United States Court of Appeals

For the First Circuit

No. 21-1774

NICHOLAS L. TRIANTOS,

Plaintiff, Appellant,

v.

GUAETTA & BENSON, LLC; AUDREY G. BENSON; PETER V. GUAETTA; SARAH 

T. FITZPATRICK,

Defendants, Appellees,

DEUTSCHE BANK NATIONAL TRUST COMPANY, as Trustee for Morgan 

Stanley ABS Capital I Inc. Trust 2004-HE4, Mortgage Pass-Through 

Certificates, Series 2004-HE4; SELECT PORTFOLIO SERVICING, INC.; 

COUNTRYWIDE HOME LOANS, INC.; BANK OF AMERICA, N.A.; NEW CENTURY 

MORTGAGE CORPORATION,

Defendants.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. William G. Young, U.S. District Judge]

Before

Gelpí, Lynch, and Rikelman,

Circuit Judges. 

Nicholas L. Triantos, pro se.

John F. Gallant, with whom Nancy A. Morency and Gallant & 

Ervin, LLC were on brief, for appellees. 
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January 30, 2024
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RIKELMAN, Circuit Judge. After Deutsche Bank National 

Trust Company foreclosed on and sold his home, Nicholas Triantos 

sued various parties, including the law firm that represented the 

bank in the foreclosure sale and three of its individual partners. 

The district court dispensed with the suit on a motion to dismiss, 

and we affirmed. The law firm and its partners then moved for 

sanctions against Triantos under Federal Rule of Civil Procedure 

11. The district court granted the motion and ordered Triantos to 

pay $10,000 in attorneys' fees and $32.00 in costs. Because the 

court imposed sanctions under Rule 11 without following the rule's

procedural requirements, we reverse and vacate the order.

I. BACKGROUND

In 2014, several years after Triantos defaulted on his 

mortgage, Deutsche Bank conducted a foreclosure sale of his 

property. On February 17, 2017, Triantos filed suit in 

Massachusetts state court, alleging that Deutsche Bank had no 

authority to execute the sale because the mortgage had not been 

validly assigned to it. Along with various mortgage lenders and 

servicers, Triantos named Guaetta & Benson, LLC ("G&B"), the law 

firm that handled the foreclosure sale on Deutsche Bank's behalf, 

and three of its partners as defendants. 

Deutsche Bank removed the suit to federal court, where 

Triantos filed an amended complaint that contained eight causes of 

action under both state and federal law. G&B then moved to dismiss 
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the complaint for failure to state a claim under Federal Rule of 

Civil Procedure 12(b)(6), as did the other defendants. The 

district court granted the motions and dismissed the case on 

September 21, 2017. Triantos appealed. 

Two months later, G&B moved for sanctions against 

Triantos and his former state court lawyer, Michael McCardle. 

Although G&B filed separate motions under both Federal Rule of 

Civil Procedure 11 and its state law equivalent, the federal motion 

erroneously cited state procedural principles. The district court 

stayed these motions pending the outcome of the appeal on the 

merits. After we affirmed the district court's dismissal of the 

suit, G&B renewed its sanctions motions in 2020. 

On September 15, 2021, the district court held a hearing 

on the renewed motions, at which Triantos appeared pro se. His 

former lawyer, McCardle, against whom G&B also moved for sanctions, 

did not attend the hearing and indeed had never made any appearance 

in the federal action. See Triantos v. Guaetta & Benson, LLC, 52 

F.4th 440, 446 (1st Cir. 2022) ("Triantos I"). At the hearing, 

the court did not endeavor to determine whether Rule 11's 

procedural requirements had been met as to Triantos or McCardle. 

Instead, the court pressed Triantos to explain why his claims 

against G&B did not warrant sanctions. When Triantos attempted to 

explain why the claims in the complaint were sufficiently 

meritorious to escape sanctions, the court mistook his explanation 
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for an effort to relitigate the case and rejected the theory out 

of hand, suggesting that our decision to affirm the Rule 12(b)(6) 

dismissal foreclosed Triantos's argument. The court then entered 

a one-line docket entry granting $10,000 in attorneys' fees and 

$32.00 in costs as a sanction pursuant to Federal Rule 11. 

Triantos, again appearing pro se, now seeks review of this order.1

II. DISCUSSION

A. Rule 11

Rule 11(b) of the Federal Rules of Civil Procedure 

provides that, "[b]y presenting to the court a pleading, written 

motion, or other paper," an attorney or unrepresented party makes 

certain certifications. Fed. R. Civ. P. 11(b). For example, an 

attorney who files a complaint or motion warrants that "(1) it is 

not being presented for any improper purpose," and "(2) the claims, 

defenses, and other legal contentions [in the relevant filing] are 

warranted by existing law or by a nonfrivolous argument for 

extending, modifying, or reversing existing law or for

establishing new law." Fed. R. Civ. P. 11(b)(1)-(2). 

To enforce compliance with Rule 11(b), courts may impose 

sanctions on parties who violate it. See Fed. R. Civ. P. 11(c)(1) 

1 After Triantos appealed the sanctions order, the district 

court ordered him to pay a $15,000 bond to cover the costs of 

appeal. In its brief, G&B urged us to dismiss this appeal because 

Triantos had not yet paid the bond. Because Triantos subsequently 

paid the bond, however, we do not address this argument. 
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("If, after notice and a reasonable opportunity to respond, the 

court determines that Rule 11(b) has been violated, the court may 

impose an appropriate sanction on any attorney, law firm, or party 

that violated the rule or is responsible for the violation."). 

Sanctions may be initiated by the court or an opposing party's 

motion. Fed. R. Civ. P. 11(c)(2)-(3). Regardless of how the 

process starts, any "order imposing a sanction must describe the 

sanctioned conduct and explain the basis for the sanction." Fed. 

R. Civ. P. 11(c)(6) (emphasis added).

When a party moves for sanctions, it must follow certain

additional procedural requirements. The motion "must be made 

separately from any other," and it "must be served [on the 

offending attorney or unrepresented party] under [Federal Rule of 

Civil Procedure] 5, but it must not be filed or be presented to 

the court if the challenged paper, claim, defense, contention, or 

denial is withdrawn or appropriately corrected within 21 days after 

service or within another time the court sets." Fed. R. Civ. P. 

11(c)(2) (emphasis added). 

Together, these provisions provide a "safe harbor" for 

attorneys, law firms, or parties accused of sanctionable conduct

by their opponent. See Fed. R. Civ. P. 11 advisory committee's 

note to 1993 amendment. As the plain language of the rule 

indicates, these requirements are mandatory rather than suggested. 

"[T]he object of the safe harbor is to allow a party to privately 
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withdraw a questionable contention without fear that the 

withdrawal will be viewed by the court as an admission of a Rule 

11 violation." Young v. City of Providence ex rel. Napolitano, 

404 F.3d 33, 39 (1st Cir. 2005). Accordingly, "a party seeking 

sanctions must follow a two-step process" in every case. Ridder

v. City of Springfield, 109 F.3d 288, 294 (6th Cir. 1997). First, 

"[t]he party seeking sanctions must serve the Rule 11 motion on 

the opposing party at least twenty-one days before filing the 

motion with the district court, and [second,] sanctions may be 

sought only if the challenged pleading is not withdrawn or 

corrected within twenty-one days after service of the motion."

Brickwood Contractors, Inc. v. Datanet Eng'g, Inc., 369 F.3d 385, 

389 (4th Cir. 2004) (en banc) (emphasis added). 

Because an attorney or unrepresented party must have the 

opportunity to "withdraw or correct a challenged submission"

before their opponent can file a motion for sanctions with the 

court, the safe-harbor provisions necessarily limit when a party 

may move for sanctions. See In re Pennie & Edmonds LLP, 323 F.3d 

86, 89 (2d Cir. 2003). Of critical importance here, once a court 

has evaluated and ruled on the challenged filing, the attorney or 

unrepresented party can no longer withdraw it. For this reason, 

"a party cannot delay serving its Rule 11 motion until conclusion 

of the case (or judicial rejection of the offending contention)."

Fed. R. Civ. P. 11 advisory committee's note to 1993 amendment. 
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Indeed, courts have held that Rule 11 sanctions cannot be sought 

in the precise circumstances of this case: after the court has 

dismissed the complaint. See Barber v. Miller, 146 F.3d 707, 710-

11 (9th Cir. 1998); see also Ridder, 109 F.3d at 297 (holding that 

party "g[ave] up the opportunity to receive an award of Rule 11 

sanctions . . . by waiting to file the motion until after the entry 

of summary judgment"); Hunter v. Earthgrains Co. Bakery, 281 F.3d 

144, 152 (4th Cir. 2002) ("[T]he 'safe harbor' provisions of Rule

11(c)(1)(A) preclude the serving and filing of any Rule 11 motion 

after conclusion of the case.").

B. Reaching the Errors on Appeal

Before addressing the procedural errors below, we pause 

to explain our rationale for reaching them. The only discussion 

by the parties of the procedural defects was at oral argument 

before us and in Rule 28(j) letters filed shortly thereafter. 

Ordinarily, in this situation, we would consider Triantos's 

procedural objections to the sanctions order to be waived. See

Sparkle Hill, Inc. v. Interstate Mat Corp., 788 F.3d 25, 29-30

(1st Cir. 2015) (explaining that our "customary practice" is to

deem arguments not raised in a party's opening brief waived). 

However, we find that the particular circumstances of this case do 

not "require a robust application of waiver." Id. at 29.

To begin, we view Triantos, a transactional lawyer

without any litigation experience who is not a member of the 
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foreclosure bar, as functionally equivalent to a pro se litigant. 

And although "the right of self-representation is not 'a license 

not to comply with relevant rules of procedural and substantive 

law,'" Eagle Eye Fishing Corp. v. U.S. Dep't of Com., 20 F.3d 503, 

506 (1st Cir. 1994) (citation omitted), we "endeavor, within 

reasonable limits, to guard against the loss of pro se claims due 

to technical defects," Boivin v. Black, 225 F.3d 36, 43 (1st Cir. 

2000). Thus, we give Triantos some leeway in interpreting the 

scope of his arguments on appeal. 

Next, our ordinary concern about allowing a litigant to 

"[s]andbag[]" the opposing party by raising new arguments outside 

of its opening brief is simply not implicated here. Sparkle Hill, 

788 F.3d at 29. After Triantos raised his procedural objections 

at oral argument, he offered to submit a 28(j) letter on the issue. 

In its responsive 28(j) letter, G&B argued that it had complied

with Rule 11's procedural requirements, although it did not cite 

any federal law supporting its position. Thus, G&B was not 

"deprive[d] . . . of an opportunity to respond in writing on the 

issue." See id.

Finally, we note that Triantos's recognition of the

procedural errors was likely made possible by our decision in 

Triantos I, 52 F.4th 440, reversing the sanctions order against 

McCardle on procedural grounds. In the district court, G&B's 

motion for sanctions erroneously cited Massachusetts procedural 
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law, which may have started the entire process off on the wrong 

foot.2 Moreover, the district court did not mention Rule 11's 

procedural requirements at any point during the motion hearing or 

in its sanctions order. This is therefore not a case where 

Triantos's opening brief on appeal failed to "challeng[e] express 

grounds upon which the district court prominently relied in 

entering judgment." Sparkle Hill, 788 F.3d at 30. Instead,

neither G&B nor the district court recognized or grappled with 

Rule 11's procedural requirements at any point in this litigation. 

Under these unique circumstances, we find that Triantos did not 

waive his procedural arguments by failing to raise them in his 

opening brief.

C. Plain Error Review

Although Triantos did not waive his procedural arguments

on appeal, we must nonetheless consider the effect of his failure 

to raise such arguments in opposition to G&B's sanctions motion 

below. When a party fails to raise an argument to the district 

court, we consider that argument forfeited and review only for

plain error. See Diaz-Seijo v. Fajardo-Vélez, 397 F.3d 53, 55 

(1st Cir. 2005). Although plain error is a demanding hurdle rarely 

2 In fact, based on state law, G&B suggested that a party may

move for sanctions under Rule 11 only "[o]nce a defendant 

establishes that a complaint lacks merit and obtains summary 

judgment or dismissal of an action." As we explained above, the 

precise opposite is true: Once an action is dismissed, a party may 

no longer move for sanctions under Rule 11. 
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cleared in civil cases, see Sparkle Hill, 788 F.3d at 30, we 

conclude that this is the unusual case in which reversing and 

vacating is warranted under this standard.3 

To prevail on plain error review, a litigant must show 

that "(1) an error occurred (2) which was clear or obvious and 

which not only (3) affected the [appellant's] substantial rights, 

but also (4) seriously impaired the fairness, integrity or public 

reputation of the judicial proceedings." Id. (citation omitted). 

This case easily satisfies the first two criteria because Rule 11

imposes mandatory procedural requirements that must be met before 

a party may move for sanctions and before a district court may

impose any sanctions; none of those requirements was met here. It 

also satisfies the third criterion. An error affects a party's 

substantial rights if it "affected the outcome of the district

court proceedings." United States v. Olano, 507 U.S. 725, 734 

(1993). The procedural errors affected Triantos's substantial 

3 Further, our decision here is not inconsistent with Nyer v. 

Winterthur International, 290 F.3d 456 (1st Cir. 2002). In Nyer,

we upheld a well-reasoned sanctions order against plaintiffs' lead 

trial counsel after declining to consider his belatedly raised 

arguments based on Rule 11's safe-harbor requirements. Id. at 

460-62. In that case, like here, Nyer had failed to raise his

safe-harbor argument to the district court. Id. at 460. We 

concluded that no "excusatory circumstances" were present and thus 

declined to review Nyer's new arguments under any standard on 

appeal. Id. (quoting Corrada Betances v. Sea-Land Serv., Inc., 

248 F.3d 40, 44 (1st Cir. 2001)). By contrast, for the reasons we 

have explained, the facts here do present "excusatory 

circumstances" justifying plain error review of Triantos's 

procedural arguments. 
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rights here "because [he] was subjected to Rule 11 sanctions that 

the district court was not empowered to impose." Brickwood, 369 

F.3d at 396. 

As for the fourth criterion, we conclude that the 

"interests of justice would best be served" by remedying the 

procedural failures in this case, in part because leaving the 

district court's errors uncorrected would frustrate the "important 

goals" embodied in Rule 11. Id. at 398-99. The 1993 amendments 

to Rule 11, which introduced the safe-harbor provisions, were 

intended to "reduce Rule 11's volume, formalize appropriate due 

process considerations of sanctions litigation, and diminish the 

rule's chilling effect." Ridder, 109 F.3d at 294; see also

Brickwood, 369 F.3d at 397. Allowing the sanctions order against 

Triantos to stand when G&B did not even "attempt to comply with 

the requirements of the safe-harbor provisions," and the district 

court did not cite or grapple with these requirements, would 

undermine these objectives. Brickwood, 369 F.3d at 398. Further, 

Triantos's pro se status, combined with the district court's and 

G&B's inattention to Rule 11's procedural requirements, leads us 

to conclude that it would "be unjust for [Triantos] to bear the 

full weight of the consequences of an unfamiliarity shared by all 

involved." Id. Thus, although Triantos forfeited his procedural 
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arguments by failing to raise them to the district court, we turn 

to them now and reverse based on plain error.4

D. Procedural Errors Below

We conclude that a string of procedural errors, both by 

G&B and the district court, require reversing the sanctions order 

here. First, G&B served its motion on Triantos only after the 

district court had dismissed the case. That is simply too late 

under Rule 11 because, by that point, Triantos could no longer 

withdraw the objectionable complaint. By waiting to serve its 

sanctions motion until the district court had resolved the case, 

G&B "g[ave] up the opportunity to receive Rule 11 sanctions." 

Ridder, 109 F.3d at 297.

Second, regardless of the first error, G&B also failed 

to comply with Rule 11's safe-harbor requirements. Despite G&B's 

representations to the contrary at oral argument before us, the 

record makes clear that G&B did not serve the motion for sanctions 

upon Triantos at least twenty-one days prior to filing it with the 

district court. Instead, G&B filed the motion on the docket and 

merely certified that Triantos "[was] being served under the 

4 We emphasize that our decision today, based on the unique 

facts here and the mandatory procedural requirements of Rule 11,

should not be interpreted as carte blanche for pro se parties to 

abdicate their responsibility to properly preserve arguments by 

raising them in the first instance to the district court and then 

arguing those issues in their opening brief before us. And we 

trust that our opinion will be helpful in highlighting for all 

parties the mandatory nature of Rule 11's procedural requirements. 
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Court's ECF Certificate of Service filing system." This 

certification, of course, does not suffice to satisfy Rule 11. 

Under the rule, G&B was required to serve its motion upon Triantos

at least three weeks before it filed it with the court, not at the 

same time. G&B also attached a letter to its motion in which it 

had advised Triantos and McCardle that it planned to pursue 

sanctions if Triantos did not withdraw the complaint. But this 

letter could not have triggered the safe-harbor period. As we

already explained when we rejected this exact same argument in our 

decision reversing the sanctions order against McCardle, "informal 

notice is not a substitute" for service of the actual motion. 

Triantos I, 52 F.4th at 447.

Rule 11 "sets forth inflexible rules governing the 

circumstances under which Rule 11 sanctions may be sought and 

granted." Brickwood, 369 F.3d at 394; see also Lamboy-Ortiz v. 

Ortiz-Vélez, 630 F.3d 228, 244-45 (1st Cir. 2010) (reversing 

sanctions order because the moving party's failure to comply with 

Rule 11's mandatory requirements "disqualif[ied] Rule 11 as a 

basis" for the district court's decision). The district court

therefore committed reversible procedural error by granting G&B's

motion despite G&B's failure to comply with the rule's 

requirements.

Finally, the district court overlooked its own Rule 11 

duties. The district court's sanctions order consisted of a 
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one-line docket entry "awarding attorneys' fees in the amount of 

$10,000 and fees in the amount of $32.00." This order does not 

"describe the sanctioned conduct and explain the basis for the 

sanction," as is required by the rule's clear mandate. Fed. R. 

Civ. P. 11(c)(6). Such deficiencies make it difficult for us to 

conduct meaningful appellate review. G&B's underlying motion 

advanced various theories for why Triantos should be sanctioned

keyed to different counts in the complaint. Without an adequate 

explanation from the district court, we cannot discern which of 

Triantos's causes of action it found sanctionable or why.

At oral argument, G&B suggested that we can and should

infer the district court's reasoning from the totality of the

record, including the complaint and the court's comments at the 

motion hearing. We decline to do so for two reasons. First, we

are required to interpret Rule 11 according to its plain meaning, 

see Cooter & Gell v. Hartmarx Corp., 496 U.S. 384, 391 (1990), and 

subsection (c)(6) explicitly requires that any sanctions order 

imposed under Rule 11 include a description of the offending 

conduct and an explanation for the sanction. Fed. R. Civ. P. 

11(c)(6). Second, this procedural requirement serves the 

important purposes of "promot[ing] the rational exercise of trial 

court discretion in the utilization of Rule 11 

and . . . facilitat[ing] effective appellate review." 5A Charles 

Alan Wright & Arthur R. Miller, Federal Practice & Procedure
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§ 1337.3 (4th ed. 2023). Thus, we will not "comb through the 

accusing parties' pleadings and briefs filed in the district court 

and the transcript of . . . oral argument . . . in order to 

locate . . . facts that might constitute sufficient grounds for 

the imposition of Rule 11 sanctions." Shirvell v. Gordon, 602 F. 

App'x 601, 606 (6th Cir. 2015) (first and second alterations in 

original) (quoting Elsman v. Standard Fed. Bank, 46 F. App'x 792, 

801 (6th Cir. 2002)). Instead, the onus falls upon the party 

moving for sanctions, and the district court, to ensure that any 

sanctions order adequately explains its basis. 

III. CONCLUSION

The district court plainly erred by granting G&B's

sanctions motion when (1) G&B served its motion on Triantos long 

after the district court already had dismissed the offending 

complaint, and (2) in any event, G&B had not met its obligation 

under Rule 11's safe-harbor provisions to serve the motion on

Triantos twenty-one days prior to filing it with the court. The 

district court also erred by imposing sanctions without describing 

in its order the sanctionable conduct or explaining the basis for 

its decision. 

Accordingly, we reverse and vacate the order.