This study empirically investigates the long-term impact of listing regulation relaxation on corporate risk, focusing on South Korea's unique "Technology-Based Special Listing" system. In line with the global trend of lowering entry barriers for innovative startups, such as the U.S. JOBS Act, South Korea introduced this scheme to enable technologically advanced firms to be listed on the KOSDAQ market. This system is particularly vital for R&D-intensive sectors such as biotechnology, artificial intelligence, and semiconductors, providing them with access to essential funding even before meeting traditional financial milestones, including profitability or specific revenue targets. While this policy fosters innovation, it also introduces significant investment risks driven by financial instability and heightened information asymmetry. Using stock return volatility as the primary proxy for investment risk, this research compares technology special listing firms with general IPO firms listed on the KOSDAQ market from 2014 to 2022. The research dataset was constructed by integrating listing data from the Korea Exchange's (KRX) KIND system with financial and stock price information from the TS2000 database provided by the Korea Listed Companies Association. The final sample consists of 527 firms, including 149 technology special listing firms. To analyze firm-level risk, the study employs a multi-regression framework, controlling for firm characteristics such as firm size, leverage, return on assets (ROA), cash flow, and market-to-book ratios. The empirical results reveal that technology special listing firms exhibit significantly higher stock return volatility during their first year of listing compared to general IPO firms. This elevated initial risk is primarily attributed to two structural factors: the absence of conventional financial requirements leading to lower financial stability, and substantial information asymmetry inherent in firms whose value is primarily driven by intangible assets like technological potential. For these firms, the lack of a proven financial track record and a reliance on future growth expectations make their stock prices more sensitive to external shocks and market sentiment. However, a key finding of this research is that this volatility gap narrows considerably over the subsequent two to three years. As firm-specific information regarding technological progress and business milestones is disseminated into the market in a timely manner, the initial uncertainty is mitigated, leading to a stabilization of stock prices. Interestingly, while information asymmetry—measured through proxies like trading volume—significantly reduced over time, the study did not find a statistically significant improvement in the fundamental financial soundness of these firms during the same period. This suggests that the long-term reduction in stock return volatility is driven more by the resolution of information uncertainty through market learning than by fundamental financial recovery. To ensure the robustness of the findings, the study implemented several advanced econometric tests. First, the baseline risk measure was supplemented by employing market-adjusted return volatility and idiosyncratic risk. Second, the analysis was restricted to specific industries, such as medical and R&D sectors, where special listings are most prevalent, to control for industry-specific effects. Finally, to mitigate potential selection bias and omitted variable concerns, the research utilized Propensity Score Matching (PSM) and industry-specific 1:1 matching to compare special listing firms with general IPO firms of similar characteristics. The results remained consistent across all robustness checks. The findings of this research offer several contributions to both academia and practice. First, it adds to the global literature on the effects of listing regulation relaxation by providing detailed empirical evidence from the Korean market, highlighting the dual nature of capital access and investor protection. Second, unlike previous studies that focused primarily on the short-term performance or qualitative characteristics of special listing firms, this study provides a comprehensive long-term analysis of investment risk dynamics. It highlights the role of timely and transparent disclosure in reducing market uncertainty over time. For policymakers and regulators, these results suggest that while relaxing financial entry barriers is an effective tool for promoting industrial innovation, such measures must be complemented by robust disclosure requirements and institutional monitoring to protect investors and maintain market trust. For investors, the research provides a balanced perspective, emphasizing that the high initial volatility of technical listing firms is a characteristic of their unique information environment rather than a permanent state of instability. Ultimately, the study confirms that as the market processes and incorporates firm-specific information, the risks associated with innovative but financially unproven firms tend to stabilize.