<SEC-DOCUMENT>0001179110-21-007987.txt : 20210806
<SEC-HEADER>0001179110-21-007987.hdr.sgml : 20210806
<ACCEPTANCE-DATETIME>20210806144204
ACCESSION NUMBER:		0001179110-21-007987
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20210803
FILED AS OF DATE:		20210806
DATE AS OF CHANGE:		20210806

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			GEYGAN JEFFREY RICHART GEYGAN
		CENTRAL INDEX KEY:			0001733547

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-26408
		FILM NUMBER:		211152407

	MAIL ADDRESS:	
		STREET 1:		1433 N WATER STREET
		STREET 2:		SUITE 549
		CITY:			MILWAUKEE
		STATE:			WI
		ZIP:			53202

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Wayside Technology Group, Inc.
		CENTRAL INDEX KEY:			0000945983
		STANDARD INDUSTRIAL CLASSIFICATION:	WHOLESALE-COMPUTER & PERIPHERAL EQUIPMENT & SOFTWARE [5045]
		IRS NUMBER:				133136104
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		4 INDUSTRIAL WAY WEST
		STREET 2:		SUITE 300
		CITY:			EATONTOWN
		STATE:			NJ
		ZIP:			07724
		BUSINESS PHONE:		732-389-0932

	MAIL ADDRESS:	
		STREET 1:		4 INDUSTRIAL WAY WEST
		STREET 2:		SUITE 300
		CITY:			EATONTOWN
		STATE:			NJ
		ZIP:			07724

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	PROGRAMMERS PARADISE INC
		DATE OF NAME CHANGE:	19950531
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>edgar.xml
<DESCRIPTION>FORM 4 -
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0306</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2021-08-03</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0000945983</issuerCik>
        <issuerName>Wayside Technology Group, Inc.</issuerName>
        <issuerTradingSymbol>WSTG</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001733547</rptOwnerCik>
            <rptOwnerName>GEYGAN JEFFREY RICHART GEYGAN</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>4 INDUSTRIAL WAY WEST</rptOwnerStreet1>
            <rptOwnerStreet2>SUITE 300</rptOwnerStreet2>
            <rptOwnerCity>EATONTOWN</rptOwnerCity>
            <rptOwnerState>NJ</rptOwnerState>
            <rptOwnerZipCode>07724</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
            <officerTitle></officerTitle>
            <otherText></otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2021-08-03</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>2322</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>17852</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2021-08-03</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>J</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F3"/>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>0</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>133560</value>
                    <footnoteId id="F1"/>
                    <footnoteId id="F2"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>Held by GVIC</value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable></derivativeTable>

    <footnotes>
        <footnote id="F1">The securities are held in account(s) managed indirectly by Global Value Investment Corporation (&quot;GVIC&quot;) which is controlled by the reporting person. The securities may be deemed to be beneficially owned by the reporting person because he controls the registered investment adviser, which may be deemed to have beneficial ownership of the securities because it serves as the investment manager to separate managed accounts. The reporting person does not have any direct or indirect pecuniary interest in the managed account(s) because the reporting person (i) does not receive any incentive compensation from the managed account(s) and (ii) does not have a direct or indirect interest in the managed account(s).</footnote>
        <footnote id="F2">The reporting person disclaims beneficial ownership in the securities reported on this Form 4 except to the extent of his pecuniary interest, if any, therein, and this report shall not be deemed to be an admission that the reporting person is the beneficial owner of such securities for purposes of Section 16 of the Security Exchange Act of 1934, as amended, or for any other purpose.</footnote>
        <footnote id="F3">There are no transactions being reported on this line item of this Form 4, it is being used to report the Direct ownership of the reporting person.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Jeffrey Geygan</signatureName>
        <signatureDate>2021-08-06</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
