A private fund is like a carefully built house of cards, with each piece methodically placed to optimize tax treatment for each type of investor. A secondary transaction can threaten the integrity of that structure unless thorough diligence is conducted pre-transaction to account for and address those issues. In addition, there are certain filings and representations tax filers need to make to the government to qualify for certain exemptions, all of which are best secured at the outset of the secondary transaction. Those and other key U.S. tax issues for secondary transactions were addressed in a Strafford CLE webinar featuring Mayer Brown partners Matthew A. McDonald and JoonBeom Pae. This second article in a two-part series describes various tax considerations for the outset of a secondary transaction, including tax elections; allocation of taxes and expenses; and withholding tax certificates. The first article detailed the importance of conducting diligence on fund agreements to ensure compliance with transfer restrictions meant to avoid negative tax ramifications. For more on the secondary market in the current climate, see “Considerations When Using Earn‑Outs to Consummate Secondary Transactions During a Downturn” (Jun. 16, 2020); and “Evolution and Future of GP‑Led Restructurings: Transaction Structuring Trends and Conflicts of Interest Management (Part One of Two)” (Jun. 2, 2020).