High Roller Technologies, Inc.

Item 5. OTHER INFORMATION

RULE 10b5-1 TRADING ARRANGEMENT

Insider Trading Arrangements

On May 14, 2026, Adam Felman, the Company's Chief Financial Officer, adopted a written trading arrangement for the sale of shares of the Company's common stock that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c) under the Securities Exchange Act of 1934, as amended (a "Rule 10b5-1 trading arrangement"). The arrangement provides for the sale of up to 61,200 shares of common stock in the aggregate and terminates on the earlier of May 19, 2027 and the date on which all shares subject to the arrangement have been sold.

The shares subject to the arrangement consist of up to 16,800 shares in respect of performance-based equity awards and up to 14,400 shares in respect of time-based equity awards, which shares were intended, at the time of adoption, to fund tax withholding obligations arising from the vesting of such awards. In addition, up to 30,000 shares are available to be sold upon the achievement of specified price thresholds set forth in the arrangement. The number of shares actually sold in respect of the equity awards will depend on the market price of the common stock on the applicable vesting dates and the applicable withholding rates, and may differ from the amounts set forth above.

Other than as described above, during the three months ended June 30, 2026, no director or officer of the Company adopted orterminated a Rule 10b5-1 trading arrangement or any written trading arrangement that meets the requirements of a "non-Rule 10b5-1 trading arrangement" as defined in Item 408(c) of Regulation S-K.