ROOT · Root, Inc.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

Represents the grant of restricted stock units in accordance with the Issuer's Non-Employee Director Compensation Policy.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

The shares were sold pursuant to a 10b5-1 trading plan.

The shares were sold pursuant to a 10b5-1 trading plan.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

The shares were sold pursuant to a 10b5-1 trading plan.

The shares were sold pursuant to a 10b5-1 trading plan.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

Each Performance-Based Restricted Stock Unit ("PSU") represents a contingent right to receive one share of ROOT Class A common stock. The PSUs vest in tranches of 14,348 on April 1, 2024; 28,695 on April 1, 2025; 43,043 on April 1, 2026; and 57,390 on April 1, 2027 and upon ROOT Class A common stock achieving a specified price per share over 45 consecutive trading days after such dates. Per share price achievement levels for the four tranches are: $16.76; $25.14; $33.52; and $41.90.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

Each Performance-Based Restricted Stock Unit ("PSU") represents a contingent right to receive one share of ROOT Class A common stock. The PSUs vest in tranches of 1,592 on April 1, 2024; 3,184 on April 1, 2025; 4,777 on April 1, 2026; and 6,369 on April 1, 2026 and upon ROOT Class A common stock achieving a specified price per share over 45 consecutive trading days after such dates. Per share price achievement levels for the four tranches are: $16.76; $25.14; $33.52; and $41.90.

Each Performance-Based Restricted Stock Unit ("PSU") represents a contingent right to receive one share of ROOT Class A common stock. The PSUs vest in tranches of 2,147 on April 1, 2024; 4,295 on April 1, 2025; 6,442 on April 1, 2026; and 8,589 on April 1, 2027 and upon ROOT Class A common stock achieving a specified price per share over 45 consecutive trading days after such dates. Per share price achievement levels for the four tranches are: $16.76; $25.14; $33.52; and $41.90.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

Each Performance-Based Restricted Stock Unit ("PSU") represents a contingent right to receive one share of ROOT Class A common stock. The PSUs vest in tranches of 20,990 on April 1, 2024; 41,979 on April 1, 2025; 62,969 on April 1, 2026; and 83,958 on April 1, 2027 and upon ROOT Class A common stock achieving a specified price per share over 45 consecutive trading days after such dates. Per share price achievement levels for the four tranches are: $16.76; $25.14; $33.52; and $41.90.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

The shares were sold pursuant to a 10b5-1 trading plan.

The shares were sold pursuant to a 10b5-1 trading plan.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of restricted stock units.

The shares were sold pursuant to a 10b5-1 trading plan.

Represents the grant of restricted stock units ("RSUs"). One-half of the shares subject to the RSUs vest on the first anniversary of the grant date and the remainder vest quarterly thereafter evenly.

The shares were sold pursuant to a 10b5-1 trading plan.

The shares were sold at prices ranging from $45.01 to $45.56. The reporting person will provide upon request to the SEC, the issuer or security holder of the issuer, full information regarding the number of shares sold at each separate price.

Represents shares withheld by the Issuer to satisfy the exercise price related obligations in connection with the exercise of the options reported herein.

Each share of Class B Common Stock is convertible into one share of Class A Common Stock at the option of the holder and has no expiration date.

On March 9, 2026, the Reporting Person exercised stock options regarding 33,352 shares of Class B Common Stock (the "Exercise"). Under the terms of the Exercise, the Reporting received 33,352 shares of Class A Common Stock rather than Class B Common Stock. This report reflects the Exercise as the exempt disposition of the stock options, a deemed exempt acquisition of the underlying Class B Common Stock, and a deemed exempt conversion of such Class B Common Stock into Class A Common Stock.

On March 9, 2026, the Reporting Person exercised stock options regarding 33,352 shares of Class B Common Stock (the "Exercise"). Under the terms of the Exercise, the Reporting received 33,352 shares of Class A Common Stock rather than Class B Common Stock. This report reflects the Exercise as the exempt disposition of the stock options, a deemed exempt acquisition of the underlying Class B Common Stock, and a deemed exempt conversion of such Class B Common Stock into Class A Common Stock.

The shares subject to the option are immediately exercisable. One-fourth of the shares subject to the option award vested on October 29, 2017, and thereafter one-forty-eighth of the shares subject to the option award vested monthly.

Each share of Class B Common Stock is convertible into one share of Class A Common Stock at the option of the holder and has no expiration date.

On March 9, 2026, the Reporting Person exercised stock options regarding 33,352 shares of Class B Common Stock (the "Exercise"). Under the terms of the Exercise, the Reporting received 33,352 shares of Class A Common Stock rather than Class B Common Stock. This report reflects the Exercise as the exempt disposition of the stock options, a deemed exempt acquisition of the underlying Class B Common Stock, and a deemed exempt conversion of such Class B Common Stock into Class A Common Stock.

Each share of Class B Common Stock is convertible into one share of Class A Common Stock at the option of the holder and has no expiration date.

On March 9, 2026, the Reporting Person exercised stock options regarding 33,352 shares of Class B Common Stock (the "Exercise"). Under the terms of the Exercise, the Reporting received 33,352 shares of Class A Common Stock rather than Class B Common Stock. This report reflects the Exercise as the exempt disposition of the stock options, a deemed exempt acquisition of the underlying Class B Common Stock, and a deemed exempt conversion of such Class B Common Stock into Class A Common Stock.

The shares were sold pursuant to a 10b5-1 trading plan.

The shares were sold pursuant to a 10b5-1 trading plan.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of PSUs.

These shares of common stock were withheld by the Issuer to satisfy tax withholding obligations associated with the vesting of PSUs.