexport those shipments to Iran. OFAC’s guidance explains that “reason to know” can be established “through a variety of circumstantial evidence,” including “course of dealing, general knowledge of the industry or customer preferences, working relationships between the parties, or other criteria far too numerous to enumerate.”8 Transshipments Guidance at 2. We consider the thirty-nine shipments in two groups: the thirty-four shipments sent between 2008 and 2011, and the five shipments sent in 2012. We conclude that OFAC’s findings regarding the first group (the 2008-2011 shipments) were adequately justified, but the agency’s findings regarding the latter group (the 2012 shipments) were not.

i

Record evidence tends to show that Asra International distributed exclusively *926in Iran as late as December 2011. Specifically, Asra International’s English-language website presented Asra International (“Dubai Asra”) as an affiliate of the Asra Electronic Trading Company of Tehran (“Tehran Asra”).9 The website’s “Contact Us” page, under the heading “Asra International Corporation L.L.C.,” listed only two addresses: one for Asra International Corporation in Dubai, United Arab Emirates, and one for Asra Electronic Trading Company in Tehran, Iran. The same website’s “About Us” page, again under the “Asra International Corporation” heading, announced that “Asra Trading Company revels in its 10 long years of experience on Iran’s car audio & video market,” having established “the broadest car audio & video systems distribution and sales network in Iran, supported by 150 of Iran’s most reputable sales agents in different cities.” A.A. 85. The marketing copy made several references to Asra’s success in “the country,” implying that the company served only a single country, Iran; indeed, no other countries were mentioned on this page. See id. Finally, the website’s “Dealers” tab displayed a long list of sales agents, all located in Iran. OFAC could reasonably infer from this website that Dubai Asra distributed only in Iran, by reexporting goods to Tehran Asra, which then transported those goods to dealers throughout the country.

Epsilon had reason to know these facts, which were available on Asra’s public, English-language website. There is also direct evidence that Epsilon had actual knowledge of Asra’s website and its contents. Specifically, Epsilon copied images found there to its own website, displaying them in a photo gallery labeled “Iran” as recently as 2012.10 Thus, in addition to demonstrating Epsilon’s awareness of Asra’s website, these photos suggest that Epsilon actually knew of Dubai Asra’s distribution in Iran. Further evidence that Epsilon knew of Dubai Asra and Tehran Asra’s connection came in the form of a 2008 freight manifest, recording a shipment from Epsilon’s address directly to Tehran Asra’s address.

Because nothing in the record suggests that Asra International made sales anywhere other than Iran before 2012, Epsilon focuses on rebutting the inference that Dubai Asra and Tehran Asra are affiliates. The company offers a letter from a Dubai Asra manager, alleging that Tehran Asra is a separate company that is solely responsible for thg website and pirated Dubai Asra’s trademarks,11 But the agency *927was under no obligation to consider this letter, which was not submitted to OFAC and was not part of the agency record. Epsilon offers no reason for not including the letter, which was dated May 16, 2014, in its response to the Prepenalty Notice, which the company submitted on June 6, 2014. See, e.g., CTS Corp. v. EPA, 759 F.3d 52, 64 (D.C. Ci