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SCHEDULE 13D/A 0000950170-25-036537 0001607278 XXXXXXXX LIVE 2 Common Stock, par value $0.001 04/18/2025 false 0001448431 68401U204 OptimizeRx Corporation 260 CHARLES STREET SUITE 302 WALTHAM MA 02453 David Atterbury (913) 951-2700 Whetstone Capital Advisors, LLC 2001 Shawnee Mission Pkwy Mission Woods KS 66205 0001607278 N Whetstone Capital Advisors, LLC AF N KS 1508303 1508303 1508303 N 8.2 IA OO Y David Atterbury AF N X1 1508303 1508303 1508303 N 8.2 HC IN Common Stock, par value $0.001 OptimizeRx Corporation 260 CHARLES STREET SUITE 302 WALTHAM MA 02453 This Amended No 2. to the Schedule 13D (this "Amendment") that relates to the Common Stock, par value $0.001 (the "Common Stock") of OptimizeRx Corporation, a Nevada corporation (the "Issuer"). The address of the Issuer's principal executive offices is 260 Charles Street, Suite 302, Waltham, MA 02453. This Amendment amends and restates the Schedule 13D filed by the Reporting Persons on February 5, 2025, as subsequently amended on March 10, 2025 (together, the "Schedule 13D"). This Amendment is being filed by Whetstone Capital Advisors, LLC ("WCA") and Mr. David Atterbury (together, the "Reporting Persons"). The principal business addresses of the Reporting Persons are as follows: 2001 Shawnee Mission Pkwy Mission Woods, KS 66205 WCA is a Kansas limited liability company and Mr. David Atterbury is the manager of WCA. WCA serves as the investment advisor to certain private investment funds (the "Funds"), which hold Common Stock of the Issuer, and may direct the vote and disposition of the Common Stock held by the Funds. As the manager of WCA, Mr. Atterbury may direct the vote and disposition of the Common Stock held by the Funds. During the last five years, neither the Reporting Persons (or a controlling entity thereof) nor any executive officer or director of any of the Reporting Persons (or a controlling entity thereof) has been convicted in a criminal proceeding (excluding traffic violations or similar misdemeanors). During the last five years, neither the Reporting Persons (or a controlling entity thereof) nor any executive officer or director of any of the Reporting Persons (or a controlling entity thereof) has been a party to a civil proceeding of a judicial or administrative body of competent jurisdiction. See Item 2(c) above for the place of organization of WCA. Mr. Atterbury is a citizen of the United States of America. The Common Stock reported herein as being beneficially owned by the Reporting Persons was purchased using working capital of the Funds. An aggregate of approximately $7,557,310 (excluding brokerage commissions) was used to purchase the Common Stock reported as beneficially owned by the Reporting Persons in this Schedule 13D. This Amendment hereby amends and supplements Item 4 of the Schedule 13D by inserting the following: On April 18, 2025, WCA submitted to the Issuer a conditional withdrawal of its notice of intent to nominate two candidates for election to the Board at the Issuer's 2025 annual meeting of stockholders (the "Conditional Withdrawal"). The Conditional Withdrawal became effective on the same day, following the Issuer's issuance of a press release announcing its intention to appoint a new independent director to its Board prior to the end of 2025. The Conditional Withdrawal followed discussions held between WCA and the Issuer, and was in connection with a number of actions announced by the Issuer regarding Board refreshment and future strategy. The Reporting Persons intend to review their investments in the Issuer on a continuing basis. Depending on various factors, including, without limitation, the Issuer's financial position and strategic direction, the outcome of the discussions and matters referenced above, actions taken by the Issuer's management or Board, price levels of the Common Stock, liquidity requirements and other investment opportunities available to the Reporting Persons, conditions in the securities market and general economic and industry conditions, the Reporting Persons may in the future take actions with respect to their investment position in the Issuer as they deem appropriate, including, without limitation, purchasing additional shares of Common Stock or other instruments that are based upon or relate to the value of the Common Stock or the Issuer in the open market or otherwise, selling some or all of the securities reported herein, and/or engaging in hedging or similar transactions with respect to the shares of Common Stock. See rows (11) and (13) of the cover pages to this Schedule 13D for the aggregate number of shares of Common Stock and percentage of the Common Stock beneficially owned by each of the Reporting Persons. The percentages reported in this Schedule 13D were calculated based upon the 18,490,385 shares of Common Stock issued and outstanding as of March 11, 2025, as reported in the Issuer's Annual Report on Form 10-K filed with the Securities and Exchange Commission (the "SEC") on March 20, 2025. See rows (7) through (10) of the cover pages to this Schedule 13D for the number of shares of Common Stock as to which each Reporting Person has the sole or shared power to vote or direct the vote and sole or shared power to dispose or to direct the disposition. There were no transactions effected by the Reporting Persons in the Common Stock of the Issuer during the past sixty (60) days. Other than the Funds and the Reporting Persons, no other person is known to have the right to receive, or the power to direct the receipt of, dividends from or proceeds from the sale, of the Common Stock. Not applicable. There are no contracts, arrangements, understandings or relationships (legal or otherwise) among any Reporting Person or between such persons and any person with respect to any securities of the Issuer, including any class of the Issuer's securities used as a reference security, in connection with any of the following: call options, put options, security-based swaps or any other derivative securities, transfer or voting of any of the securities, finder's fees, joint ventures, loan or option arrangements, guarantees of profits, division of profits or loss, or the giving or withholding of proxies. Whetstone Capital Advisors, LLC /s/ David Atterbury David Atterbury, Manager 04/21/2025 David Atterbury /s/ David Atterbury David Atterbury 04/21/2025