Gray Media, Inc.

Item 1.01 Entry into a Material Definitive Agreement. On June 29, 2026, Gray Media, Inc. (“Gray” or the “Company”) entered into a purchase agreement (the “Purchase Agreement”) with certain accredited investors (collectively, the “Purchasers”), pursuant to which the Company agreed to sell to the Purchasers, in a private placement transaction (the “Offering”), $70.0 million aggregate principal amount of its 7.250% Senior Secured First Lien Notes due 2033 (the “Additional Notes”). Pursuant to the Purchase Agreement, on June 30, 2026, Gray issued the Additional Notes to the Purchasers. The Additional Notes were issued pursuant to a supplemental indenture (the “Supplemental Indenture”), dated as of June 30, 2026, to that certain indenture, dated as of July 25, 2025, between Gray, the guarantors party thereto and U.S. Bank Trust Company, National Association, as trustee and collateral agent (the “Trustee”) (the “Base Indenture” and, together with the Supplemental Indenture, the “Indenture”). The Additional Notes were issued at 100.000% of par plus accrued interest from and including February 15, 2026. The Additional Notes were offered and sold in a private transaction in reliance on an exemption from the registration requirements under Section 4(a)(2) of the Securities Act of 1933, as amended (the “Securities Act”), and the provisions of Regulation D thereunder. A copy of the Form of Note Purchase Agreement is attached to this Current Report on Form 8-K (this “Current Report”) as Exhibit 10.1 and is incorporated by reference herein. The foregoing description of the Purchase Agreement is qualified in its entirety by reference to the complete text of the Form of Note Purchase Agreement. The Additional Notes are part of the same issuance of, and rank equally and form a single series with, the currently outstanding $775.0 million aggregate principal amount of the Company’s 7.250% Senior Secured First Lien Notes due 2033 (the “Existing Notes” and, together with the Additional Notes, the “Notes”), which were issued in July 2025. The Additional Notes have substantially identical terms to the Existing Notes. The proceeds of the Additional Notes were used to: (i) fund $40.0 million in purchase price consideration for the first closing under Gray’s acquisition of American Spirit Media, LLC described in Item 8.01 below and (ii) fund Gray’s repurchase of an aggregate of 50,000 shares of Series A Perpetual Preferred Stock of the Company (“Series A Perpetual Preferred Stock”) having an aggregate liquidation preference of $50.0 million for a total purchase price of $30.0 million plus accrued but unpaid dividends. The terms of the Notes are governed by the Indenture. The Indenture contains covenants that limit the ability of the Company and any guarantors to, among other things, (i) incur additional indebtedness; (ii) pay dividends on or make distributions in respect of capital stock or make certain other restricted payments or investments; (iii) enter into certain transactions with affiliates of the Company; (iv) enter into certain transactions that restrict distributions from restricted subsidiaries; (v) sell or otherwise dispose of assets; (vi) create or incur liens; merge, consolidate or sell all or substantially all of the Company’s assets; (vii) place restrictions on the ability of subsidiaries to pay dividends or make other payments to the Company; and (viii) designate the Company’s subsidiaries as unrestricted subsidiaries. These covenants are subject to a number of important exceptions and qualifications. The Indenture contains customary events of default, including, among other things, (i) failure to make required payments; (ii) failure to comply with certain agreements or covenants; (iii) failure to pay certain other indebtedness; (iv) certain events of bankruptcy and insolvency; and (v) failure to pay certain judgments. An event of default under the Indenture will allow either the Trustee or the holders of at least 25% in aggregate principal amount of the then-outstanding series of notes, as applicable, issued under such Indenture to accelerate, or in certain cases, will automatically cause the acceleration of, the amounts due under the applicable series of notes. The Notes mature on August 15, 2033. Interest accrues on the Notes from July 25, 2025, and is payable semiannually, on February 15 and August 15 of each year. We may redeem some or all of the Notes at any time after August 15, 2028 at redemption prices specified in the Indenture. We may also redeem up to 40% of the aggregate principal amount of the Notes at 107.250% prior to August 15, 2028 using the net cash proceeds from certain equity offerings, provided, however, that at least 60% of the aggregate principal amount of the Notes originally issued on July 25, 2025 remains outstanding immediately after such redemption. In addition, we may redeem some or all of the Notes at any time prior to August 15, 2028 at a price equal to 100% of the principal amount thereof, plus accrued and unpaid interest, if any, to the redemption date, plus a make whole premium set forth in the Indenture. Prior to August 15, 2028, we may redeem up to 10% of the original principal amount of the Notes (including any additional notes) in any calendar year commencing with the calendar year in which the issue date occurs (but no more than three times in total), at a price equal to 103% of the aggregate principal amount thereof plus accrued and unpaid interest thereon, if any, to, but not including, the redemption date. If we sell certain of our assets or experience specific kinds of changes of control, we must offer to repurchase the Notes. The Notes and related guarantees are Gray’s and the guarantors’ senior secured first lien obligations. The Notes and guarantees: rank pari passu in right of payment to all of Gray’s and the guarantors’ existing and future senior, unsubordinated debt; are senior in right of payment to all of Gray’s and the guarantors’ future subordinated debt; are effectively subordinated to any of Gray’s or the guarantors’ existing and future debt that is secured by a lien on any assets not constituting collateral to the extent of the value of such assets; rank pari passu in right of security with all of Gray’s existing and future debt that is secured by a first priority lien on the collateral; and are effectively senior to all existing and future debt that is either unsecured or secured by a lien that is junior to the lien securing the Notes and the guarantees, in each case to the extent of the value of the collateral. A copy of the Supplemental Indenture is attached to this Current Report as Exhibit 4.2 and is incorporated by reference herein. The Base Indenture and the Form of Notes have been previously filed with the SEC as Exhibits 4.1 and 4.2, respectively, to Gray’s Current Report on Form 8-K filed on July 25, 2025 and are incorporated by reference as if fully set forth within. The foregoing description of the Notes and the Indenture is qualified in its entirety by reference to the complete text of the Indenture.

Item 2.03 Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information contained in Item 1.01 above is hereby incorporated by reference.

Item 7.01 Regulation FD Disclosure. Notes Offering On July 1, 2026, Gray issued a press release announcing the sale and issuance of the Additional Notes. A copy of the press release announcing the sale and issuance of the Additional Notes is attached hereto as Exhibit 99.1 and incorporated herein by reference. Acquisition of American Spirit Media On July 1, 2026, Gray issued a press release announcing the ASM transaction (described in Item 8.01 below). A copy of the press release announcing the ASM transaction is attached hereto as Exhibit 99.2 and incorporated herein by reference. The information set forth under this Item 7.01 is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, except as may be expressly set forth by specific reference in such filing.

Item 8.01 Other Events. Acquisition of American Spirit Media On July 1, 2026, Gray announced that certain subsidiaries and affiliates of Gray had entered into a definitive agreement with American Spirit Media, LLC (“ASM”) to acquire its six television stations for $50.0 million in cash. On July 1, 2026, Gray and ASM completed the first of two closings of the ASM transaction through which, among other things, Gray paid $40.0 million to ASM and commenced a limited local management agreement for the stations. Repurchase of Series A Perpetual Preferred Stock On July 1, 2026, Gray announced that it repurchased, using a portion of the proceeds from the Offering, 50,000 shares of its Series A Perpetual Preferred Stock, having an aggregate liquidation preference of $50.0 million for a total purchase price of $30.0 million plus accrued and unpaid dividends.