RYAN · Ryan Specialty Holdings, Inc. · Insider Trading

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were sold in multiple transactions ranging from $40.47 to $40.67, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock sold at each separate price in the ranges set forth in this footnote.

Shares of Class B Common Stock, par value $0.001 per share, ("Class B Common Stock") do not represent economic interests in the Issuer. Except as provided in the Issuer's certificate of incorporation or as required by applicable law, holders of Class B Common Stock will be initially entitled to 10 votes per share on all matters to be voted on by the Issuer's stockholders generally. Upon exchange of Common Units ("Common Units") of New Ryan Specialty, LLC that are held by the Reporting Person and reported in Table II hereof, for an equal number of shares of Class A Common Stock, par value $0.001 per share, ("Class A Common Stock") of the Issuer, an equal number of shares of the Issuer's Class B Common Stock will be cancelled for no consideration.

Pursuant to the Amended and Restated Limited Liability Company Agreement of New Ryan Specialty, LLC, as amended, the reporting person may exchange all or a portion of such person's Common Units of the LLC (together with the delivery of an equal number of shares of Class B Common Stock of the Issuer) for shares of Class A Common Stock of the Issuer on a one-for-one basis, subject to customary adjustments, or, at the option of the Issuer, cash (based on the then-market value of the Class A Common Stock). The Common Units do not expire.

Transfer to the Reporting Person's spouse in connection with a negotiation of separation of assets in anticipation of a potential divorce settlement.

Pursuant to the Amended and Restated Limited Liability Company Agreement of New Ryan Specialty, LLC, as amended, the reporting person may exchange all or a portion of such person's Common Units of the LLC (together with the delivery of an equal number of shares of Class B Common Stock of the Issuer) for shares of Class A Common Stock of the Issuer on a one-for-one basis, subject to customary adjustments, or, at the option of the Issuer, cash (based on the then-market value of the Class A Common Stock). The Common Units do not expire.

Shares of Class B Common Stock, par value $0.001 per share, ("Class B Common Stock") do not represent economic interests in the Issuer. Except as provided in the Issuer's certificate of incorporation or as required by applicable law, holders of Class B Common Stock will be initially entitled to 10 votes per share on all matters to be voted on by the Issuer's stockholders generally. Upon exchange of Common Units ("Common Units") of New Ryan Specialty, LLC that are held by the Reporting Person and reported in Table II hereof, for an equal number of shares of Class A Common Stock, par value $0.001 per share, ("Class A Common Stock") of the Issuer, an equal number of shares of the Issuer's Class B Common Stock will be cancelled for no consideration.

Transfer to the Reporting Person's spouse in connection with a negotiation of separation of assets in anticipation of a potential divorce settlement.

Shares of Class B Common Stock, par value $0.001 per share, ("Class B Common Stock") do not represent economic interests in the Issuer. Except as provided in the Issuer's certificate of incorporation or as required by applicable law, holders of Class B Common Stock will be initially entitled to 10 votes per share on all matters to be voted on by the Issuer's stockholders generally. Upon exchange of Common Units ("Common Units") of New Ryan Specialty, LLC that are held by the Reporting Person and reported in Table II hereof, for an equal number of shares of Class A Common Stock, par value $0.001 per share, ("Class A Common Stock") of the Issuer, an equal number of shares of the Issuer's Class B Common Stock will be cancelled for no consideration.

Transfer to the Reporting Person's spouse in connection with a negotiation of separation of assets in anticipation of a potential divorce settlement.

Transfer to the Reporting Person's spouse in connection with a negotiation of separation of assets in anticipation of a potential divorce settlement.

Pursuant to the Amended and Restated Limited Liability Company Agreement of New Ryan Specialty, LLC, as amended, the reporting person may exchange all or a portion of such person's Common Units of the LLC (together with the delivery of an equal number of shares of Class B Common Stock of the Issuer) for shares of Class A Common Stock of the Issuer on a one-for-one basis, subject to customary adjustments, or, at the option of the Issuer, cash (based on the then-market value of the Class A Common Stock). The Common Units do not expire.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were sold in multiple transactions ranging from $42.26 to $42.28, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock sold at each separate price in the ranges set forth in this footnote.

The reporting person disclaims beneficial ownership except to the extent of his pecuniary interest therein.

The stock options vest in equal amounts on October 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

The stock options vest in equal amounts on October 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

On August 4, 2026, the reporting person, as trustee of Ryan Stock Option Trust, dated April 28, 2026 (The "Trust"), entered into Amendment No. 1 to Executive Chairman Option Settlement Agreement (the "Amendment") with Ryan Specialty Holdings, Inc. (the "Issuer"), pursuant to which the Trust has the obligation to sell to the Issuer an aggregate of up to an additional 287,646 shares of Class A common stock from time to time through September 9, 2036. The Amendment was entered into in connection with the Issuer's grant of compensatory Executive Chairman Stock Options to certain employees under the Issuer's 2021 Omnibus Incentive Plan, which stock options vest in equal annual installments on October 1, 2029, 2030 and 2031. The Issuer will exercise its right to purchase shares from the Trust at such times and in such amounts as the corresponding employee stock options are exercised following vesting.

By reporting person, as trustee of Ryan Stock Option Trust, dated April 28, 2026 (the "Trust"), which was formed for the sole purpose of holding the shares of Class A common stock subject to the Amendment described in footnote (1) as well as the Class A common stock subject to the underlying Executive Chairman Option Settlement Agreement. On August 4, 2026, the reporting person transferred 287,646 shares of Class A common stock to the Trust in an exempt transaction pursuant to Rule 16a-13.

The Restricted LLC Units of New Ryan Specialty, LLC (the "LLC") vested and, at the option of the Issuer, settled into shares of Class A common stock of the Issuer.

Represents Restricted LLC Units of New Ryan Specialty, LLC granted on July 22, 2021 which vest 10% each year on the anniversary of the grant date from July 22, 2024 to July 22, 2030 and 30% on July 22, 2031. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3). Each Restricted LLC Unit represents a contingent right to receive one Common Unit and one share of Class B Common Stock. The Common Units are exchangeable on a one-for-one basis for Class A Common Stock of the Issuer.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were purchased in multiple transactions ranging from $35.57 to $35.94, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock purchased at each separate price in the ranges set forth in this footnote.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were purchased in multiple transactions ranging from $34.56 to $35.06, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock purchased at each separate price in the ranges set forth in this footnote.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were purchased in multiple transactions ranging from $35.15 to $35.165, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock purchased at each separate price in the range set forth in this footnote.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were purchased in multiple transactions ranging from $32.24 to $32.62, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock purchased at each separate price in the ranges set forth in this footnote.

By reporting person and spouse, as co-trustees of the Patrick G. Ryan Living Trust dated July 10, 2001 and the Shirley W. Ryan Living Trust dated July 10, 2001.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were purchased in multiple transactions ranging from $31.0550 to $31.0694, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock purchased at each separate price in the range set forth in this footnote.

The price reported is a weighted average price. These shares of Class A Common Stock of the Issuer were purchased in multiple transactions ranging from $31.17 to $32.13, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Class A Common Stock purchased at each separate price in the range set forth in this footnote.

The reporting person disclaims beneficial ownership except to the extent of his pecuniary interest therein.

The shares gifted on May 28, 2026 were gifted to the reporting persons trust (Henry S. Bienen 1997 Trust Dated November 10, 1997).

The reporting person disclaims beneficial ownership except to the extent of his pecuniary interest therein.

The shares gifted on May 28, 2026 were gifted to the reporting persons trust (Henry S. Bienen 1997 Trust Dated November 10, 1997).

The stock options vest in equal amounts on July 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

The stock options vest in equal amounts on July 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

The stock options vest in equal amounts on July 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

The stock options vest in equal amounts on July 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

On May 5, 2026, the reporting person, as trustee of Ryan Stock Option Trust, dated April 28, 2026 (The "Trust"), entered into the Executive Chairman Option Settlement Agreement (the "Agreement") with Ryan Specialty Holdings, Inc. (the "Issuer"), pursuant to which the Trust has the obligation to sell to the Issuer an aggregate of up to 1,787,446 shares of Class A common stock from time to time through June 10, 2036. The Agreement was entered into in connection with the Issuer's grant of compensatory Executive Chairman Stock Options to certain employees under the Issuer's 2021 Omnibus Incentive Plan, which stock options vest in equal annual installments on July 1, 2029, 2030 and 2031. The Issuer will exercise its right to purchase shares from the Trust at such times and in such amounts as the corresponding employee stock options are exercised following vesting.

By reporting person, as trustee of Ryan Stock Option Trust, dated April 28, 2026 (the "Trust"), which was formed for the sole purpose of holding the shares of Class A common stock subject to the Agreement described in footnote (1). On May 4, 2026, the reporting person transferred 1,787,446 shares of Class A common stock to the Trust, which transfer was a nonreportable change in form pursuant to Rule 16a-13.

The stock options vest in equal amounts on July 1, 2029, 2030 and 2031 and are exercisable on a 1-for-1 basis for shares of Class A common stock, par value $0.001 per share, of the Issuer. Such grant was approved by the compensation and governance committee of the board of the Issuer for the purposes of rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

Includes 8,080 Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The reported securities represent Restricted Stock Units that vested immediately upon grant. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

Includes 20,580 Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

Includes 15,270 Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

The reported securities represent Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors. Such grant was approved by the Board of the Issuer for purposes of Rule 16(b)(3).

Includes 16,219 Restricted Stock Units that vested immediately upon grant for which the reporting person has elected to defer settlement until their separation from service on the board of directors.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A Common Stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in five equal annual installments beginning April 1, 2025.

These shares were withheld to pay tax withholding obligations upon the vesting of of the restricted stock units.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A Common Stock of Ryan Specialty Holdings, Inc.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A common stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in three equal annual installments beginning on April 1, 2029.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A common stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in three equal annual installments beginning on April 1, 2029.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A common stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in three equal annual installments beginning on April 1, 2029.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A common stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in three equal annual installments beginning on April 1, 2029.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A common stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in three equal annual installments beginning on April 1, 2029.

Each Restricted Stock Unit represents a contingent right to receive on vesting one share of Class A common stock of Ryan Specialty Holdings, Inc.

The Restricted Stock Units vest in three equal annual installments beginning on April 1, 2029.