Engineering the purchase and sale of assets in a GP‑led secondary transaction requires a keen awareness of tax structuring issues that often bear little relationship to the issues typically negotiated in more traditional secondaries transactions. The complexity of those transactions continues to grow as they involve assets, investors and tax regimes spread throughout multiple jurisdictions. With that said, GPs of continuation funds enjoy significant flexibility to tailor bespoke structures and arrangements to optimize the tax treatment for all parties involved, particularly compared to traditional secondaries transactions. GPs leading continuation fund transactions can achieve optimal results for interested parties by using a range of vehicles and structures, as well as by thoughtfully addressing the issue in the transaction documents. This article examines the idiosyncrasies of tax structuring in the context of continuation funds, including the negotiating dynamics of GPs, rollover investors and new investors; key terms and issues to address in transaction documents; the additional tax flexibility they afford investors; and the complications introduced by related M&A transactions. See “Continuation Vehicles Survey Highlights Increasing Convergence of Some Terms, Vicissitudes Among Others” (May 29, 2025).