SCHEDULE: High Roller Technologies Ownership Update

Cascadia Holdings Ltd distributed 787,648 shares of High Roller Technologies common stock to Jeff Smith, resulting in his departure from the reporting group.

Summary

• Cascadia Holdings Ltd executed a share redemption agreement with Jeff Smith on April 28, 2026.
• The agreement involved the distribution of 787,648 shares of High Roller Technologies common stock to Mr. Smith.
• Following this distribution, Jeff Smith is no longer a beneficial owner of the shares held by Cascadia and has relinquished shared voting and dispositive power.
• Brandon Eachus and Michael Cribari continue to report beneficial ownership of approximately 24.9% and 24.5% of the company, respectively.

Sentiment

Score: 5

Explanation: StockSavvy.ai views this as a neutral administrative update regarding internal ownership distribution rather than a fundamental change in the company's business operations.

Positives

• The distribution clarifies the ownership structure and removes Jeff Smith from the reporting group, simplifying the beneficial ownership profile.

Negatives

• The distribution of shares to a former partner may increase the number of shares held by an individual who is no longer part of the core reporting group.

Risks

• Potential market volatility if the distributed shares are liquidated by the recipient.
• Concentration of ownership remains high among the remaining reporting persons.

Future Outlook

No specific future operational guidance provided; the filing is strictly related to changes in beneficial ownership.

Industry Context

StockSavvy.ai notes that changes in Schedule 13D filings regarding major shareholders often signal internal restructuring or liquidity events for private holding entities, which can precede changes in market sentiment regarding the issuer's stock.

Comparison to Industry Standards

• The filing follows standard SEC disclosure requirements for significant changes in beneficial ownership (greater than 5% threshold).
• The use of a share redemption agreement to settle interests in a holding company is a common practice in private equity and investment holding structures.

Corporate Governance

Related Party Transactions

• Distribution of 787,648 shares of common stock to Jeff Smith pursuant to a share redemption agreement with Cascadia Holdings.

Stakeholder Impact

• Shareholders may see a change in the concentration of voting power among the remaining reporting persons.

Next Steps

• Monitoring of future Form 4 filings by Jeff Smith to see if the distributed shares are sold.

Key Dates

Keywords

High Roller Technologies, Schedule 13D, Cascadia Holdings, Beneficial Ownership, Share Redemption, Equity Distribution