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Currently, SFTs have their own contractual provisions in the event of a settlement fail, laid out in the relevant GMRAs and GMSLAs. Buy-ins, as utilized in the outright cash markets, generally do not apply to SFTs. However, under the new regulation, SFTs with terms of 30 business-days or longer will be in scope of the mandatory buy-in provisions. This creates a number of complications and ambiguities which the paper seeks to explore and discuss. In doing so, it also intends to lay the ground-work for constructive dialogue between market participants and the regulatory authorities to resolve the various challenges and support successful implementation, with minimal disruption to market functioning and liquidity.