The received wisdom is that it is very difficult to mount a successful claim to claw back a redemption payment made to an investor in a Cayman fund. That view, which dates back to at least 2014 and the decision in Fairfield Sentry v. Migani (Fairfield Sentry), must now be revisited in light of a recent decision from the Cayman Islands courts. In a guest article, Peter McMaster QC and Mehreen Siddiqui, partner and associate, respectively, at Appleby, explain the most recent decision and examine why it undermines Fairfield Sentry, before discussing the possibilities that it opens up and its practical implications for fund managers. See “In Madoff-Related Litigation, Cayman Court of Appeal Holds That a Liquidator May Not Adjust a Shareholder’s NAV, Even When Based on Fictitious Profits” (May 17, 2018). For additional commentary from Appleby attorneys, see “How Fund Managers Should Prepare for the Cayman Islands Data Protection Law” (Sep. 12, 2019); and “Cayman Economic Substance Has Arrived: Steps In-Scope Fund Managers Must Take to Respond” (Jun. 27, 2019).