Cеcilia Nichols appeals from the February 27, 2004 decision and order of the United States District Court for the Southern District of New York (Victor Marrero, J.) dismissing without prejudice her claims of wrongful termination of disability benefits under the Employee Retirement Income Security Act of 1974, as amended and codified at 29 U.S.C. §§ 1001 — 1461 and scattered sections of 26 U.S.C. (“ERISA”). The district court held that while defendant-appellee The Prudential Insurance Company of America (“Pruden *101 tial”) did violate the deadlines for completing review of a denial of benefits set forth in 29 C.F.R. § 2560.503-1(h), 1 promulgated pursuant to ERISA, it made good faith efforts to complete this review that placed it in substantial compliance with the regulation. The district court therefore dismissed Nichols’s claims for failure to exhaust administrative remedies, but ordered that Prudential complete its review and render a decision within thirty days of the date that Nichols complies with Prudential’s requests for additional information and for an independent medical examination. On appeal, Nichols argues that the “substantial compliance” doctrine is inconsistent with the regulation, that Prudential did not technically or substantially comply with the regulation, and that in the absenсe of a decision by Prudential, the district court should have reviewed the denial of benefits de novo. Prudential argues that the district court’s order was an interlocutory remand order over which this Court does not have appellate jurisdiction, that the “substantial compliance” doctrine is proper and consistent with the tolling scheme implemented by the current version of the regulation, and that any district court review of the denial of benefits should be under an arbitrary and capricious standard. We hold that the district court’s dismissal without prejudice is a final decision over which this Court has aрpellate jurisdiction. We further hold that. the plain language of 29 C.F.R. § 2560.503-1(h) precludes the judicial creation of a “substantial compliance” doctrine. We finally hold that the lack, of discretion vested in the plan administrator, or alternatively, failure to exercise any such discretion, requires de novo review of the denial of benefits. We therefore va-eate the district court’s order and remand to the district court for de novo review of the merits of Nichols’s claim.
BACKGROUND
While the facts pertaining to the underlying merits of Nichols’s claim are disputed, the facts concerning the coursе of communications between Nichols and Prudential at issue here are not. We review and summarize here only this undisputed factual background.
Cecilia Nichols participated in a group insurance plan (the “plan”) offering short— and long-term disability coverage, underwritten and administered by Prudential. The plan offered long-term disability coverage, and limited coverage to twenty-four months for disabilities based in part on mental disorders.
In November 1999, Nichols submitted a cláim based on several diagnosed medical conditions that resulted in pain, fatigue, weakness,' nausea, dizziness, depression, аnd disorientation. As per the terms of the plan, Prudential paid short-term disability benefits until April 29, 2000, and then began paying long-term benefits. On December 12, 2001, Prudential notified Nichols by letter that her benefits would be suspended after April 29, 2002, because she was no longer totally disabled and her disability was based in part on a mental disorder. On December 18, 2001, Prudential called Nichols by telephone and informed her of the termination of benefits and the right to appeal, and told Nichols that she should forward medical evidence of continued disability if she did s appeal. Nichols called Prudential on December 19, 2001, disсussed the appeals process and *102 the medical evidence necessary, and was informed that if she appealed, Prudential would assess the need for an independent medical evaluation (“IME”) at that time.
Nichols filed a written appeal with Prudential by letter dated April 11, 2002 (day 0) 2 . No further correspondence was exchanged until June 17 (day 67), when Prudential acknowledged receipt of Nichols’s letter, stated that Prudential was performing a review, and stated that Nichols would be contacted within 30 days with a decision or the status of the evaluation. On July 1 (day 81), Prudential requested by telephone that Nichols submit to an IME. A week later, on July 8 (day 88), Nichols informed Prudential by telephone that she refused any IME and would consult with an attorney. Nichols then sent a letter, through counsel, on July 11 (day 91), referring to Nichols’s appeal as an ERISA matter and instructing Prudential not to delay or disturb resolution of the appeal. On July 25 (day 105), Prudential responded by letter, stating that it could not resolye Nichols’s appeal until she submitted medical records of her continuing treatment. Nichols wrote a final letter on August 9 (day 120), rejecting Prudential’s July 25 letter, and referring specifically to 29 C.F.R. § 2560.503-l(h) as requiring timely processing of Nichols’s appeal.
On October 25, 2002 (day 197), Nichols filed the present suit. Nichols wrote to Prudential on November 7, 2002, notifying Prudential of the suit and stating that no further claims proceedings, such as an IME, were appropriate. Prudential responded by reminding Nichols to attend her scheduled IME by letter dated November 4, 2002. Prudential subsequently moved to dismiss without prejudice for failure to exhaust administrative remedies.
Nichols v. Prudential Ins. Co. of Am.,
The district court held that “while Prudential technically did not comply with the letter of the regulation, Nichols ignored its spirit,” and dismissed Nichols’s complaint without prejudice “to allow Prudential to complete its reviеw of her claim.”
Id.
The district court observed that 29 C.F.R. § 2560.503-1(h) “ordinarily” set a 60-day deadline for appeals of a denial of benefits, which could be extended to 120 days for “special circumstances,” provided a written notice to the claimant preceded such extension.
Nichols,
*103 This appeal followed. Nichols argues that this Court should reject the substantial compliance doctrine; that in any case Prudential’s actions do not constitute substantial compliance; and that on remand, the district court should conduct a de novo review оf the administrative record. Prudential argues that the district court’s order is an interlocutory order remanding to Prudential as the plan administrator, over which this Court has no appellate jurisdiction; that Prudential was in fact in technical compliance with the regulatory deadlines; and that this Court should adopt the substantial compliance doctrine and find Prudential substantially complied with the regulatory deadlines.
DISCUSSION
I. Appellate Jurisdiction
We first address the issue of our jurisdiction over this appeal. Prudential correctly notes that only final decisions of the district court are appealable as of right under 28 U.S.C. § 1291. “Federal appellate jurisdiction generally depends on the existence of a decision by the District Court that ends the litigation on the merits and leaves nothing for the court to do but execute the judgment.”
Coopers & Lybrand v. Livesay,
Prudential argues that the district court’s order at issue here is a remand to the ERISA plan administrator, and that our jurisdiction over such a remand is undecided by this Court.
See generally Zervos v. Verizon N.Y., Inc.,
At this time, we need not decide with which circuits we agree. The district court’s order under review here does not use the term “remand,” and substantively differs from a remand order of the type considered in the above cases. Each of the above-cited cases involved a remand to the plan administrator for a new determination, and, where necessary, vacatur of the previous determination.
Hensley v. Northwest Permanente P.C. Ret. Plan & Trust,
No. 96 Civ. 1166,
The district court order at issue here is quite different. By its own terms, it is a dismissal without prejudice, not a vacatur and remand. Indeed, the primary thrust of the decision is that Prudential in fact made no error that now needs to be corrected, and that Nichols precluded a determination by bringing suit prematurely.
See Nichols,
We therefore consider the district court’s order to be a dismissal without prejudice, not a remand. It is well established that a dismissal without prejudice, absent some retention of jurisdiction such as an invitation to amend the complaint, terminates the action and is a final decision from which an apрeal lies.
Wynder v. McMahon,
We hold that the specific district court decision at issue here is a dismissal without prejudice, that it is a final decision, and that appeal lies as of right to this Court under 28 U.S.C. § 1291. Accordingly, we turn now to the substance of the appeal.
II. The Regulatory Deadlines
There are two basic substantive questions in this appeal. The first, which we address in this section, concerns Prudential’s compliance with the regulatory deadlines. If Prudential missed these deadlines, then Nichols’s claim is deemed denied and her administrative remedies are therefore exhausted, removing any procedural obstacle to the present suit. Prudential argues both that it has complied technically with the deadlines, and that we should recognize a substantial compliance exception to the deadlines and hold that Prudential substantially complied with the deadlines. We first address the standard of review by whiсh we review the district court’s conclusions as to these issues, and then consider each argument in turn. The second question, *105 which is addressed in section III, concerns the standard of review that a district court should use in reviewing a claim that has been deemed denied after the failure of the plan administrator to meet the regulatory deadlines. Under ERISA, a district court reviews a plan administrator’s discretionary decision under an arbitrary and capricious standard and all- other administrator decisions de novo. The question of which standard of review the district court should apply turns on whether the plan instrument vests the plan administrator with discretion in the administrator’s treatment of claims, and whether the administrator’s action in missing the deadlines is a valid exercise of that discretion.
A Standard of Our Review of the District Court’s Decision
We first address the standard by which we review the district court’s judgment. This Court has never explicitly stated the standard of review for a district court’s dismissal of an ERISA claim for failure to exhaust administrative remedies. It is similarly unclear whether such a motion is properly brought for failure to state a claim, lack of subject matter jurisdiction, or on some other procedural basis.
See Kennedy v. Empire Blue Cross & Blue Shield,
B. Technical Compliance
The question of whether Nichols exhausted administrative remedies is in turn dependent on whether Prudential complied with the regulatory deadlines of 29 C.F.R. § 2560.503-1(h). This regulation requires that a plan administrator’s decision reviewing a denial of benefits must ordinarily be made within 60 days of the request for such review, but may be made within 120 days for special circumstances. 29 C.F.R. § 2560.503-1(h)(1)(i). Notice of any such extension must be given in writing before the commencement of the extension. 29 C.F.R. § 2560.503-1(h)(2). If no decision is rendered by the deadline, the claim for benefits is deemed denied on review. 29 C.F.R. § 2560.503-1(h)(4). Thus, if Prudential failed to meet the deadlines, Nichols’s administrative appeal is deemed denied, and her administrative remedies are therefore exhausted.
In the present case, Prudential first communicated with Nichols about her appeal- 67 days after the date of her letter requesting the appeal. It first expressed the need for an IME on day 81, and stated that it could not proceed without the IME and further medical records on day 105. As of the commencement of the present *106 suit on day 197, Prudential had never rendered a formal decision on Nichols’s claim.
Prudential argues on appeal, though it did not do so below, that despite these time frames, it complied with the letter of the regulation. It points out while the record reflects that Nichols’s original request for review was dated April 11, there is no record evidence of when the letter was mailed or received, and that use of standard mailing delays and weekend extensions brings its day-67 letter within the 60-day deadline. We are not required to consider this argument,
see Sniado v. Bank Austria AG,
C. Substantial Compliance
The question, then, is whether Prudential’s failure to comply with the lettеr of the regulatory deadlines may be excused by its good-faith efforts to resolve the appeal subsequent to the expiration of the deadline. We observe at the outset that the language of the regulation is not ambiguous. It states explicitly that failure to meet the 60-day deadline (or 120 days under “special circumstances” and after notice of such an extension) results in the claim being “deemed denied.” 29 C.F.R. § 2560.503-1(h)(4). The Supreme Court has also explained this regulation as stating “that a claim may be treated as having been denied after the 60- or 120-day period has elapsed,” which “enables a claimant to bring a civil action to have the merits of his application determined.”
Massachusetts Mut. Life Ins. Co. v. Russell,
In contrast, the district court relied on a Tenth Circuit case,
Gilbertson v. Allied Signal, Inc.,
Turning to the district court cases cited by the decision below and Prudential, we note that two of these cases, like
Gilbertson,
stand only for the propositiоn that a plan administrator who 1) substantially complied with the deadlines and 2) eventually exercised its discretion to deny benefits by the time of suit, should not be penalized by automatic reversal of the administrator’s decision or withholding of judicial deference.
See DiCamillo v. Liberty Life Assurance Co.,
It is true that many of our sister courts of appeal, in considering other requirements of Section 2560.503-1, in particular the notice of reasons for a denial and the right to appeal, have held that a plan administrator’s decision made in substantial compliance with the regulation can be upheld.
E.g., Heller v. Fortis Benefits Ins. Co.,
*108 On a final note, Prudential, on appeal, attempts to recast the substantial compliance issue as one of equitable tolling. Prudential argues that because Nichols has thwarted Prudential’s attempts to gather needed medical evidence, the regulatory deadline should be tolled for the period of this delay. It further argues that Section 2560.503-1 has been amended since the time period at issue here to include just such a tolling provision. Claims Procedure, 65 Fed.Reg. 70,246, 70,270 (Nov. 21, 2000) (codified at 29 C.F.R. § 2560.503-1(i)(4) (2004)). The amendment of the regulation may well indicate the Secretary of Labor’s understanding that the earlier version of the regulation applicable here did not incorporate such tolling. But we need not decide this issue, as equitable tolling will not place Prudential in compliance with the deadlines. The deadline expired on day 60 (or a few days after, if we were to accept Prudential’s mailing time argument), Prudential first requested an IME as part of the appeals process on day 81, and Nichols refused the IME on day 88. A tolling period cannot delay the expiration of a deadline when that deadline has already expired.
III. Standard of District Court Review of the Plan Administrator’s Decision
Nichols finally argues that’ on remand, the district court should review Prudential’s benefit determination de novo.
3
We review a plan administrator’s decision dе novo unless the plan vests the administrator with “discretionary authority to determine eligibility for benefits or to construe the terms of the plan,” in which case we use an “abuse of discretion” standard.
Firestone Tire & Rubber Co. v. Bruch,
We agree on both counts. A reservation of discretion need not actually use the words “discretion” or “deference” to be effective, but it must be clear.
Kinstler v. First Reliance Standard Life Ins. Co.,
A similar analysis applies here. The plan states that a disability “exists when Prudential determines that all of these conditions are met” and then goes on to list specific conditions. The plan also states that Prudential will pay benefits
*109
“when Prudential receives written proof of the loss.” The latter language is clearly objective. The phrase “when Prudential determines” is more troubling, but ultimately lacks sufficient indicia of subjectivity as required by
Kinstler. See O’Sullivan v. Prudential Ins. Co. of Am.,
No. 00 Civ. 7915,
Alternatively, even if Prudential was vested with discretion, it made no valid exercise of that discretion here. Our sister courts of appeal have again split on the question of whether a “deemed denied” claim is always entitled to de novo review. A majority of circuits have held thаt, absent substantial compliance with the deadlines, de novo review applies on the grounds that inaction is not a valid exercise of discretion and leaves the court without any decision or application of expertise to which to defer.
Jebian,
We agree with .the majority view.
Firestone
derived its holding from principles of trust law that “make a deferential standard of review appropriate when a trustee exercises discretionary powers.”
We note that
Jebian
and
Gilbertson
further hold that arbitrary and capricious review might still be appropriate if the plan administrator substantially complied with the deadlines.
Jebian,
CONCLUSION
For the foregoing reasons, the judgment of the district court is vacated, and the case is remanded for de novo review of Nichols’s entitlement to benefits under the plan.
Notes
. 29 C.F.R. § 2560.503-1 was significantly amended in 2000, Claims Procedure, 65 Fed.Reg. 70,246, 70,265-71 (Nov. 21, 2000), and slightly amended further in 2001, Claims Procedure, 66 Fed.Reg. 35,886, 35,888 (July 9, 2001). All references to the regulation in this opinion are to the 1999 version, unless otherwise specified.
. For convenience, relevant dates are parenthetically identified by the number of days since April 11, 2002. These identifications do not in themselves represent any legal conclusions, and do not incorporate any alterations to the counting method for weekends, holidays, equitable tolling, or other legal considerations. They are instead simple mathematical calculations included for convenience.
. In the proceedings below, Nichols first conceded the use of an arbitrary and capricious standard, and then withdrew that concession. To the extent that it is arguable that this issue is raised for the first time on appeal, we still have discretion to consider the issue if we are faced with a pure question, of law.
Sniado,
. Indeed, the recent amendment of the regulations, to include a tolling provision for an claimant's failure to cooperate, no doubt reflects such reasons.