When a federally chartered development bank reviews its exposure to a defaulting technology software company in Kelowna, British Columbia, the natural instinct is to calculate what remains owing and pursue the borrower and its sole shareholder guarantor for the outstanding balance. Yet a sophisticated lender facing a January 2025 default on $318,174 in accumulated obligations will quickly turn its attention to a second question: during the months leading up to that default, did the borrower transfer value to other creditors in ways that diminished the pool of assets otherwise available to satisfy the development bank's claims? This question sits at the heart of preference law, a body of rules that allows certain creditors or a trustee in bankruptcy to claw back payments made during a defined period before insolvency, restoring those sums to the collective estate for distribution according to statutory priority. For the development bank that extended 9 loans totaling $570,000 between 2018 and 2024, preference analysis is not merely academic; it represents a potential avenue to augment recovery in circumstances where the borrower's revenue collapsed from $1.09 million in 2018 to $225,000 by 2023, where cumulative deficits reached $469,000, and where monthly obligations escalated from $2,500 to $12,000 without corresponding capacity to service the debt. Understanding when and how preference challenges succeed — and when they fail — is essential for any professional monitoring loan-cycling risk in serial lending arrangements.