As of FY2024, Cloudflare serves 35% of Fortune 500 companies, reaches ~95% of internet users within ~50ms globally, and operates at a 77% GAAP gross margin with a 42%+ revenue CAGR (FY2019–FY2024). These strong fundamentals set the stage for our discounted cash flow (DCF) analysis, examining whether Cloudflare can feasibly grow to $5 billion in Annual Recurring Revenue (ARR) by 2028. We forecast Cloudflare’s financials over 2025–2028 and discount the cash flows to present value, testing key assumptions on growth and risk. Below we detail the forecast, free cash flow projections, valuation, and sensitivity analysis on critical variables like revenue growth and discount rate, before concluding on the target’s feasibility.