The United States District Court for the District of Massachusetts recently addressed whether a “Designated Ongoing Operations” exclusion in a commercial general liability policy applied to coverage for damage to an aircraft operated by a third party. In Vineyard Aircraft Hangars Inc. v. New Hampshire Insurance Co., 2026 WL 972978 (D. Mass. Apr. 10, 2026), a federal district judge ruled that it did not, granting summary judgment to an insured on its declaratory judgment and breach of contract claims, while denying relief under Massachusetts General Laws Chapter 93A.

The underlying action alleged that an aircraft sustained damage after encountering a pothole or sinkhole while taxiing from an apron associated with Vineyard Aircraft Hangars (“VAH”). The aircraft was operated by a third party. The complaint alleged that VAH negligently constructed, maintained, and operated the apron and failed to comply with applicable standards governing airport property. It also alleged breach of an agreement to provide storage and parking. VAH tendered the claim to its insurer, which denied coverage.

VAH filed suit seeking a declaration of coverage, damages for breach of contract, and relief under state statutory law. The parties filed cross-motions for summary judgment.

The dispute focused on a “Designated Ongoing Operations” exclusion: “‘bodily injury’ or ‘property damage’ arising out of [Aircraft and/or Fueling Operations], regardless of whether such operations are conducted by you or on your behalf or whether the operations are conducted for yourself or for others.”

The insurer argued that the exclusion applied to all aircraft-related operations, without regard to who performed them. VAH contended that the exclusion applied only to operations conducted by the insured or on its behalf.

The court found the language ambiguous, noting that multiple courts also had found this language ambiguous when read in isolation. The Massachusetts court then looked to the reasoning in Emanuel v. Ace American Insurance Co., a decision issued by a federal court in Maryland in 2012. The Emanuel court explained the ambiguity inherent in the phrase “regardless of whether.”—

The ambiguity is inherent in the “regardless of whether” linguistic construction. If a friend were to say, “The party will be held tomorrow, regardless of whether it rains,” one would understand that “whether” is followed by a silent, implied “or not.” The statement means that the party will go forward, rain or shine—” whether or not it rains.”

But, ambiguity develops whenever a speaker states that something will occur “regardless of whether” two expressly stated alternatives occur. For example, if a friend says, “I will go to the party, regardless of whether Joe or Steve asks me,” she might mean that she will attend the party with one of two possible companions: Joe or Steve. But, she might mean, instead, that it does not matter if Joe asks her, if Steve asks her, or if neither of them asks her—she will attend the party in any event.

Because two alternatives are expressly presented, it is ambiguous whether the speaker’s use of “regardless of whether” is intended to differentiate between the two expressly presented alternatives or, instead, whether the speaker intends to differentiate between two express possibilities on the one hand, and the silent, implied possibility of “neither” on the other hand.

Given this reasoning, the Vineyard Aircraft Hangars, Inc. court concluded that the ambiguity was not resolved by the surrounding policy language. It also rejected the argument that one interpretation should be preferred to avoid redundancy with other exclusions, noting that both interpretations created some overlap.

The court then applied the standard allocation of burdens. The insured bore the initial burden of showing that a claim fell within the policy’s grant of coverage, and if that burden was met, the insurer must establish that an exclusion applies. The parties in Vineyard Aircraft Hangars, Inc. did not dispute that the claim fell within the coverage grant. The issue, therefore, was whether the exclusion applied. Additionally, under Massachusetts law, ambiguous policy language is construed against the insurer, and exclusions are interpreted narrowly. Applying those principles, the court adopted the insured’s interpretation. It read the endorsement to apply only to operations conducted by the insured or on its behalf. Because the underlying incident involved a third-party operator, the exclusion did not apply. The insurer, therefore, owed a duty to defend and indemnify.

The breach of contract claim followed from that conclusion. The policy imposed a duty to defend. The insurer denied that duty. Because coverage was found to exist, the denial constituted a breach. Consequently, the court held that the insurer was responsible for defense costs incurred in the underlying action as well as for attorney’s fees incurred in establishing the duty to defend.

The court reached a different result on the Chapter 93A claim. It concluded that the insurer’s position, although incorrect, reflected a legitimate dispute over policy interpretation and did not rise to the level required for liability under the statute.

In all, the exclusion at issue is not unusual. Language framed in terms of “regardless of whether” appears in many policies, including those issued to aviation-related businesses. But the Vineyard Aircraft Hangers, Inc. reflects that, when paired with multiple alternatives, that phrasing may support more than one reasonable reading. Where that occurs, and the ambiguity bears on an exclusion, Massachusetts law directs that the ambiguity be resolved in favor of the insured.

The case also illustrates the consequences that follow from a denial of the duty to defend. The insurer’s position here was not found to violate Chapter 93A, but it nonetheless resulted in liability for defense costs and fees. Vineyard Aircraft Hangers, Inc. demonstrates that where coverage depends on the interpretation of policy wording of this kind, the scope of the duty to defend, and the risks associated with denying are considerable.

About Timothy M. Ravich

Timothy M. Ravich concentrates his practice in the areas of aviation, product, and general civil litigation. Recognized as one of only 50 lawyers qualified as a Board-Certified Expert in the area of aviation law, Tim specializes in transactional and regulatory matters related to the ownership, maintenance, and utilization of aircraft, airports, and airspace. Click here to read Tim’s full attorney biography.