Datadog (DDOG) Stock Looks Undervalued Even After A 216% Run

Oct 23, 2026
datadog-(ddog)-stock-looks-undervalued-even-after-a-216%-run

Bailey Pemberton

4 min read

Datadog has delivered a powerful run over the past few years, helped by growing interest in observability tools and rising attention on AI workloads. With the share price now well above where it traded three years ago, the key question for investors is whether that move aligns with the cash the business can produce over time.

  • Datadog has returned 215.6% over the past three years, which places significant emphasis on the assumption that future cash flows can support this type of re-rating.

  • Recent analyst upgrades citing AI related demand and higher customer spending reflect expectations for stronger revenue and potentially larger future cash generation that may support the current valuation framework.

  • If you’d rather focus on sales, this one’s for you. See why Datadog’s 23.3x P/S tells a different valuation story.

The issue now is whether Datadog’s current share price is justified by the intrinsic value suggested by its cash flows.

If you want a broader starting point alongside Datadog, run a quick pass through 55 AI infrastructure stocks to see other stocks tied to the AI infrastructure build out.

Does Datadog Look Undervalued on Cash Flow?

The Discounted Cash Flow (DCF) model here focuses on the cash Datadog can return to shareholders over time. On the latest twelve month numbers, the business produced roughly $1.1b of free cash flow, and the projection set used in this DCF has that figure growing to over $4.2b by 2030. Those forecasts assume Datadog keeps expanding free cash flow rather than simply holding it flat, which puts a lot of weight on the durability of its product demand and pricing power.

Because the DCF projections put Datadog’s estimated intrinsic value meaningfully above the current share price of $257.75, the stock screens as undervalued on this cash flow lens. The recent Bernstein upgrade tied to AI related usage helps explain why expectations for future free cash generation are so strong, even if the market price has already moved sharply this year. For investors, the key question is whether that higher cash flow path proves realistic enough to close the gap implied by the model. Find out what Datadog could be worth using our Discounted Cash Flow (DCF) estimate.

The Datadog Narrative: What Would Justify Today’s Price?

Simply Wall St Narratives for Datadog pick up where that valuation puzzle leaves off by explaining which paths for Datadog’s growth, margins and earnings would need to occur for the stock to be worth meaningfully more or less than it is today. Each narrative links its figures to a specific view on how growth, profitability and risk might evolve, which you can revisit as fresh information on the business appears on the Community page.

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