Guidewire Software stock edges lower as insiders plan tax-cover share sales

Published on 09/18/2026 at 14:29 | Editorial responsibility: Rafael Müller, Editor-in-Chief AD HOC NEWS

Guidewire Software stock closed at USD 145.11 on September 17, 2026 on the NYSE, about 43% below the consensus target of USD 216.23. Recent Rule 144 filings show planned insider share sales tied to RSU and PSU vesting on September 15, 2026, mainly to cover tax obligations.

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Guidewire Software, Inc. stock (ISIN US4016171054) closed at USD 145.11 on the New York Stock Exchange on September 17, 2026, down 1.10% from the prior close, leaving the shares well below a consensus analyst price target of USD 216.23.

Insider tax-cover sales set around September 15, 2026 vesting

According to a Form 144 notice reported by StockTitan on September 17, 2026, Guidewire’s chief financial officer Jeffrey Elliott Cooper may sell up to 23,234 shares of Guidewire common stock under Rule 144, with an aggregate market value of USD 3,356,657.73 based on prevailing prices and share data in the notice.

The same filing notes that 81,992,669 Guidewire Software common shares were outstanding as of September 17, 2026, and explains that the planned transactions are automatic sell-to-cover operations to satisfy tax withholding obligations under Guidewire’s Amended and Restated 2020 Stock Plan, tied to restricted stock units and performance stock units vesting on September 15, 2026.StockTitan

Additional Rule 144 notice from general counsel

A separate Rule 144 filing summarized by StockTitan on September 17, 2026 states that Guidewire’s chief administrative officer and general counsel James Winston King has also notified of planned sales of Guidewire common stock under Rule 144 in connection with equity awards vesting on September 15, 2026.

The notice lists RSU-related Guidewire common stock amounts of 861 shares from a grant dated September 15, 2022, 905 shares from a grant dated September 13, 2023, 560 shares from a grant dated September 11, 2024, and 355 shares from a grant dated September 11, 2025, all vesting on September 15, 2026.StockTitan In addition, the filing highlights a performance stock unit vest of 19,701 shares granted on September 13, 2023, also scheduled to vest on September 15, 2026 and reported as acquired as compensation.StockTitan

Stock valuation, price targets and market metrics

Per data compiled by MarketBeat as of the close on September 17, 2026, Guidewire Software shares finished that trading day at USD 145.11, down USD 1.62 or 1.10%, within a daily range between USD 142.23 and USD 146.00.

Over the prior year, the stock traded in a 52-week range from USD 102.30 to USD 255.89, so the September 17, 2026 closing price sits about 41.6% below the 52-week high and roughly 41.9% above the 52-week low based on those figures.MarketBeat MarketBeat cites a market capitalization of USD 12.08 billion for Guidewire at that price level, and an indicated trailing twelve-month earnings per share of USD 1.63, implying a price-to-earnings ratio of 89.03.MarketBeat

Analyst data aggregated by MarketBeat show that Guidewire Software has a consensus rating of Moderate Buy from 16 analysts, with no strong buy or sell ratings, 12 buy ratings and 4 hold ratings.MarketBeat The consensus price target stands at USD 216.23, with a high target of USD 258.00 and a low of USD 181.00, implying roughly 49.0% upside from the September 17, 2026 closing price of USD 145.11 if the average target is reached.MarketBeat

Earnings context and cloud transition narrative

MarketBeat’s overview also references recent commentary that Guidewire Software stock fell on cautious guidance tied to its cloud transition, even though revenue and margins improved.MarketBeat While the exact quarterly reporting period is not fully detailed in that snippet, the discussion points to a trade-off between near-term growth and longer-term cloud economics, which investors often weigh when assessing valuation.

A separate snippet on Yahoo Finance highlights that Guidewire grew fiscal 2026 annual recurring revenue by 19%, underscoring that subscription and cloud-based revenue streams are a key driver of the company’s business model in its latest reported fiscal year.Yahoo Finance For investors, the combination of improving recurring revenue and cautious guidance can translate into a more balanced risk-reward profile, where execution on cloud migration remains central.

Ownership structure and upcoming earnings date

Major-holder data compiled by Yahoo Finance show that institutional investors and funds hold a significant portion of Guidewire’s outstanding shares, although the detailed table of holders and percentages is not fully visible in the search snippet.

In addition, an earnings events overview that includes Guidewire’s ticker indicates a scheduled earnings event on September 24, 2026, suggesting that the company is expected to report new quarterly figures on that date.Yahoo Finance That upcoming report will give the market fresh data on revenue growth, margins and guidance, which could either reinforce or challenge the current analyst targets and valuation multiples.

Guidewire Software stock level and investor perspective

As of the last completed trading day on September 17, 2026, Guidewire Software stock closed at USD 145.11 on the New York Stock Exchange, with a market capitalization of USD 12.08 billion at that price level and a 52-week trading span between USD 102.30 and USD 255.89. The shares therefore trade at a marked discount to the consensus analyst price target of USD 216.23, while insider Rule 144 filings show tax-driven sell-to-cover transactions around RSU and PSU vesting on September 15, 2026 rather than discretionary open-market sales.