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Cascadia Holdings reshapes High Roller (ROLR) stake with 787,648-share distribution

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Cascadia Holdings Ltd, a reporting person for High Roller Technologies, Inc., reported an internal restructuring of its position in the company. Cascadia distributed 787,648 shares of common stock of High Roller Technologies to one of its own shareholders for no additional consideration under a share redemption agreement.

After this change, Cascadia reports 1,800,748 shares of common stock held directly and maintains indirect joint beneficial ownership of additional shares through entities including Spike Up Media A.B. and Spike Up Media LLC. It also indirectly holds a warrant with an exercise price of $2.37 per share, exercisable for common stock until June 30, 2027. The filing reflects ownership reallocation rather than open‑market buying or selling of ROLR shares.

Positive

  • None.

Negative

  • None.
Insider Cascadia Holdings Ltd
Role null
Type Security Shares Price Value
Other Common Stock 787,648 $0.00 --
holding Warrant (right to buy) -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Common Stock — 1,800,748 shares (Direct, null); Warrant (right to buy) — 39,712 shares (Indirect, See footnote); Common Stock — 731,388 shares (Indirect, See footnote)
Footnotes (1)
  1. Cascadia Holdings Ltd. ("Cascadia") distributed 787,648 shares of common stock of High Roller Technologies, Inc. ("Company") to one of its shareholders, pro rata to his interest for no additional consideration, pursuant to share redemption agreement between that shareholder and Cascadia. Includes indirect joint beneficial ownership of 731,388 shares of common stock held by Spike Up Media A.B. ("Spike Up AB") and 39,172 shares of common stock issuable upon exercise of a warrant of the Issuer held by Spike Up Media LLC ("Spike Up LLC"). Spike Up LLC is a wholly owned indirect subsidiary of Spike Up A.B., which is a wholly owned subsidiary of Ellmount Interactive A. B. ("Interactive"). Cascadia and OEH Invest AB ("OEH") own 66.9% and 33.1% of Interactive, respectively. Michael Cribari and Brandon Eachus as principal shareholders of Cascadia have joint voting and dispositive authority over the shares of Issuer held directly by Cascadia. OEH and Cascadia may be deemed to have joint voting and joint dispositive power over the securities of the Issuer beneficially held by Interactive and a minority shareholder of Cascadia, who has no voting or dispositive power over shares directly held by Cascadia, may be deemed to have a limited pecuniary interest in the shares held indirectly by Interactive.
Restructuring shares 787,648 shares Shares of High Roller common stock distributed under share redemption agreement
Direct holdings after transaction 1,800,748 shares High Roller common stock directly owned by Cascadia after restructuring
Indirectly covered warrant shares 39,712 shares Common stock underlying warrant held indirectly, as per derivative summary
Warrant exercise price $2.37 per share Exercise price of indirectly held warrant on High Roller common stock
Warrant expiration June 30, 2027 Expiration date of the indirectly held High Roller warrant
Indirect common stock holding entry 731,388 shares Indirect joint beneficial ownership of High Roller common stock via Spike Up entities
share redemption agreement financial
"pursuant to share redemption agreement between that shareholder and Cascadia"
indirect joint beneficial ownership financial
"Includes indirect joint beneficial ownership of 731,388 shares of common stock"
warrant (right to buy) financial
"Warrant (right to buy) with an exercise price of $2.37 per share"
dispositive power financial
"have joint voting and dispositive authority over the shares of Issuer"
Dispositive power is the authority to decide the final outcome of an asset, legal claim, contract, or corporate action — in effect the power to dispose of or resolve something. For investors it matters because whoever holds that authority can determine who gets paid, who controls an asset or vote, and how risks and returns are allocated; think of it like holding the key that lets you lock in the winner or loser in a deal.
pecuniary interest financial
"may be deemed to have a limited pecuniary interest in the shares"
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Cascadia Holdings Ltd

(Last)(First)(Middle)
OFFICE 1/5587, LEVEL G, QUANTUM HOUSE
75 ABATE RIGORD STREET

(Street)
TA' XBIEXO1

(City)(State)(Zip)

MALTA

(Country)
2. Issuer Name and Ticker or Trading Symbol
High Roller Technologies, Inc. [ ROLR ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
Officer (give title below)Other (specify below)
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
04/28/2026
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock04/28/2026J(1)787,648D(1)1,800,748D
Common Stock731,388ISee footnote(2)(3)
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Warrant (right to buy)$2.3706/30/202206/30/2027Common Stock39,71239,712ISee footnote(2)(3)
Explanation of Responses:
1. Cascadia Holdings Ltd. ("Cascadia") distributed 787,648 shares of common stock of High Roller Technologies, Inc. ("Company") to one of its shareholders, pro rata to his interest for no additional consideration, pursuant to share redemption agreement between that shareholder and Cascadia.
2. Includes indirect joint beneficial ownership of 731,388 shares of common stock held by Spike Up Media A.B. ("Spike Up AB") and 39,172 shares of common stock issuable upon exercise of a warrant of the Issuer held by Spike Up Media LLC ("Spike Up LLC"). Spike Up LLC is a wholly owned indirect subsidiary of Spike Up A.B., which is a wholly owned subsidiary of Ellmount Interactive A. B. ("Interactive"). Cascadia and OEH Invest AB ("OEH") own 66.9% and 33.1% of Interactive, respectively. Michael Cribari and Brandon Eachus as principal shareholders of Cascadia have joint voting and dispositive authority over the shares of Issuer held directly by Cascadia.
3. OEH and Cascadia may be deemed to have joint voting and joint dispositive power over the securities of the Issuer beneficially held by Interactive and a minority shareholder of Cascadia, who has no voting or dispositive power over shares directly held by Cascadia, may be deemed to have a limited pecuniary interest in the shares held indirectly by Interactive.
/s/ Brandon Eachus, Director05/26/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

What insider change did Cascadia Holdings report in High Roller Technologies (ROLR)?

Cascadia reported an internal restructuring, distributing 787,648 High Roller Technologies shares to one of its shareholders. The transfer occurred for no additional consideration under a share redemption agreement and did not involve open-market buying or selling of ROLR shares.

How many High Roller Technologies (ROLR) shares did Cascadia distribute?

Cascadia distributed 787,648 shares of High Roller Technologies common stock to one of its shareholders. The transfer was made pro rata to that shareholder’s interest and completed under a share redemption agreement without any additional cash consideration changing hands.

What is Cascadia’s direct ownership in High Roller Technologies (ROLR) after the restructuring?

Following the restructuring, Cascadia reports direct ownership of 1,800,748 shares of High Roller Technologies common stock. This direct stake is in addition to indirect interests held through affiliated entities, as described in the detailed beneficial ownership footnotes.

What indirect interests in High Roller Technologies (ROLR) are linked to Cascadia?

Cascadia is associated with indirect joint beneficial ownership of High Roller shares held by Spike Up Media A.B. and shares issuable under a warrant held by Spike Up Media LLC. These structures sit under Ellmount Interactive A.B., in which Cascadia and OEH Invest AB hold controlling stakes.

What warrant exposure to High Roller Technologies (ROLR) is disclosed in this filing?

The filing shows an indirectly held warrant with a $2.37 per share exercise price, expiring June 30, 2027. This warrant is exercisable into High Roller common stock and represents additional potential equity exposure connected to Cascadia’s broader ownership structure.

Did Cascadia buy or sell High Roller Technologies (ROLR) shares on the open market?

No open-market purchases or sales are reported. The main change is a distribution of 787,648 shares from Cascadia to one shareholder under a share redemption agreement, which is categorized as an “other” type restructuring transaction, not a market trade.