Advocacy in Action: Strategic Recovery After Major Revenue Loss

Following a post-closing contract loss, Castle Harbour led a strategic RWI claims process that secured over $8 million for a private equity client in under six months.

…

Castle Harbour was engaged by a private equity client to place RWI for its acquisition of a technology services company. Following closing, the target’s largest customer—representing over 20% of revenue—unexpectedly terminated its contract. Although the seller had represented that customer relationships were stable, a post-closing review revealed that the seller had prior knowledge of the customer’s dissatisfaction and desire to terminate its relationship, constituting a breach of the material customer representation.

Castle Harbour immediately helped the client prepare a detailed notice of claim, aligning the narrative precisely with policy language, and assisted in gathering supporting evidence of both the customer loss and the seller’s awareness. We also proactively engaged the insurer early and positioned the claim strategically to encourage a favorable outcome, maintaining active dialogue throughout to avoid delays. As a result of Castle Harbour’s strategic claims management, the insurer promptly acknowledged coverage, and the client received a material payment exceeding $8 million—covering losses tied to the canceled contract. The matter was resolved within approximately six months of the initial notice, a significantly faster timeline than is typical for RWI claims, and with a highly favorable result that minimized the financial impact to the client.

Preserving Value: Overcoming Customer Retention Risk Through Adept Advocacy

Castle Harbour secured full RWI coverage for a financial sponsor despite a missing contract renewal with the target’s largest customer.

…

Castle Harbour was engaged by a financial sponsor acquiring a business services company. A significant challenge emerged during diligence when it was discovered that the target’s largest U.S. contract lacked a fully executed renewal, raising concerns about customer retention generally and revenue stability post-closing.

Leveraging its experience in complex customer risk scenarios, Castle Harbour worked closely with the client and deal counsel to create a tailored diligence strategy designed to assuage underwriter concern and avoid an exclusion. By gathering targeted supplemental evidence of the customer relationship at issue, Castle Harbour engaged in effective advocacy with the RWI underwriters to provide full coverage for customer contracts without the need for any exclusion. This strategic advocacy preserved coverage for a material portion of the target’s enterprise value and enabled the buyer to proceed with confidence, maintaining deal terms without the need for renegotiation.

Policy type: Buyer-side RWI
Size: $500MM - $1B
Sector: Business Services

Buyer type: Financial Sponsor
Buyer jurisdiction: U.S.
Seller jurisdiction: U.S.

Strategic Advocacy: Overcoming Compliance Risks in a High-Stakes Acquisition

Castle Harbour helped a U.S. healthcare buyer secure broad RWI coverage in the face of a complex regulatory compliance issue involving a European medical device target.

…

Castle Harbour was engaged by a U.S.-based healthcare company pursuing the acquisition of a European medical device manufacturer with operations across Switzerland and Germany. A major diligence hurdle emerged when the target disclosed an unresolved regulatory compliance issue related to clinical trial documentation—a risk that threatened to trigger future product liability claims and regulatory sanctions.

Recognizing the sensitivity and complexity of the exposure, Castle Harbour worked hand-in-hand with the client’s regulatory counsel to frame the issue appropriately for the insurance markets. By carefully isolating the nature of the exposure and demonstrating proactive remediation efforts by the target, Castle Harbour successfully negotiated extremely limited, rather than broad, exclusions with the RWI underwriters.  The result: the buyer obtained comprehensive policy coverage for the balance of the target’s operations, mitigating the most critical regulatory risk and maintaining full acquisition momentum despite late-stage diligence concerns.

Policy type: Buyer-side RWI
Size: $250MM - $500MM
Sector: Healthcare / Life Sciences

Buyer type: Strategic / Corporate
Buyer jurisdiction: U.S.
Seller jurisdiction: Switzerland

Overcoming Jurisdictional Hurdles to Deliver Seamless RWI Coverage

Castle Harbour enabled a strategic buyer to secure RWI coverage on a Dutch-law-governed acquisition by restructuring the deal to align with U.S. disclosure standards.

…

Castle Harbour was engaged by a strategic buyer pursuing the acquisition of a cutting-edge technology and manufacturing company in The Netherlands. Despite the transaction being governed by Dutch law and structured under a European-style purchase agreement, Castle Harbour successfully secured an RWI policy—an uncommon feat in this context. 

Working in close coordination with the client and both U.S. and Dutch legal counsel, Castle Harbour led a strategic restructuring of the agreement to incorporate a U.S.-style disclosure framework acceptable to the RWI underwriter. This restructuring was essential to unlocking the broader protection offered by RWI, as compared to traditional European W&I policies. 

Leveraging its deep cross-border expertise and drawing on its significant M&A advocacy, Castle Harbour overcame initial skepticism from opposing counsel, who believed RWI was not viable under Dutch law. The result: a seamless insurance solution that enhanced deal certainty and protection for the buyer, on terms it was used to seeing in U.S.-based acquisitions.

Policy type: Buyer-side RWI
Size: $250MM - $500MM
Sector: Industrials

Buyer type: Strategic / Corporate
Buyer jurisdiction: U.S.
Seller jurisdiction: The Netherlands

Safeguarding RWI Coverage for Crucial IP Asset

Castle Harbour secured full RWI coverage for the acquisition of a pre-revenue AI company by resolving underwriter concerns over potential university IP claims tied to the company’s core technology.

…

Castle Harbour advised a financial sponsor in securing full RWI coverage for the acquisition of a pre-revenue AI company, despite a major red flag in diligence. The underwriter initially proposed excluding coverage for the company’s core AI technology, citing concerns that it may be subject to university IP claims under a research agreement– given that the founders had developed it at a time they were serving as professors at the university.

Drawing on its experience dealing with similar academic IP frameworks and a strong relationships with the underwriter, Castle Harbour was able to analyze the operative provision in the research agreement and advise the buyer and its IP counsel on what additional diligence could be done in order to confirm that no university resources were in fact used by the founders in developing the IP. As a result of these efforts, the exclusion was removed, and the buyer retained full coverage on the company’s most valuable asset.

Policy type: Buyer-side RWI
Size: $500MM - $1B
Sector: Technology

Buyer type: Financial Sponsor
Buyer jurisdiction: U.S.
Seller jurisdiction: U.S.

From Red Flag to Resolution: Insuring a Critical Tax Risk

Castle Harbour helped preserve deal momentum by identifying and insuring a material tax risk that threatened the target’s S-corporation status, avoiding retroactive tax liabilities.

…

Castle Harbour was engaged on a transaction where a material tax issue threatened to derail the deal: the target company’s tax efficient S-corporation status was at risk of being retroactively invalidated, potentially triggering significant unforeseen tax liabilities. Castle Harbour quickly identified the exposure during diligence and mobilized its internal tax specialists to assess the severity and structure a clear narrative for underwriters.

Through a coordinated effort with counsel, advisors, and Tax Insurance markets, tax insurance was successfully placed on the identified tax risk. By converting a potential deal-breaker into an insurable exposure, Castle Harbour preserved full deal momentum and provided the buyer with critical protection and peace of mind.

Policy type: Buyer-side RWI
Size: $500MM - $1B
Sector: Logistics

Buyer type: Financial Sponsor
Buyer jurisdiction: U.S.
Seller jurisdiction: U.S.