<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4/A</documentType>

    <periodOfReport>2023-11-17</periodOfReport>

    <dateOfOriginalSubmission>2023-11-20</dateOfOriginalSubmission>

    <issuer>
        <issuerCik>0000776867</issuerCik>
        <issuerName>WHITE MOUNTAINS INSURANCE GROUP LTD</issuerName>
        <issuerTradingSymbol>WTM</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001186549</rptOwnerCik>
            <rptOwnerName>Hicks Weston M</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O WHITE MOUNTAINS INSURANCE GROUP, LTD</rptOwnerStreet1>
            <rptOwnerStreet2>23 SOUTH MAIN STREET, SUITE 3B</rptOwnerStreet2>
            <rptOwnerCity>HANOVER</rptOwnerCity>
            <rptOwnerState>NH</rptOwnerState>
            <rptOwnerZipCode>03755</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Shares</value>
            </securityTitle>
            <transactionDate>
                <value>2023-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>52</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1476.15</value>
                    <footnoteId id="F1"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>1358</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Shares</value>
            </securityTitle>
            <transactionDate>
                <value>2023-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>120</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1476.74</value>
                    <footnoteId id="F2"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>1478</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Shares</value>
            </securityTitle>
            <transactionDate>
                <value>2023-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>579</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1479.88</value>
                    <footnoteId id="F3"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>2057</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Shares</value>
            </securityTitle>
            <transactionDate>
                <value>2023-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>11</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1483.43</value>
                    <footnoteId id="F4"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>2068</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Shares</value>
            </securityTitle>
            <transactionDate>
                <value>2023-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>238</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1484.96</value>
                    <footnoteId id="F5"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>2306</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <footnotes>
        <footnote id="F1">The price reported in Column 4 is a weighted average price.  These shares were purchased in multiple transactions at prices ranging from $1475.51 to $1476.32, inclusive.  The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares transacted at each separate price within the ranges set forth in footnotes (1) to (5) of this Form 4.</footnote>
        <footnote id="F2">The price reported in Column 4 is a weighted average price.  These shares were purchased in multiple transactions at prices ranging from $1476.55 to $1476.92, inclusive.</footnote>
        <footnote id="F3">The price reported in Column 4 is a weighted average price.  These shares were purchased in multiple transactions at prices ranging from $1479.35 to $1480.01, inclusive.</footnote>
        <footnote id="F4">The price reported in Column 4 is a weighted average price.  These shares were purchased in multiple transactions at prices ranging from $1483.13 to $1483.78, inclusive.</footnote>
        <footnote id="F5">The price reported in Column 4 is a weighted average price.  These shares were purchased in multiple transactions at prices ranging from $1484.28 to $1485.00, inclusive.</footnote>
    </footnotes>

    <remarks>The footnotes in this report are amended to make clear that all transactions referred to in Table I were purchases.</remarks>

    <ownerSignature>
        <signatureName>Wesley C. Bell, by Power of Attorney</signatureName>
        <signatureDate>2023-11-20</signatureDate>
    </ownerSignature>
</ownershipDocument>
