We document substantial long-run post-issue underperformance by firms making straight and convertible debt offerings from 1975 to 1989. This long-run underperformance is more severe for smaller, younger, and NASDAQ-listed firms, and for firms issuing speculative grade debt. We also find strong evidence that the underperformance of issuers of both straight and convertible debt is limited to those issues that occur in periods with a high volume of issues. In contrast to earlier event studies that found insignificantly negative abnormal returns at the time of debt issue announcements and concluded that debt offerings had no impact on shareholder wealth, our results suggest that debt offerings, like equity offerings, are signals that the firm is overvalued. As with equity offerings and repurchases, the market appears to underreact at the time of the debt offering announcement so that the full impact of the offering is only realized over a longer time horizon. (C) 1999 Elsevier Science S.A. All rights reserved.