Fifth Street Finance, later known as OCSL (Oaktree Specialty Lending Corporation) faced significant scrutiny regarding its Dividend Reinvestment Plan (DRIP) and overall dividend policy, particularly in the years leading up to its acquisition by Oaktree. Understanding how the DRIP functioned and the criticisms leveled against it requires examining Fifth Street’s broader financial context. The DRIP allowed shareholders to reinvest their cash dividends back into Fifth Street stock, often at a price slightly below market value. The supposed benefit was two-fold: it provided existing shareholders with the opportunity to increase their holdings cost-effectively and allowed Fifth Street to raise capital without directly issuing new shares through the open market. This conserved cash and potentially avoided dilution for shareholders not participating in the DRIP. However, the core issue stemmed from the sustainability of Fifth Street’s high dividend yield in the face of declining net investment income (NII). The company, structured as a Business Development Company (BDC), was required to distribute a significant portion of its taxable income to shareholders to maintain its tax-advantaged status. As Fifth Street’s investments faced challenges and its NII faltered, maintaining those high dividends became increasingly problematic. Critics argued that the DRIP became a way for Fifth Street to essentially fund its dividends, in part, by selling new shares to existing investors *at a discount*. This created a potential conflict of interest. While the DRIP appeared attractive to shareholders on the surface, the underlying reality was that the company was potentially using new equity to pay for distributions rather than relying solely on income generated from its investments. The problem intensified when Fifth Street was forced to reduce its dividend multiple times. Each dividend cut eroded shareholder confidence and further highlighted the unsustainability of the previous, seemingly generous, payouts. The DRIP, rather than being a benefit, became a constant reminder of the company’s financial struggles and the declining value of its stock. Furthermore, concerns arose regarding the accounting practices and overall management of Fifth Street leading up to the Oaktree acquisition. Questions were raised about the valuation of its investment portfolio and the adequacy of its reserves for potential loan losses. These uncertainties, coupled with the reliance on the DRIP to supplement dividend payments, fueled negative sentiment among investors. Ultimately, the DRIP, intended as a shareholder-friendly initiative, contributed to the narrative of a company struggling to maintain its high dividend yield. While reinvesting dividends can be a sound strategy, it becomes questionable when the underlying profitability of the company is in doubt. The experience with Fifth Street’s DRIP serves as a cautionary tale about the importance of evaluating the long-term sustainability of a company’s dividend policy and the potential risks associated with relying on reinvestment plans to artificially inflate returns. The acquisition by Oaktree and the subsequent name change marked a significant turning point, hopefully signaling a more sustainable and transparent approach to dividend management.