This study examines whether and how accounting conservatism influences managerial discretion over semantic progression in the Management’s Discussion and Analysis (MD&A) portion of 10-K filings. I utilize natural language processing techniques to capture circuitousness, a semantic progression measure that reflects whether the text in a document is “going in circles.” I find a significant negative association between conservatism and circuitousness. In the cross-sectional analysis, I find that the negative relationship is pronounced among firms with higher long-term debt and those operating in more competitive product markets. Additionally, I find that the timeliness of news recognition is less asymmetric among firms with more circuitous reports. Collectively, the results highlight the governance role of accounting conservatism, promoting transparent and reliable financial reporting.