A copy of this second amended and restated preliminary prospectus has been filed with the securities regulatory authorities in each of the provinces of Canada (other than Qu´ebec) but has not yet become final for the purpose of the sale of securities. Information contained in this second amended and restated preliminary prospectus may not be complete and may have to be amended. The securities may not be sold until a receipt for the prospectus is obtained from the securities regulatory authorities. No securities regulatory authority has expressed an opinion about these securities and it is an offence to claim otherwise. This prospectus constitutes a public offering of securities only in those jurisdictions where such securities may be lawfully offered for sale and therein only by persons permitted to sell such securities. See ‘‘Plan of Distribution’’. These securities have not been and will not be registered under the United States Securities Act of 1933, as amended (the ‘‘U.S. Securities Act’’), or any securities laws of any state of the United States and may not be offered or sold in the United States except in compliance with the registration requirements of the U.S. Securities Act and any applicable state securities laws or pursuant to an applicable exemption therefrom. This prospectus does not constitute an offer to sell or a solicitation of an offer to buy any of the securities offered hereby within the United States. See ‘‘Plan of Distribution’’. SECOND AMENDED AND RESTATED PRELIMINARY PROSPECTUS (amending and restating the amended and restated preliminary prospectus dated July 13, 2018, which amended and restated the preliminary prospectus dated June 25, 2018) Initial Public Offering and Secondary Offering August 22, 2018 12JUL201809040256 CHARLOTTE’S WEB HOLDINGS, INC. C$100,100,000 14,300,000 Common Shares This prospectus qualifies the distribution of an aggregate of 14,300,000 common shares (‘‘Common Shares’’) in the capital of Charlotte’s Web Holdings, Inc. (the ‘‘Company’’, ‘‘we’’, ‘‘our’’, ‘‘us’’) consisting of a treasury issuance by the Company of 13,312,150 Common Shares (the ‘‘Treasury Offering’’) and a secondary offering of 987,850 Common Shares (the ‘‘Secondary Base Offering’’, and together with the Treasury Offering, the ‘‘Offering’’) at a price of C$7.00 per Common Share (the ‘‘Offering Price’’). The Company intends to use the net proceeds of the Treasury Offering as described in this prospectus. See ‘‘Use of Proceeds’’. The Common Shares are being offered for sale by Canaccord Genuity Corp. (the ‘‘Lead Underwriter’’), as lead underwriter, GMP Securities L.P., PI Financial Corporation, and Cormark Securities Inc. (collectively, the ‘‘Underwriters’’). If the Over-Allotment Option (as defined below) is exercised in full, an additional 2,145,000 Common Shares will be offered by the Selling Shareholders (as defined below). The Common Shares issued pursuant to the Offering, including those which may be sold pursuant to the Over-Allotment Option, are collectively referred to herein as the ‘‘Offered Shares’’. The Company has been created to indirectly acquire and hold all of the capital stock in CWB Holdings, Inc. (‘‘CWB’’), a market leader in the production and distribution of innovative hemp-based, CBD wellness products. Through its vertically integrated business model, CWB strives to improve customers’ lives and meet their demands for stringent product quality, efficacy and consistency. CWB does not produce or sell medicinal or recreational marijuana or products derived therefrom. Immediately after the closing of the Offering, as part of the Reorganization (as defined below) (collectively, the ‘‘Closing’’), all of the existing securityholders of CWB will exchange their securities of CWB for securities of the Company. See ‘‘Corporate Structure — Reorganization’’. Upon completion of the Offering, the Company’s share capital will consist of two classes of issued and outstanding shares: Common Shares and proportionate voting shares (the ‘‘Proportionate Voting Shares’’) (collectively, the ‘‘Shares’’); and one authorized class of preferred shares issuable in series, none of which will be issued and outstanding. Generally, the Common Shares and Proportionate Voting Shares have the same rights, are equal in all respects and are treated by the Company as if they were shares of one class only. Proportionate Voting Shares, or fractions thereof, may at any time, subject to the FPI Condition, at the option of the holder and subject to certain restrictions, be converted into Common Shares at a ratio of 400 Common Shares per Proportionate Voting Share. Prior to conversion, each Proportionate Voting Share, or fraction thereof, carries 400 votes per share (compared to one vote per Common Share) and is entitled to dividends and liquidation distributions in an amount equal to 400 times the amount distributed in respect of each Common Share. The Common Shares may at any time, at the option of the holder and with the consent of the Company, be converted into Proportionate Voting Shares at a ratio of 400 Common Shares for one Proportionate Voting Share. Upon completion of the Offering and the Reorganization, (continued on next page) CRAFTED IN NATURE. PERFECTED BY SCIENCE. TRUSTED BY FAMILIES. A market leader in the production and distribution of innovative hemp-based, cannabidiol (CBD) wellness products. $40 MILLION 35% 2017 REVENUE 2017 EBITDA MARGIN E-COMMERCE SALES GROWTH 300 ACRES OF CULTIVATION (2018E) 60% FROM 2016 TO 2017 SOLD IN 40,000FT2 MANUFACTURING 2,700 AND R&D FACILITY RETAIL LOCATIONS CAGR OF FAST GROWING SEGMENT 55% $50B OF A ROBUST MARKET HEMP-DERIVED CBD U.S. SUPPLEMENTS SEGMENT (2016-2021) MARKET (2020) REVENUE: (US$ MILLION) GROWTH 2016 $14.7 172% 2017 $40.0 ADJUSTED EBITDA (US$ MILLION) GROWTH 2016 $2.0 600% 2017 $14.1 GROSS EBITDA BRAND BY MARKET MARGIN MARGIN MARKET SHARE SHARE* 80% 34% #1 14% Q1-2018 *2017 management estimate (continued from cover) assuming no exercise of the Over-Allotment Option and excluding the Private Placement (as defined below), the Company will have an aggregate of 14,300,000 Common Shares and 194,178.15 Proportionate Voting Shares issued and outstanding. See ‘‘Description of Share Capital’’ and ‘‘Exemption from National Instruments’’. Upon completion of the Offering and the Reorganization, all of the issued and outstanding Proportionate Voting Shares will be held or controlled, directly or indirectly, by the former CWB Shareholders (as defined below). As a result, the former CWB Shareholders will collectively own or control, directly or indirectly, an equivalent of 77,671,258 Common Shares (assuming the conversion of all Proportionate Voting Shares to Common Shares on the basis of 400 Common Shares for one Proportionate Voting Share), representing an 83.7% equity and voting interest in the Company assuming the Private Placement is fully subscribed (85.7% on a fully-diluted basis), and if the Over-Allotment Option is exercised in full, the former CWB Shareholders, collectively, will own an equivalent of 75,526,258 Common Shares (assuming the conversion of all Proportionate Voting Shares to Common Shares on the basis of 400 Common Shares for one Proportionate Voting Share), representing an 81.4% equity and voting interest in the Company assuming the Private Placement is fully subscribed (83.7% on a fully-diluted basis). Upon completion of the Offering and the Reorganization, and in the event that the Over-Allotment Option is exercised in full and assuming the Private Placement is fully subscribed, the Selling Shareholders, collectively, will own an equivalent of 51,060,538 Common Shares (assuming the conversion of all Proportionate Voting Shares to Common Shares on the basis of 400 Common Shares for one Proportionate Voting Share), representing a 55.0% equity and voting interest in the Company (48.1% on a fully-diluted basis). There is no market through which these securities may be sold, and purchasers may not be able to resell securities purchased under this prospectus. This may affect the pricing of the securities in the secondary market, the transparency and availability of trading prices, the liquidity of the securities and the extent of issuer regulation. An investment in the Offered Shares is speculative and is subject to a number of risks that should be considered by a prospective purchaser. Prospective purchasers should carefully consider the risk factors described under ‘‘Risk Factors’’ before purchasing the Offered Shares. The Canadian Securities Exchange (the ‘‘CSE’’) has conditionally approved the listing of the Common Shares under the symbol ‘‘CWEB’’. Listing is subject to fulfilling all of the requirements of the CSE on or before ɀ , 2018. As of the date of this prospectus, the Company does not have any of its securities listed or quoted, has not applied to list or quote any of its securities, and does not intend to apply to list or quote any of its securities, on the Toronto Stock Exchange, Aequitas NEO Exchange Inc., any U.S. marketplace, or a marketplace outside Canada and the United States of America. Price: C$7.00 per Offered Share(1) Price to Net Proceeds to the Underwriters’ Net Proceeds to Selling Public Fee(3) the Company(2) Shareholders(5) Per Offered Share C$7.00 C$0.42 C$6.58 C$6.58 Total Offering(2)(4) C$100,100,000 C$6,006,000 C$87,593,947 C$6,500,053 Notes: (1) The Offering Price of the Offered Shares was determined through negotiations between the Company and the Underwriters. The Offering Price may not be indicative of the market price of the Common