Major ROLR holders revise stakes in High Roller Technologies Schedule 13D/A

Rhea-AI Filing Summary

High Roller Technologies’ major shareholders have updated their ownership positions in Amendment No. 2 to a Schedule 13D. As of April 28, 2026, Cascadia Holdings Ltd distributed 787,648 shares of High Roller common stock to Jeff Smith for no additional consideration under a share redemption agreement. After this change, Cascadia reports beneficial ownership of 2,644,423 shares, representing 24% of the common stock. Director Brandon Eachus reports beneficial ownership of 2,749,391 shares, or 24.9%, through a mix of directly held shares, vested options, and indirect interests via Cascadia and its Spike Up Media subsidiaries. Director Michael Cribari reports beneficial ownership of 2,705,475 shares, or 24.5%, on a similar basis. The reporting persons state they have not engaged in other transactions in the issuer’s stock during the past 60 days.

Insights

Equity ownership and governance analyst

Large holders update their stakes without new buying or selling activity.

The filing shows a structural change in how a big block of High Roller Technologies shares is held, rather than fresh market purchases or sales. Cascadia distributed 787,648 shares to Jeff Smith, reducing his shared voting and dispositive power over Cascadia’s remaining stake.

Post-transaction, Cascadia reports 24% beneficial ownership, while insiders Brandon Eachus and Michael Cribari each report just under 25% when their direct and indirect holdings are combined. Control remains concentrated among a small group of related holders, which can influence governance outcomes such as board elections.

The reporting persons state they have not traded Common Stock in the last 60 days, and derivative securities not exercisable within 60 days are excluded. Future ownership disclosures in subsequent periods will clarify whether this redistribution leads to any further changes in voting influence.

Key Figures

Cascadia beneficial ownership: 2,644,423 shares (24%) Eachus beneficial ownership: 2,749,391 shares (24.9%) Cribari beneficial ownership: 2,705,475 shares (24.5%) +5 more

8 metrics

Cascadia beneficial ownership 2,644,423 shares (24%) High Roller common stock beneficially owned by Cascadia Holdings Ltd, based on 11,008,699 shares outstanding

Eachus beneficial ownership 2,749,391 shares (24.9%) High Roller common stock beneficially owned by Brandon Eachus, based on 11,023,699 shares outstanding

Cribari beneficial ownership 2,705,475 shares (24.5%) High Roller common stock beneficially owned by Michael Cribari, based on 11,023,699 shares outstanding

Cascadia distribution 787,648 shares High Roller common shares distributed by Cascadia to Jeff Smith on April 28, 2026

Cascadia direct holdings 1,800,748 shares High Roller common stock held directly by Cascadia Holdings Ltd

Spike Up Media holdings 804,503 shares + 39,172 warrants High Roller common stock and warrants beneficially held by Spike Up Media subsidiaries of Cascadia

Shares outstanding baseline 1 11,008,699 shares High Roller common stock outstanding used to calculate Cascadia’s 24% stake

Shares outstanding baseline 2 11,023,699 shares High Roller common stock outstanding used to calculate Eachus and Cribari percentages

Key Terms

beneficial ownership, shared voting power, shared dispositive power, pecuniary interest, +1 more

5 terms

beneficial ownership financial

"Beneficial ownership is based on 11,008,699 shares of common stock outstanding."

Beneficial ownership means the person or entity that actually enjoys the benefits of owning shares or other assets — such as receiving dividends, voting rights, or price gains — even if the legal title is held in another name. For investors it matters because knowing who truly controls and profits from a company reveals who can influence decisions, exposes potential conflicts of interest or hidden concentration of power, and affects transparency and risk in the stock.

shared voting power financial

"Shared Voting Power 2,644,423.00"

Shared voting power occurs when two or more parties jointly have the right to vote or decide how a block of company shares is cast, like co-owners who must agree before moving a piece of furniture. Investors care because who controls voting rights affects board elections, major corporate decisions and takeover outcomes, and shared control can alter regulatory disclosures and the practical influence any holder has over a company’s direction and value.

shared dispositive power financial

"Shared Dispositive Power 2,644,423.00"

pecuniary interest financial

"Mr. Smith may be deemed to have a limited pecuniary interest in the Issuer shares held indirectly by Ellmount."

Schedule 13D regulatory

"This Amendment No. 2 amends and supplements the filed with the U.S. Securities and Exchange Commission"

A Schedule 13D is a legal document that investors file with regulators when they buy a large enough stake in a company to potentially influence its management or decisions. It provides details about the investor’s intention, ownership stake, and plans, helping other investors understand who is gaining control and what their motives might be.

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SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 13D

Under the Securities Exchange Act of 1934

(Amendment No. 2)

High Roller Technologies, Inc.

(Name of Issuer)

Common Stock, $0.001 par value per share

(Title of Class of Securities)

42981K100

(CUSIP Number)

Brandon Eachus
c/o High Roller Technologies, Inc., 400 South 4th Street, Suite 500-#390
Las Vegas, NV, 89101
(702) 509-5244

(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)

04/28/2026

(Date of Event Which Requires Filing of This Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.

The information required on the remainder of this cover page shall not be deemed to be "filed" for the purpose of Section 18 of the Securities Exchange Act of 1934 ("Act") or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

schemaVersion:

SCHEDULE 13D

CUSIP Number(s): 42981K100

1

Name of reporting person

Cascadia Holdings Ltd

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

PF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

MALTA

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 2,644,423.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 2,644,423.00

11

Aggregate amount beneficially owned by each reporting person

2,644,423.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

24 %

14

Type of Reporting Person (See Instructions)

OO

Comment for Type of Reporting Person:

Securities disclosed herein consist of (i) 1,800,748 shares of the Issuer's common stock, par value $0.001 per share, held directly by Cascadia Holdings Limited ("Cascadia") and (ii) 804,503 shares of common stock and warrants to purchase 39,172 shares of common stock, beneficially held by Spike Up Media A.B. and Spike Up Media LLC, indirect wholly owned subsidiaries of Cascadia. Beneficial ownership is based on 11,008,699 shares of common stock outstanding.

SCHEDULE 13D

CUSIP Number(s): 42981K100

1

Name of reporting person

Brandon Eachus

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

PF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 104,968.00
8	Shared Voting Power 2,644,423.00
9	Sole Dispositive Power 104,968.00
10	Shared Dispositive Power 2,644,423.00

11

Aggregate amount beneficially owned by each reporting person

2,749,391.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

24.9 %

14

Type of Reporting Person (See Instructions)

IN

Comment for Type of Reporting Person:

Securities disclosed herein consist of (i) 89,968 shares of common stock and fully vested options to purchase additional 15,000 shares of common stock of the Issuer held directly by Mr. Eachus, (ii) 1,800,748 shares of common stock held directly by Cascadia Holdings Limited ("Cascadia") and (iii) 804,503 shares of common stock and warrants to purchase 39,172 shares of common stock, beneficially held by Spike Up Media A.B. and Spike Up Media LLC, which are indirect wholly owned subsidiaries of Cascadia. Beneficial ownership is based on 11,023,699 shares of common stock outstanding. Excludes derivative securities not exercisable within 60 days from the date of the filing of this Amendment No.2 to Schedule 13D.

SCHEDULE 13D

CUSIP Number(s): 42981K100

1

Name of reporting person

Michael Cribari

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

PF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 61,052.00
8	Shared Voting Power 2,644,423.00
9	Sole Dispositive Power 61,052.00
10	Shared Dispositive Power 2,644,423.00

11

Aggregate amount beneficially owned by each reporting person

2,705,475.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

24.5 %

14

Type of Reporting Person (See Instructions)

IN

Comment for Type of Reporting Person:

Securities disclosed herein consist of (i) 46,052 shares of common stock and fully vested options to purchase additional 15,000 shares of common stock of the Issuer held directly by Mr. Cribari, (ii) 1,800,748 shares of common stock held directly by Cascadia Holdings Limited ("Cascadia") and (iii) 804,503 shares of common stock and warrants to purchase 39,172 shares of common stock, beneficially held by Spike Up Media A.B. and Spike Up Media LLC, indirect wholly owned subsidiaries of Cascadia. Beneficial ownership is based on 11,023,699 shares of common stock outstanding. Excludes derivative securities not exercisable within 60 days from the date of the filing of this Amendment No.2 to Schedule 13D.

SCHEDULE 13D

Item 1.	Security and Issuer
(a)	Title of Class of Securities: Common Stock, $0.001 par value per share
(b)	Name of Issuer: High Roller Technologies, Inc.
(c)	Address of Issuer's Principal Executive Offices: 400 South 4th Street, Suite 500-#390, Las Vegas, NEVADA , 89101.
Item 1 Comment: This Amendment No. 2 amends and supplements the Schedule 13D filed with the U.S. Securities and Exchange Commission (the "SEC") on November 5, 2024, as amended by Amendment No. 2 filed with the SEC on November 5, 2024, relating to the common stock of High Roller Technologies, Inc., a Delaware corporation (the "Issuer"). Except as set forth herein, the Schedule 13D is unmodified and remains in full force and effect. Each capitalized term used but not defined herein has the meaning ascribed to such term in the Schedule 13D.
Item 5.	Interest in Securities of the Issuer
(a)	1. As of April 28, 2026, pursuant to share redemption agreement between Cascadia and Jeff Smith, Cascadia distributed 787,648 shares of common stock of the Issuer to Mr. Smith pro rata to his interest in Cascadia for no additional consideration (the "Distribution"). 2. Following the Distribution, Mr. Smith ceased to be a beneficial owner of the shares of common stock of the Issuer held by Cascadia and no longer has shared voting or shared dispositive power over shares of common stock of the Issuer held by Cascadia. Mr. Smith may be deemed to have a limited pecuniary interest in the Issuer shares held indirectly by Ellmount.
(b)	The information contained on the cover pages to this Amendment is incorporated by reference herein.
(c)	The Reporting Persons have not engaged in any transaction during the past 60 days involving the Common Stock of the Issuer.
(d)	Not applicable.
(e)	Not applicable.
Item 7.	Material to be Filed as Exhibits.
	None

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

Cascadia Holdings Ltd

Signature:	/s/ Brandon Eachus
Name/Title:	Brandon Eachus, Director
Date:	05/29/2026

Brandon Eachus

Signature:	/s/ Brandon Eachus
Name/Title:	Brandon Eachus
Date:	05/29/2026

Michael Cribari

Signature:	/s/ Michael Cribari
Name/Title:	Michael Cribari
Date:	05/29/2026

FAQ

What does High Roller Technologies’ Schedule 13D/A Amendment No. 2 report for ROLR?

It reports updated large-shareholder positions in High Roller Technologies. Cascadia, Brandon Eachus, and Michael Cribari disclose their current beneficial ownership percentages and share counts following an internal share distribution, with no other recent trading activity reported.

How many High Roller Technologies shares does Cascadia Holdings Ltd beneficially own?

Cascadia Holdings Ltd reports beneficial ownership of 2,644,423 shares of High Roller Technologies common stock. This represents 24% of the outstanding common stock, based on 11,008,699 shares outstanding as referenced in the Schedule 13D/A amendment.

What is Brandon Eachus’s beneficial ownership in High Roller Technologies (ROLR)?

Brandon Eachus reports beneficial ownership of 2,749,391 shares of High Roller common stock. This equals 24.9% of the class, combining his directly held shares, vested options, and indirect interests through Cascadia and its Spike Up Media subsidiaries.

What is Michael Cribari’s beneficial ownership stake in High Roller Technologies?

Michael Cribari reports beneficial ownership of 2,705,475 shares of High Roller common stock. This represents 24.5% of the class, including his direct holdings, vested options, and indirect interests through Cascadia and its Spike Up Media subsidiaries.

What transaction triggered this High Roller Technologies Schedule 13D/A amendment?

The amendment reflects a share distribution on April 28, 2026. Cascadia distributed 787,648 High Roller common shares to Jeff Smith for no additional consideration, adjusting beneficial ownership and shared voting power among the remaining reporting persons.

Have the reporting persons traded High Roller Technologies stock recently?

The reporting persons state they have not engaged in any transactions involving High Roller common stock during the past 60 days. The disclosed positions therefore primarily reflect the internal share distribution rather than market purchases or sales.