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  <!--Created: Thu May 14 19:51:13 UTC 2026-->
  <schemaVersion>X0202</schemaVersion>
  <headerData>
    <submissionType>13F-HR</submissionType>
    <filerInfo>
      <liveTestFlag>LIVE</liveTestFlag>
      <filer>
        <credentials>
          <cik>0002044285</cik>
          <ccc>XXXXXXXX</ccc>
        </credentials>
      </filer>
      <periodOfReport>03-31-2026</periodOfReport>
    </filerInfo>
  </headerData>
  <formData>
    <coverPage>
      <reportCalendarOrQuarter>03-31-2026</reportCalendarOrQuarter>
      <filingManager>
        <name>Dauntless Investment Group, LLC</name>
        <address>
          <common:street1>3283 Foxfire Dr.</common:street1>
          <common:city>Milford</common:city>
          <common:stateOrCountry>MI</common:stateOrCountry>
          <common:zipCode>48380</common:zipCode>
        </address>
      </filingManager>
      <reportType>13F HOLDINGS REPORT</reportType>
      <form13FFileNumber>028-25194</form13FFileNumber>
      <provideInfoForInstruction5>Y</provideInfoForInstruction5>
      <additionalInformation>The information included on the Information Table with respect to the holdings of AEON Biopharma, Inc. ("AEON") and Femasys Inc. ("FEMY") reflect the exercise of Pre-funded Warrants and/or Common Warrants held by Dauntless Investment Group, LLC ("DIG") after giving effect to provisions that prevent the exercise of such securities if the beneficial ownership of such entity would exceed 9.99% of the underlying security following such exercise. The information included on the Information Table with respect to the holdings of Quoin Pharmaceuticals Ltd. ("QNRX") and Tiziana Life Sciences Ltd. ("TLSA") reflect the exercise of Common Warrants held by DIG. As of March 31, 2026, DIG held an aggregate of 2,527,775 Common Shares of AEON, 6,033,030 Common Shares of FEMY, 196,592 Common Shares of QNRX and 2,165,231 Common Shares of TLSA.</additionalInformation>
    </coverPage>
    <signatureBlock>
      <name>Matthew Okkerse</name>
      <title>CFO</title>
      <phone>734.770.0040</phone>
      <signature>/s/ Matthew Okkerse</signature>
      <city>Milford</city>
      <stateOrCountry>MI</stateOrCountry>
      <signatureDate>05-14-2026</signatureDate>
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      <otherIncludedManagersCount>0</otherIncludedManagersCount>
      <tableEntryTotal>69</tableEntryTotal>
      <tableValueTotal>151045892</tableValueTotal>
      <isConfidentialOmitted>true</isConfidentialOmitted>
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