BENTLEY GREGORY S

SEC source: 0001104659-23-126960 · tm2333034-7_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,510,717

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-113396 · tm2327552-6_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,508,422

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 31, 2023 at prices ranging from $48.085 to $48.62. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-113396 · tm2327552-6_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,526,387

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 30, 2023 at prices ranging from $48.03 to $48.74. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-112576 · tm2327552-4_4seq.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,593,700

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 27, 2023 at prices ranging from $48.01 to $48.96. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-112576 · tm2327552-4_4seq.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,644,605

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 26, 2023 at prices ranging from $49.31 to $49.57. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-112576 · tm2327552-4_4seq.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,646,804

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 26, 2023 at prices ranging from $48.29 to $49.27. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-111748 · tm2327552-2_4seq1.xml · nonDerivative · entry 4

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,756,334

F6 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Company's Bonus Pool Plan.

SEC source: 0001104659-23-111748 · tm2327552-2_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,681,311

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 25, 2023 at prices ranging from $49.805 to $50.36. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-111748 · tm2327552-2_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,698,107

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 25, 2023 at prices ranging from $48.80 to $49.745. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-111748 · tm2327552-2_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,738,312

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 24, 2023 at prices ranging from $49.745 to $50.47. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-100461 · tm2325380-3_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,817,649

SEC source: 0001104659-23-096023 · tm2322724-7_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,837,910

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-086391 · tm2321095-7_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,835,360

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 31, 2023 at prices ranging from $53.11 to $53.74. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-086391 · tm2321095-7_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,876,746

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 28, 2023 at prices ranging from $53.01 to $53.7125. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 5

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,922,617

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F7 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 27, 2023 at prices ranging from $53.40 to $53.625. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 4

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,939,535

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 27, 2023 at prices ranging from $52.39 to $53.36. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,965,230

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 26, 2023 at prices ranging from $52.62 to $53.52. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,006,831

F2 · kind: Represents shares withheld by the Issuer to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,032,940

F1 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Issuer's Bonus Pool Plan (the "Bonus Pool Payment").

SEC source: 0001104659-23-084299 · tm2321095-4_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,973,588

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 25, 2023 at prices ranging from $53.89 to $54.00. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-084299 · tm2321095-4_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,978,727

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 25, 2023 at prices ranging from $52.89 to $53.88. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-084299 · tm2321095-4_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,070,445

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 24, 2023 at prices ranging from $52.81 to $53.66. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-073763 · tm2317958-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,128,141

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-059769 · tm2314780-3_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,125,905

SEC source: 0001104659-23-059769 · tm2314780-3_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,136,962

F1 · kind: Represents a private sale of Class B Common Stock to a family trust in satisfaction of a prior obligation.

SEC source: 0001104659-23-054385 · tm2314141-1_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,266,653

F2 · kind: Represents shares withheld by the Issuer to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

SEC source: 0001104659-23-054385 · tm2314141-1_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,310,325

F1 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Issuer's Bonus Pool Plan (the "Bonus Pool Payment").

SEC source: 0001104659-23-050367 · tm2313339-5_4seq1.xml · nonDerivative · entry 4

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,211,049

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

SEC source: 0001104659-23-050367 · tm2313339-5_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,211,289

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 25, 2023 at prices ranging from $40.98 to $41.94. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-050367 · tm2313339-5_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,228,960

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

SEC source: 0001104659-23-050367 · tm2313339-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,229,060

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 24, 2023 at prices ranging from $41.85 to $42.77. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-033924 · tm238296-19_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,274,683

SEC source: 0001104659-23-030615 · tm238296-7_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,287,277

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-007041 · tm231633-11_4seq1.xml · nonDerivative · entry 4

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,284,318

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on January 25, 2023 at prices ranging from $36.59 to $37.39. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-007041 · tm231633-11_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,297,842

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on January 24, 2023 at prices ranging from $38.21 to $38.665. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-23-007041 · tm231633-11_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,347,952

F2 · kind: Represents shares withheld by the Company to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

SEC source: 0001104659-23-007041 · tm231633-11_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,387,006

F1 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Company's (as defined below) Bonus Pool Plan (the "Bonus Pool Payment").

SEC source: 0001104659-23-001483 · tm231633-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,298,785

F1 · kind: Represents shares of Class B Common Stock withheld by the Issuer to cover taxes due by the Reporting Person upon a scheduled distribution of Class B Common Stock from the Issuer's Non-Qualified Deferred Compensation Plan.

SEC source: 0001104659-22-126304 · tm2232398-2_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,566,363

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-22-126304 · tm2232398-2_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,564,064

SEC source: 0001104659-22-118516 · tm2230154-2_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,566,154

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on November 10, 2022 at prices ranging from $36.975 to $37.165. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-117165 · tm2230154-1_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,592,671

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on November 8, 2022 at prices ranging from $36.00 to $36.32. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-112502 · tm2229121-1_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,680,202

F1 · kind: As previously disclosed by Bentley Systems, Incorporated ( the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on October 27, 2022 at prices ranging from $36.00 to $36.11. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-112502 · tm2229121-1_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,733,150

F3 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Company's Bonus Pool Plan.

SEC source: 0001104659-22-112502 · tm2229121-1_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,634,484

F1 · kind: As previously disclosed by Bentley Systems, Incorporated ( the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

SEC source: 0001104659-22-100834 · tm2225081-7_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,636,152

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-22-100108 · tm2225081-3_4seq1.xml · nonDerivative · entry 4

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,633,585

SEC source: 0001104659-22-100108 · tm2225081-3_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,640,085

F1 · kind: As previously disclosed by Bentley Systems, Incorporated ( the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 13, 2022 at prices ranging from $35.665 to $36.64. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-100108 · tm2225081-3_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,731,799

F1 · kind: As previously disclosed by Bentley Systems, Incorporated ( the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 12, 2022 at prices ranging from $38.42 to $38.54. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-100108 · tm2225081-3_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,734,701

F1 · kind: As previously disclosed by Bentley Systems, Incorporated ( the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 12, 2022 at prices ranging from $37.42 to $38.41. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.