Chegg's Free Cash Flow Turns Negative - Just a Temporary Setback?

Key Takeaways Chegg's Q3 free cash flow turned negative largely due to one-time settlement and restructuring costs.Legacy subscription revenues are sliding as AI tools and search changes weigh on demand.Chegg's skilling pivot and discounted valuation may restore cash flow if execution stays on track.Chegg, Inc. (CHGG) reported negative free cash flow in the third quarter of 2025, which raised concerns about its financial trajectory. However, a closer look suggests the shortfall may be more transitional than ...