<SEC-DOCUMENT>0001179110-19-009300.txt : 20190808
<SEC-HEADER>0001179110-19-009300.hdr.sgml : 20190808
<ACCEPTANCE-DATETIME>20190808153537
ACCESSION NUMBER:		0001179110-19-009300
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20190806
FILED AS OF DATE:		20190808
DATE AS OF CHANGE:		20190808

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:		191009270

	MAIL ADDRESS:	
		STREET 1:		1500 W MARKET STREET
		STREET 2:		SUITE 250
		CITY:			MEQUON
		STATE:			WI
		ZIP:			53092

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>2019-08-06</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>2019-08-06</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>J</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F1"/>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>7045</value>
                    <footnoteId id="F3"/>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>133168</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                    <footnoteId id="F2"/>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>Held By GVIC</value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2019-08-06</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F4"/>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>2500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>11925</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </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 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 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 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 Securities Exchange Act of 1934, as amended, or for any other purpose.</footnote>
        <footnote id="F3">As of August 6, 2019, certain separately managed accounts terminated their relationship with, and are no longer advised by, GVIC. The positions held in such accounts are therefore no longer included herein.</footnote>
        <footnote id="F4">Restricted stock granted pursuant to the Issuer's 2012 Stock-Based Compensation Plan.   These shares will vest in full on August 6, 2019.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Jeffrey Geygan</signatureName>
        <signatureDate>2019-08-08</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
