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Bentley Systems insider sale: Gregory S. Bentley, Executive Chair & President and a director who is also a >10% owner, reported a sale of 37,160 Class B common shares on 09/02/2025 at a reported price of $54.8325 per share. After the transaction the filing shows 7,580,436 shares beneficially owned directly. The report also discloses 29,155 shares indirectly held by his spouse and 92,654 shares indirectly held through a 401(k) plan. The filing states the sale was a private sale to a family trust to satisfy a prior obligation. The Form 4 was signed by an attorney-in-fact on 09/04/2025.

Bentley Systems insider transaction: Chief Legal Officer David R. Shaman reported a sale of 6,685 shares of Class B common stock on 08/31/2025 at a volume-weighted average price of $55.03 per share. After the reported disposition, the Form 4 lists 639,323 shares beneficially owned directly and additional indirect holdings of 279,308 shares by Grantor Retained Annuity Trusts, 55,527 by a spouse trustee and 32,635 through a 401(k) plan. The filing notes the 6,685 shares were withheld by the issuer to cover taxes related to a scheduled distribution from the issuer's Non-Qualified Deferred Compensation Plan. The form is signed by an attorney-in-fact on 09/03/2025.

Gregory S. Bentley, Executive Chair & President of Bentley Systems (BSY), reported an insider transaction dated 08/27/2025. The filing shows a disposition of 351 Class B common shares (transaction code G) with a reported price of $0.00, and total beneficial ownership following the transaction of 7,617,596 shares held directly. The report also discloses 29,155 shares held indirectly by spouse and 92,654 shares held indirectly via a 401(k) plan.

Bentley Systems insider Keith A. Bentley reported changes in beneficial ownership on Form 4 dated 08/22/2025. The filing discloses a transfer of 100,000 shares of Class B common stock from the reporting person’s spouse to joint ownership with the reporting person, recorded as a disposition and an acquisition under the applicable transaction codes. After the reported transactions the reporting person is shown owning 3,959,327 shares directly. The filing also reports 12,696,921 shares indirectly held by a Grantor Retained Annuity Trust and 92,654 shares indirectly through a 401(k) plan. The Form 4 was signed by an attorney-in-fact on 08/26/2025.

Bentley Systems director and Executive Chair & President Gregory S. Bentley reported a sale of 9,349 Class B common shares on 08/21/2025, at a reported price of $0.00 (transaction code G). After the sale, Mr. Bentley directly beneficially owns 7,617,947 Class B shares. The filing also discloses 29,155 shares held indirectly by his spouse and 92,654 shares held indirectly via a 401(k) plan.

Bentley Systems (BSY) submitted a Form 144 proposing the sale of 300 shares of Class B common stock through Charles Schwab, with an aggregate market value of $16,069.50, scheduled approximately for 08/18/2025. The 300 shares were acquired as a gift from Keith Bentley on 10/15/2015. The filing lists multiple related sales during the past three months, including a sale of 150,000 shares on 07/07/2025 for $8,326,003.40 and sizable distributions on 08/13/2025 and 08/14/2025 producing proceeds in the hundreds of thousands to millions of dollars for various gift trusts. The filer represents no undisclosed material adverse information and certifies compliance with applicable trading rules.

Bentley Systems (BSY) Form 144: The filer notifies a proposed sale of 25,000 Class B common shares through Charles Schwab with an aggregate market value of $1,347,000, scheduled approximately for 08/18/2025. The filing shows there are 292,093,306 Class B shares outstanding. The shares to be sold were acquired as a gift from Keith Bentley on 10/15/2015. The filing also discloses multiple recent insider-related sales during May–August 2025, including a 150,000-share sale on 07/07/2025 that generated $8,326,003.40 and several 08/13�08/14/2025 transfers from related gift trusts. The notice includes the standard Rule 144 representation regarding absence of undisclosed material adverse information.

Joseph P. Logan reports beneficial ownership of 13,335,473 shares of Class B common stock of Bentley Systems held through four separate gift trusts of which he is trustee. The shares were previously owned by the Gregory S. Bentley 2009 Gift Trust, which was divided into the four trusts after Mr. Logan was appointed trustee of the Original Trust on June 2, 2023. Mr. Logan holds sole voting and sole dispositive power over the reported shares, which represent 4.6% of the Class B shares outstanding based on 292,093,306 shares disclosed by the issuer. The filing includes a certification that the securities were not acquired to change or influence control of the issuer.

Bentley Systems filed a Form 144 disclosing a proposed sale of 55,000 shares of Class B common stock through Charles Schwab, with an aggregate market value of $2,885,850 and an approximate sale date of 08/12/2025 on Nasdaq.

The filing shows the 55,000 shares were acquired as a gift from Keith Bentley on 02/23/2017 (the donor originally acquired the securities on 08/14/1987). The notice also lists related sales in May–July 2025, including a 149,991-share sale on 07/07/2025 for $8,326,003.40 and several smaller dispositions in late May 2025. The signer certifies there is no undisclosed material adverse information.