Charlotte's Web Holdings, Inc.

Why am I receiving these materials?

Management of the Company is using this proxy statement to solicit proxies for use at the Meeting to be held via live webcast on May 28, 2026.

The following proxy materials are being posted online to access, rather than being mailed out: (1) proxy statement; (2) the Proxy Instrument; (3) the Company’s Annual Report on Form 10-K for the year ended December 31, 2025 (including our audited annual consolidated financial statements of the Company for the fiscal year ended December 31, 2025, together with the notes thereto, and the independent auditor’s report thereon and the related management’s discussion and analysis); and (4) a request for financial statement form for the fiscal year ended December 31, 2026. As permitted by applicable securities law, the Company is using notice-and-access to deliver the proxy materials to shareholders.

As a shareholder, you are invited to attend the Meeting and are entitled and requested to vote on the business items described in this proxy statement. This proxy statement is furnished in connection with the solicitation of proxies by or on behalf of management of the Company. This proxy statement is designed to assist you in voting your shares and includes information that we are required to provide under the rules of the SEC and applicable Canadian securities laws.

These proxy materials are being sent to both registered and non-registered shareholders. In some instances, the Company has distributed copies of the Notice, the proxy statement, the accompanying Proxy Instrument and the Company’s Annual Report on Form 10-K (collectively, the “Documents”) to clearing agencies, securities dealers, banks and trust companies, or their nominees (collectively “Intermediaries”, and each an “Intermediary”) for onward distribution to shareholders whose shares are held by or in the custody of those Intermediaries (“Non-registered Shareholders”). Subject to below, the Intermediaries are required to forward the Documents to Non-registered Shareholders.

In accordance with applicable laws, Non-registered Shareholders who have advised their Intermediary that they do not object to the Intermediary providing their ownership information to issuers whose securities they beneficially own (“NOBOs”) will receive by mail a letter with respect to the Notice of Internet Availability of Proxy Materials. NOBOs who have standing instructions with the Intermediary for physical copies of this proxy statement will receive by mail the Notice of Internet Availability of Proxy Materials, the Notice and the proxy statement.

Management of the Company intends to pay for Intermediaries to forward the Notice of Internet Availability of Proxy Materials to Non-Registered Holders who have advised their Intermediary that they object to the Intermediary providing their ownership information (“OBOs”).

Solicitation of proxies from Non-registered Shareholders will be carried out by Intermediaries, or by the Company if the names and addresses of Non-registered Shareholders are provided by the Intermediaries.

Non-registered Shareholders who have received the Documents from their Intermediary should follow the directions of their Intermediary with respect to the procedure to be followed for voting at the Meeting. Generally, Non-registered Shareholders will either:

•receive a form of proxy executed by the Intermediary but otherwise uncompleted. The Non-registered Shareholder may complete the proxy and return it directly to Broadridge Financial Solutions, Inc. (“Broadridge”); or

•be provided with a request for voting instructions. The Intermediary is required to send the Company an executed form of proxy completed in accordance with any voting instructions received by the Intermediary.

If you are a Non-registered Shareholder and the Company or its agent has sent these materials directly to you, your name and address and information about your holdings of securities have been obtained from your Intermediary in accordance with applicable securities regulatory requirements. By choosing to send the Documents to you directly, the Company (and not your Intermediary) has assumed responsibility for: (i) delivering the Documents to you; and (ii) executing your proper voting instructions. Non-registered Shareholders who have elected to receive the Documents by electronic delivery (“e-Delivery”) will have received e-mail notification from the Intermediary that the Documents are available electronically on the Company’s website. Please return your voting instructions as specified in the request for voting instructions.

Receiving Future Meeting Materials by Email

e-Delivery ensures that shareholders receive documents faster, helps reduce printing and postage expenses and creates less paper waste. Shareholders who wish to enroll in e-Delivery may sign up at www.proxyvote.com.

What is included in the proxy materials?

The proxy materials include:

•our Notice of Meeting;

•our proxy statement for the Meeting (including a copy of our Annual Benefit Report for the year ended December 31, 2025);

•a Proxy Instrument or voting instruction card;

•our 2025 Annual Report on Form 10-K (including the audited annual consolidated financial statements of the Company for the fiscal year ended December 31, 2025, together with the notes thereto, and the independent auditor’s report thereon and the related management’s discussion and analysis); and

•a request for financial statement form for the fiscal year ended December 31, 2026.

What information is contained in this proxy statement?

The information in this proxy statement relates to the proposals to be voted on at the Meeting, the voting process, our Board and Board committees, corporate governance, the compensation of our directors and executive officers and other required information.

I share an address with another shareholder, and we received only one paper copy of the proxy materials. How may I obtain an additional copy?

If you share an address with another shareholder, you may receive only one set of proxy materials unless you have provided contrary instructions. If you wish to receive a separate set of the materials, please request the additional copy by contacting our Corporate Secretary at legal@charlottesweb.com or by calling us at (720) 484-8930.

A separate set of the materials will be sent promptly following receipt of your request.

If you are a shareholder of record and wish to receive a separate set of proxy materials in the future, or if you have received multiple sets of proxy materials and would like to receive only one set in the future, please contact Broadridge at:

Broadridge

51 Mercedes Way

Edgewood, NY 11717

1-866-540-7095

If you are a Non-registered Shareholder and you wish to receive a separate set of proxy materials in the future, or if you have received multiple sets of proxy materials and would like to receive only one set in the future, please contact your bank or broker directly.

Shareholders also may write to, or email us, at the address below to request a separate copy of the proxy materials:

Attn: Corporate Secretary

Louisville, CO 80027

legal@charlottesweb.com

Who pays the cost of soliciting proxies for the Meeting?

The Company will bear the cost of solicitation, including the cost of preparing, printing and mailing the materials in connection with the solicitation of proxies. This solicitation of proxies is being made to shareholders by mail but may be supplemented by telephone or other personal contact. The Company’s officers and regular employees, on behalf of the Company without being additionally compensated, may solicit proxies personally and by mail, telephone, facsimile or electronic communication at nominal cost to the Company.

The Company will not reimburse Intermediaries such as brokerage houses and other custodians, nominees and fiduciaries for forwarding proxy materials to Non-registered Shareholders.

What items of business will be voted on at the Meeting?

The business items to be voted on at the Meeting are:

•The setting of the number of directors at six;

•The election of directors for the forthcoming year from the nominees proposed by the Board;

•The appointment of PKF O’Connor Davies LLP, as auditors for the Company and the authorization of the Board to fix the auditors’ remuneration and terms of engagement;

•The ordinary resolution (the "Transaction Resolution") authorizing and approving the amendment (the "Amendment") of the Company's C$75,341,080 principal amount convertible debenture held by BT DE Investments Inc. (“BAT”), a wholly owned subsidiary of British American Tobacco p.l.c., issued on November 14, 2022 (the “Convertible Debenture”) and the issuance of common shares of the Company ("Common Shares") that may be required to be issued to BAT upon: (i) the conversion (the “Conversion”) of the Convertible Debenture; and (ii) the concurrent equity investment in the Company by BAT (the “Investment”, and together with the Amendment and the Conversion, the “Transaction”), where such Transaction would, (x) “materially affect control” (as such term is defined in the Toronto Stock Exchange Company Manual) of the Company through the creation of a new “Control Person” (as such term is defined in the Securities Act (British Columbia)); and (y) result in the issuance of greater than 25% of the number of Common Shares issued and outstanding prior to the closing of the Transaction; and

•The transaction of such other business as may properly come before the Meeting or any adjournment(s) or postponement(s) thereof.

What are my voting choices?

You may vote “FOR” or “AGAINST” the setting of the number of directors at six; “FOR” or “WITHHOLD” the election of nominees for election as directors; “FOR” or “WITHHOLD” the appointment of PKF O’Connor Davies LLP; and “FOR” or “AGAINST” the Transaction Resolution, as auditors for the ensuing year and the authorization of the Board to fix the auditor’s remuneration.

How does the Board recommend that I vote?

Our Board recommends that you vote your shares “FOR” the setting of the number of directors at six, “FOR” each of its nominees for election to the Board, “FOR” the appointment of PKF O’Connor Davies LLP as auditors for the ensuing year and the authorization of the Board to fix the auditor’s remuneration, and “FOR” the Transaction Resolution.

What vote is required to approve each item?

To conduct business at the Meeting, the quorum of shareholders is at least two persons who are, or who represent by proxy, shareholders who, in the aggregate, hold at least 25% of the issued shares entitled to be voted at the Meeting.

If you indicate “WITHHOLD” in respect to the election of directors, your vote will be counted for purposes of determining the presence or absence of a quorum for the transaction of business at the Meeting. As described below, broker non-votes will be counted for determining the presence or absence of a quorum for the transaction of business at the Meeting, but will not be considered votes cast with respect to the election of any director nominee or on any other proposal.

*The Board has adopted a “majority voting” policy (the “Majority Voting Policy”). Pursuant to the Majority Voting Policy, if a nominee for election as director receives “for” votes fewer than a majority of the votes (50% + 1 vote) cast with respect to his or her election by shareholders, he or she must immediately tender his or her resignation to the Board following the meeting of shareholders at which the election is held. Upon receiving such resignation, the Corporate Governance and Nominating Committee (the “CG&N Committee”) will consider it and make a recommendation to the Board on whether or not to accept the resignation. The Board shall accept the resignation unless it determines that the applicable director shall continue and announce its decision in a press release promptly within 90 days following the meeting of shareholders. If the Board determines not to accept a resignation, the press release must fully state the reasons for that decision. The resignation will be effective when accepted by the Board. The director who tendered his or her resignation is not permitted to be a part of any deliberations of the CG&N Committee or of the Board pertaining to the resignation offer. The policy only applies in circumstances involving an uncontested election of directors.

** The Transaction Resolution must be approved by a simple majority (50%+1) of the disinterested shareholders of the Company. For purposes of disinterested shareholder approval, to the knowledge of the Company, and assuming the following remains true as of date of the Meeting, the only votes to be excluded will be those held by BAT, which, as at the date hereof, holds nil Common Shares. Abstentions and broker non-votes, if any, will have no effect on the outcome of the proposal. See "Proposal 4 - Amendment of Convertible Debenture and Investment by BT DE Investments Inc." below for more information.

What happens if additional items are presented at the Meeting?

As of the date of this proxy statement, management of the Company knows of no such amendments, variations or other matters to come before the Meeting. However, if other matters properly come before the Meeting, it is the intention of the persons named in the enclosed Proxy Instrument to vote such proxy according to their best judgment.

Where can I find the voting results?

We expect to announce preliminary voting results at the Meeting and to publish final results in a current report on Form 8-K that we will file with the SEC and in a report of voting results in accordance with National Instrument 51-102 –Continuous Disclosure Obligations that we will file in Canada on SEDAR+ promptly following the Meeting. Both the Form 8-K and report on voting results will also be available on the “Investor Relations” section of our website at https://investors.charlottesweb.com.