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OBOOK Holdings Inc. 4,729,695 ClassA Common Shares This prospectus supplement updates and amends the prospectus dated September29, 2025, which relates to registration of the resale of up to4,729,695 ClassA Common Shares of OBOOK Holdings Inc., by our shareholders identified in this prospectus, referred to as the registeredshareholders. Unlike an initial public offering, the resale by the registered shareholders is not being underwritten by any investment bank. The registeredshareholders may, or may not, elect to sell their ClassA Common Shares covered by this prospectus, as and to the extent they may determine. Suchsales, if any, will be made through brokerage transactions on the Nasdaq Global Market of the Nasdaq Stock Market LLC, or Nasdaq, at prevailingmarket prices. See the section titled “Plan of Distribution.” If the registered shareholders choose to sell their ClassA Common Shares, we will notreceive any proceeds from the sale of ClassA Common Shares by the registered shareholders. This prospectus supplement is being filed to update, amend and supplement the information previously included in the prospectus with theinformation attached to this prospectus supplement and incorporates by reference the information contained in the Form 6-K filed with the Securitiesand Exchange Commission on December 29, 2025. You should read this prospectus supplement together with the prospectus, which is to be deliveredwith this prospectus supplement. Our ClassA common stock is traded on the Nasdaq under the symbol “OWLS.” On December29, 2025, the last reported sale price of our ClassAcommon stock on the Nasdaq was $6.58 per share. The Securities and Exchange Commission and state securities regulators have not approved or disapproved of these securities, ordetermined if the prospectus or this prospectus supplement is truthful or complete. Any representation to the contrary is a criminal offense. The date of this prospectus supplement is December29, 2025. CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS This prospectus supplement contains forward-looking statements regarding, among other things, our business strategies, financial condition, operatingresults, and future plans. These statements are based on the current expectations, estimates, and assumptions of our management and are not guaranteesof future performance. Forward-looking statements are inherently subject to risks, uncertainties, and other factors, many of which are beyond ourcontrol. As a result, actual outcomes and results may differ materially from those expressed or implied in these statements. Forward-looking statements generally relate to future events or our future financial or operating performance and may be identified by terminology suchas “believe,” “expect,” “intend,” “anticipate,” “estimate,” “plan,” “may,” “will,” “should,” “forecast,” or similar expressions. Forward-lookingstatements in this prospectus supplement include, but are not limited to, statements regarding: •our future business performance, including revenue, operating expenses and profitability;•developments, trends and competitive conditions in the industries and markets in which we operate;•our business strategies, growth plans and product development initiatives;•our relationships with third-party partners, vendors and service providers;•government regulations and policies affecting our business;•our ability to protect our systems and infrastructure from cybersecurity threats;•our capital resources, liquidity position and potential future financing activities;•our dividend policy;•our market position and growth prospects;•general economic and market conditions; and•our ability to maintain the listing of our securities on Nasdaq. These forward-looking statements reflect our views only as of the date of this prospectus supplement. They are not intended to serve as, and must not berelied upon as, predictions of future events. Important risks and uncertainties that could cause actual results to differ materially from those anticipatedare discussed under “Risk Factors,” “Management’s Discussion and Analysis of Financial Condition and Results of Operations,” and other sections ofthe accompanying prospectus and the documents incorporated by reference therein. We qualify all of our forward-looking statements by these cautionary statements. You should not place undue reliance on forward-looking statements,and we do not undertake any obligation to update such statements to reflect events or circumstances after the date of this prospectus supplement, exceptas required by applicable law. Any updates or revisions that we may make should not be taken as an indication that further updates will be made. For additional information, you should carefully review the documents that we file with the SEC, which are available atwww.sec.gov OBOOK Holdings Inc. Announces Unaudited Financial Results for the First Half of 2025Ended June30, 2025; Core Infrastructure Transition Near Co