O'Toole Brian E

SEC source: 0001753539-26-000147 · wk-form4_1790113118.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 1,043,396

F1 · kind: This transaction was executed pursuant to a Rule 10b5-1 trading plan adopted by the reporting person in June 2026.

F2 · price: This transaction was executed in multiple trades at prices ranging from $22.28 to $23.12. The price reported above reflects the weighted average sale price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-26-000145 · wk-form4_1789418192.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,063,396

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person. The "Amount" and "Price" reported in this Column 4 reflect the aggregate number and weighted-average price, respectively, of shares sold.

F2 · price: This transaction was executed in multiple trades at prices ranging from $20.60 to $21.34. The price reported above reflects the weighted average sale price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-26-000137 · wk-form4_1789072189.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 1,119,676

F1 · kind: This transaction was executed pursuant to a Rule 10b5-1 trading plan adopted by the reporting person in June 2026.

F2 · price: This transaction was executed in multiple trades at prices ranging from $21.52 to $22.23. The price reported above reflects the weighted average sale price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-26-000084 · wk-form4_1781294677.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,139,676

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person. The "Amount" and "Price" reported in this Column 4 reflect the aggregate number and weighted-average price, respectively, of shares sold.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

F3 · balance_after: The Form 4 filed on September 15, 2025 (the "Original Form 4") and the Form 4/A filed on October 17, 2025 (the "Original Form 4/A") erroneously reflected an incorrect vesting schedule. One third (1/3rd) of the RSUs are scheduled to vest on September 10, 2026, and thereafter, one twelfth (1/12th) of the total number of RSUs are scheduled to vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December 10), subject to the named executive officer continuing to be a service provider through the applicable vesting date. The Amount of Securities Beneficially Owned Following Reported Transactions represented on the Original Form 4 and the Original Form 4/A was correctly reported.

SEC source: 0001753539-26-000025 · wk-form4_1773347324.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 963,522

F1 · kind: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-26-000025 · wk-form4_1773347324.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,155,188

F3 · kind: These securities are restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of Class A Common Stock. The RSUs will vest as follows: one-fourth of the RSUs will vest on March 10, 2027, and thereafter, one-sixteenth of the total number of RSUs will vest quarterly on the 10th day of the third month of each quarter (March 10 June 10, September 10 and December 10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-25-000138 · wk-form4_1765573535.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 988,521

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person. The "Amount" and "Price" reported in this Column 4 reflect the aggregate number and weighted-average price, respectively, of shares sold.

SEC source: 0001443092-25-000012 · wk-form4_1757968422.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,000,164

F2 · shares: These securities are restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of Class A Common Stock. The RSUs will vest as follows: one-third will vest on September 10, 2026, and thereafter one-twelfth of the total number of RSUs will vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December 10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

SEC source: 0001443092-25-000015 · wk-form4a_1760731533.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,001,937

F3 · shares: These securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock. The restricted stock units are granted pursuant to the BlackSky Technology Inc. 2021 Equity Incentive Plan. The number of restricted stock units was calculated based on the closing price of a share of BlackSky Technology Inc.'s Class A Common Stock on the New York Stock Exchange on September 9, 2022. The restricted stock units will vest as follows: one-fourth (1/4th) of the RSUs will vest on September 10, 2023, and thereafter, one sixteenth (1/16th) of the total number of RSUs will be scheduled to vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December 10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

F2 · balance_after: The original Form 4, filed September 15, 2025, incorrectly reported details of the transaction, which have been corrected.

SEC source: 0001443092-25-000015 · wk-form4a_1760731533.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 751,937

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person. The "Amount" and "Price" reported in this Column 4 reflect the aggregate number and weighted-average price, respectively, of shares sold.

F2 · balance_after: The original Form 4, filed September 15, 2025, incorrectly reported details of the transaction, which have been corrected.

SEC source: 0001443092-25-000012 · wk-form4_1757968422.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 750,164

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person. The "Amount" and "Price" reported in this Column 4 reflect the aggregate number and weighted-average price, respectively, of shares sold.

SEC source: 0001443092-25-000004 · wk-form4_1749760031.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 783,456

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-25-000012 · wk-form4_1741813607.xml · derivative · entry 3

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 210,834

Underlying: Class A Common Stock · 210,834 shares

Expires 2035-03-10

F4 · derivative.exercise_date: Each Option represents a right to purchase the underlying securities of the Issuer reported in Table II. The options are granted pursuant to the BlackSky Technology Inc. 2021 Equity Incentive Plan. The number of options and exercise price for the options was calculated based on the closing price of a share of BlackSky Technology Inc.'s Class A Common Stock on the New York Stock Exchange on March 10, 2025. The shares subject to the Option will vest as follows: one fourth (1/4th) of the award will vest on the March 10, 2026 and thereafter, one forty-eighth (1/48th) of the award will be scheduled to vest monthly on the 10th day of each month, subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

SEC source: 0001753539-25-000012 · wk-form4_1741813607.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 790,391

F3 · kind: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-25-000012 · wk-form4_1741813607.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 797,326

F1 · kind: These securities are restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of Class A Common Stock. The RSUs will vest as follows: one-fourth of the RSUs will vest on March 10, 2026, and thereafter, one-sixteenth of the total number of RSUs will vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-24-000152 · wk-form4_1734042918.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 691,909

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person.

SEC source: 0001753539-24-000122 · wk-form4_1727467786.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 698,929

F3 · shares: These securities are restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of Class A Common Stock. The RSUs will vest as follows: one-fourth of the RSUs will vest on September 10, 2025, and thereafter, one-sixteenth of the total number of RSUs will vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

F4 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-24-000122 · wk-form4_1727467786.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 479,785

F1 · shares: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person.

F2 · balance_after: The reported number of shares has been adjusted to reflect the impact of the issuer's 1-for-8 reverse stock split completed on September 6, 2024.

SEC source: 0001753539-24-000068 · wk-form4_1718136463.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,033,107

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

SEC source: 0001753539-24-000021 · wk-form4_1710191023.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,045,392

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

SEC source: 0001443092-23-000007 · wk-form4_1702416747.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,127,085

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

SEC source: 0001443092-23-000003 · wf-form4_169465609007359.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,208,779

F3 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested RSUs and not a market transaction.

SEC source: 0001443092-23-000003 · wf-form4_169465609007359.xml · derivative · entry 3

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 900,000

Underlying: Class A Common Stock · 900,000 shares

Expires 2033-09-10

F4 · derivative.exercise_date: The shares subject to the option will vest as follows: one-third of the award will vest on September 10, 2024 and thereafter, one thirty-sixth of the award will vest monthly on the 10th day of each month, subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

SEC source: 0001443092-23-000003 · wf-form4_169465609007359.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,327,325

F1 · shares: These securities are restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of Class A Common Stock. The RSUs will vest as follows: one-fourth of the RSUs will vest on September 10, 2024, and thereafter, one-sixteenth of the total number of RSUs will vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December 10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-23-000049 · wf-form4_168677883478543.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,795,042

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-23-000017 · wf-form4_167901268914928.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,864,450

F1 · kind: Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units (RSUs) and does not represent a discretionary sale by the Reporting Person.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-22-000104 · wf-form4_167089372587461.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,940,110

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001443092-22-000004 · wf-form4_166311213722345.xml · nonDerivative · entry 2

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,009,518

F3 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the net settlement of vested restricted stock units (RSUs) and not a market transaction.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001443092-22-000004 · wf-form4_166311213722345.xml · derivative · entry 3

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 871,626

Underlying: Class A Common Stock · 871,626 shares

Expires 2032-09-10

F4 · derivative.exercise_date: Each Option represents a right to purchase the underlying securities of the Issuer reported in Table II. The options are granted pursuant to the BlackSky Technology Inc. 2021 Equity Incentive Plan. The number of options and exercise price for the options was calculated based on the closing price of a share of BlackSky Technology Inc.'s Class A Common Stock on the New York Stock Exchange on September 9, 2022. The shares subject to the Option will vest as follows: one fourth (1/4th) of the award will vest on the September 10, 2023 and thereafter, one forty-eighth (1/48th) of the award will be scheduled to vest monthly on the 10th day of each month, subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

SEC source: 0001443092-22-000004 · wf-form4_166311213722345.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,078,926

F1 · security: These securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock. The restricted stock units are granted pursuant to the BlackSky Technology Inc. 2021 Equity Incentive Plan. The number of restricted stock units was calculated based on the closing price of a share of BlackSky Technology Inc.'s Class A Common Stock on the New York Stock Exchange on September 9, 2022. The restricted stock units will vest as follows: one-fourth (1/4th) of the RSUs will vest on September 10, 2023, and thereafter, one sixteenth (1/16th) of the total number of RSUs will be scheduled to vest quarterly on the 10th day of the third month of each quarter (March 10, June 10, September 10, December 10), in each case subject to the Reporting Person continuing to be a service provider through the applicable vesting date.

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001443092-22-000002 · wf-form4_165529297907762.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,643,113

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the vesting of restricted stock units (RSUs).

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

SEC source: 0001753539-22-000013 · wf-form4_164737557890892.xml · nonDerivative · entry 1

O'Toole Brian E · CIK 0001443092 · Director · CEO and President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,712,521

F1 · shares: Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the vesting of restricted stock units (RSUs).

F2 · balance_after: Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Class A Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

F3 · balance_after: Represents adjustment of incorrect RSU awards and common stock reported on a Form 3 filed on September 16, 2021. The correct numbers were 2,462,359 RSUs and 805,424 common stock.