Diamond Estates Wines & Spirits Announces Further Replacement of Previously Issued Convertible Debentures

Niagara-on-the-Lake, Ontario--(Newsfile Corp. - December 16, 2025) - Diamond Estates Wines & Spirits Inc. (TSXV: DWS) ("Diamond Estates" or the "Company") announces the replacement of $4,654,000 aggregate principal amount of 10.0% unsecured convertible debentures of the Company (the "2024 Replacement Debentures"), which includes (i) the $2,850,000 aggregate principal amount of 10.0% unsecured convertible debentures of the Company issued to 3346625 Canada Inc. ("Lassonde Holding"), (ii) the $500,000 aggregate principal amount of 10.0% unsecured convertible debentures of the Company issued to Lassonde Industries Inc. ("Lassonde Industries", a joint actor of Lassonde Holding and together with Lassonde Holding, the "Lassonde Group"), and (iii) the $1,304,000 aggregate principal amount of 10.0% unsecured convertible debentures of the Company issued to Raymond James Ltd. in trust for MacNicol & Associates Asset Management Inc., with new debentures (the "2025 Replacement Debentures") maturing on November 9, 2026, the whole in accordance with the terms of the 2024 Replacement Debentures.

The material terms of the 2025 Replacement Debentures, including their principal amounts, are the same as the 2024 Replacement Debentures, other than: (i) the conversion price, which is now $0.22; and (ii) the maturity date, which is now November 9, 2026.

Lassonde Holding and Lassonde Industries, insiders of the Company, accepted an amendment to their existing debenture holdings by exchanging the 2024 Replacement Debentures for an aggregate of $3,350,000 in principal amount of 2025 Replacement Debentures, which are subject to a four month and one day hold period from the date of issuance in accordance with Canadian securities laws. The issuance of the 2025 Replacement Debentures to such insiders (the "Insider Issuance") may be considered related party transactions within the meaning of TSXV Policy 5.9 and Multilateral Instrument 61-101 - Protection of Minority Security Holders in Special Transactions ("MI 61 101"). As the Company's securities are listed on the TSX Venture Exchange ("TSXV"), the Insider Issuance is exempt from the formal valuation requirements of MI 61-101 pursuant to subsection 5.5(b) of MI 61-101. The Insider Issuance was, however, approved by a simple majority of the disinterested shareholders at the Company's annual general and special meeting of shareholders on October 30, 2025, and is subject to the final approval of the TSXV.