<SEC-DOCUMENT>0001558370-21-007798.txt : 20210527
<SEC-HEADER>0001558370-21-007798.hdr.sgml : 20210527
<ACCEPTANCE-DATETIME>20210527155926
ACCESSION NUMBER:		0001558370-21-007798
CONFORMED SUBMISSION TYPE:	DEFA14A
PUBLIC DOCUMENT COUNT:		1
FILED AS OF DATE:		20210527
DATE AS OF CHANGE:		20210527

FILER:

	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

	FILING VALUES:
		FORM TYPE:		DEFA14A
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-26408
		FILM NUMBER:		21972516

	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>DEFA14A
<SEQUENCE>1
<FILENAME>tmb-20210527xdefa14a.htm
<DESCRIPTION>DEFA14A
<TEXT>
<!--Enhanced HTML document created with Toppan Merrill Bridge  9.10.0.88--><!--Created on: 5/27/2021 07:59:17 PM (UTC)--><!DOCTYPE HTML PUBLIC "-//W3C//DTD HTML 4.01 Transitional//EN" "http://www.w3.org/TR/html4/loose.dtd"><html><head><meta charset="UTF-8"><title></title></head><body><div style="margin-top:30pt;"></div><div style="max-width:100%;padding-left:4.08%;padding-right:3.59%;position:relative;"><div style="clear:both;max-width:100%;position:relative;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11pt;text-align:center;margin:3.7pt 2.95pt 0pt 0pt;"><b style="font-weight:bold;">UNITED</b><b style="font-weight:bold;letter-spacing:-0.35pt;"> </b><b style="font-weight:bold;">STATES</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:10.9pt;text-align:center;margin:0pt 2.95pt 0pt 0pt;"><b style="font-weight:bold;">SECURITIES AND EXCHANGE</b><b style="font-weight:bold;letter-spacing:-0.9pt;"> </b><b style="font-weight:bold;">COMMISSION</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:2.32;text-align:center;margin:0pt 212.5pt 0pt 209.55pt;"><b style="font-weight:bold;">Washington, D.C.</b><b style="font-weight:bold;letter-spacing:-0.35pt;"> </b><b style="font-weight:bold;">20549 SCHEDULE</b><b style="font-weight:bold;letter-spacing:-0.3pt;"> </b><b style="font-weight:bold;">14A</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11pt;text-align:center;margin:0pt 2.95pt 0pt 0pt;">Proxy Statement Pursuant to Section 14(a)<font style="letter-spacing:-1.15pt;"> </font>of</p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11.4pt;text-align:center;margin:0pt 2.8pt 0pt 0pt;">the Securities Exchange Act of 1934<font style="letter-spacing:-0.95pt;"> </font></p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0.3pt 0pt 0pt 0pt;"><font style="font-size:6pt;visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:3.04pt 138.45pt 0pt 11pt;">Filed by the Registrant<font style="letter-spacing:2.4pt;"> </font><font style="font-family:'Segoe UI Symbol';">&#9746;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0.4pt 0pt 0pt 0pt;"><font style="font-family:'Verdana';font-size:7.5pt;visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt 138.45pt 0pt 10.95pt;">Filed<font style="letter-spacing:-0.85pt;"> </font>by<font style="letter-spacing:-0.85pt;"> </font>a<font style="letter-spacing:-0.85pt;"> </font>Party<font style="letter-spacing:-0.9pt;"> </font>other<font style="letter-spacing:-0.9pt;"> </font>than<font style="letter-spacing:-0.85pt;"> </font>the<font style="letter-spacing:-0.95pt;"> </font>Registrant<font style="letter-spacing:0.9pt;"> </font><font style="font-family:'Segoe UI Symbol';">&#9744;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0.05pt 0pt 0pt 0pt;"><font style="font-family:'Verdana';font-size:9pt;visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:10.9pt;margin:0pt 138.45pt 0pt 10.95pt;">Check the appropriate<font style="letter-spacing:-0.95pt;"> </font>box:</p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11pt;margin:0pt 0pt 0pt 11pt;"><font style="display:inline-block;text-indent:0pt;width:27.05pt;"><font style="color:#000000;font-family:'Segoe UI Symbol';font-size:10pt;font-style:normal;font-weight:normal;line-height:11pt;text-align:left;">&#9744;</font></font><font style="vertical-align:super;">Preliminary Proxy</font><font style="letter-spacing:-0.85pt;vertical-align:super;"> </font><font style="vertical-align:super;">Statement</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11pt;margin:0pt 0pt 0pt 11pt;"><font style="display:inline-block;text-indent:0pt;width:26.95pt;"><font style="color:#000000;font-family:'Segoe UI Symbol';font-size:10pt;font-style:normal;font-weight:normal;line-height:11pt;text-align:left;">&#9744;</font></font><b style="font-weight:bold;">Confidential,</b><b style="font-weight:bold;letter-spacing:-0.15pt;"> </b><b style="font-weight:bold;">for</b><b style="font-weight:bold;letter-spacing:-0.25pt;"> </b><b style="font-weight:bold;">Use</b><b style="font-weight:bold;letter-spacing:-0.2pt;"> </b><b style="font-weight:bold;">of</b><b style="font-weight:bold;letter-spacing:-0.2pt;"> </b><b style="font-weight:bold;">the</b><b style="font-weight:bold;letter-spacing:-0.25pt;"> </b><b style="font-weight:bold;">Commission</b><b style="font-weight:bold;letter-spacing:-0.2pt;"> </b><b style="font-weight:bold;">Only</b><b style="font-weight:bold;letter-spacing:-0.25pt;"> </b><b style="font-weight:bold;">(as</b><b style="font-weight:bold;letter-spacing:-0.2pt;"> </b><b style="font-weight:bold;">permitted</b><b style="font-weight:bold;letter-spacing:-0.2pt;"> </b><b style="font-weight:bold;">by</b><b style="font-weight:bold;letter-spacing:-0.25pt;"> </b><b style="font-weight:bold;">Rule</b><b style="font-weight:bold;letter-spacing:-0.25pt;"> </b><b style="font-weight:bold;">14a-6(e)(2))</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:10.9pt;margin:0pt 0pt 0pt 10.95pt;"><font style="display:inline-block;text-indent:0pt;width:27pt;"><font style="color:#000000;font-family:'Segoe UI Symbol';font-size:10pt;font-style:normal;font-weight:normal;line-height:10.9pt;text-align:left;">&#9744;</font></font>Definitive Proxy<font style="letter-spacing:-0.75pt;"> </font>Statement</p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11.25pt;margin:0pt 0pt 0pt 10.95pt;"><font style="display:inline-block;text-indent:0pt;width:27.1pt;"><font style="color:#000000;font-family:'Segoe UI Symbol';font-size:10pt;font-style:normal;font-weight:normal;line-height:11.25pt;text-align:left;">&#9746;</font></font>Definitive Additional<font style="letter-spacing:-0.9pt;"> </font>Materials</p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:11pt;margin:0pt 0pt 0pt 11pt;"><font style="display:inline-block;text-indent:0pt;width:27.05pt;"><font style="color:#000000;font-family:'Segoe UI Symbol';font-size:10pt;font-style:normal;font-weight:normal;line-height:11pt;text-align:left;">&#9744;</font></font>Soliciting Material under<font style="letter-spacing:-1.05pt;"> </font>&#167; 240.14a-12</p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0.5pt 0pt 0pt 0pt;"><font style="font-size:8.5pt;visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:center;margin:0pt 3pt 0pt 0pt;">WAYSIDE TECHNOLOGY GROUP,<font style="letter-spacing:-0.8pt;"> </font>INC.</p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1pt;margin:0pt 0pt 0pt 10.6pt;"><font style="font-size:1pt;line-height:1.19;margin-left:0pt;visibility:hidden;">&#8203;</font></p><div style="font-family:'Times New Roman','Times','serif';font-size:10.0pt;margin-bottom:0pt;margin-right:2.9pt;min-height:1.19em;position:relative;width:100%;"><hr noshade="true" color="#000000" size="1" width="95.0%" style="background-color:#000000;color:#000000;height:1pt;position:relative;top:0.6em;border:none;margin:0 auto;" align="center"></div><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:center;margin:0pt 2.9pt 0pt 0pt;">(Name of Registrant as Specified in its<font style="letter-spacing:-1.6pt;"> </font>Charter)</p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0.34pt 0pt 0pt 0pt;"><font style="visibility:hidden;">&#8203;</font></p><div style="font-family:'Times New Roman','Times','serif';font-size:12.0pt;margin-bottom:0pt;min-height:1.19em;position:relative;width:100%;"><hr noshade="true" color="#000000" size="1" width="95.0%" style="background-color:#000000;color:#000000;height:1pt;position:relative;top:0.6em;border:none;margin:0 auto;" align="center"></div><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:center;margin:0pt;">(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)</p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;min-height:21.5pt;text-align:justify;margin:0pt 138.45pt 0pt 0pt;">Payment of Filing Fee (Check the appropriate<font style="letter-spacing:-1.35pt;"> </font>box):</p><div align="left"><table style="border-collapse:collapse;font-size:16pt;height:max-content;padding-left:0pt;padding-right:0pt;width:100%;"><tr style="height:1pt;"><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><div style="height:1pt;overflow:hidden;overflow-wrap:break-word;position:relative;"><div style="bottom:0pt;position:absolute;width:100%;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:1pt;visibility:hidden;">&#8203;</font></p></div></div></td><td colspan="2" style="vertical-align:bottom;width:95.22%;margin:0pt;padding:0pt;"><div style="height:1pt;overflow:hidden;overflow-wrap:break-word;position:relative;"><div style="bottom:0pt;position:absolute;width:100%;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:1pt;visibility:hidden;">&#8203;</font></p></div></div></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-family:'Segoe UI Symbol';">&#9746;</font></p></td><td colspan="2" style="vertical-align:bottom;width:95.22%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">No fee<font style="letter-spacing:-0.55pt;"> </font>required.</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-family:'Segoe UI Symbol';">&#9744;</font></p></td><td colspan="2" style="vertical-align:bottom;width:95.22%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and<font style="letter-spacing:-1.65pt;"> </font>0-11.</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(1)</p></td><td style="vertical-align:bottom;width:91.93%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Title<font style="letter-spacing:-0.25pt;"> </font>of<font style="letter-spacing:-0.3pt;"> </font>each<font style="letter-spacing:-0.35pt;"> </font>class<font style="letter-spacing:-0.25pt;"> </font>of<font style="letter-spacing:-0.3pt;"> </font>securities<font style="letter-spacing:-0.3pt;"> </font>to<font style="letter-spacing:-0.25pt;"> </font>which<font style="letter-spacing:-0.25pt;"> </font>transaction<font style="letter-spacing:-0.3pt;"> </font>applies:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(2)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Aggregate<font style="letter-spacing:-0.3pt;"> </font>number<font style="letter-spacing:-0.3pt;"> </font>of<font style="letter-spacing:-0.3pt;"> </font>securities<font style="letter-spacing:-0.35pt;"> </font>to<font style="letter-spacing:-0.3pt;"> </font>which<font style="letter-spacing:-0.3pt;"> </font>transaction<font style="letter-spacing:-0.3pt;"> </font>applies:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:top;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(3)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount<font style="letter-spacing:-0.15pt;"> </font>on<font style="letter-spacing:-0.15pt;"> </font>which<font style="letter-spacing:-0.2pt;"> </font>the<font style="letter-spacing:-0.15pt;"> </font>filing<font style="letter-spacing:-0.15pt;"> </font>fee<font style="letter-spacing:-0.15pt;"> </font>is<font style="letter-spacing:-0.2pt;"> </font>calculated<font style="letter-spacing:-0.15pt;"> </font>and<font style="letter-spacing:-0.2pt;"> </font>state<font style="letter-spacing:-0.15pt;"> </font>how<font style="letter-spacing:-0.2pt;"> </font>it<font style="letter-spacing:-0.15pt;"> </font>was<font style="letter-spacing:-0.15pt;"> </font>determined):</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(4)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Proposed maximum aggregate value of<font style="letter-spacing:-1.3pt;"> </font>transaction:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(5)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Total fee<font style="letter-spacing:-0.4pt;"> </font>paid:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-family:'Segoe UI Symbol';">&#9744;</font></p></td><td colspan="2" style="vertical-align:bottom;width:95.22%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Fee paid previously with preliminary<font style="letter-spacing:-1.55pt;"> </font>materials.</p></td></tr><tr><td style="vertical-align:top;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-family:'Segoe UI Symbol';">&#9744;</font></p></td><td colspan="2" style="vertical-align:bottom;width:95.22%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Check box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its<font style="letter-spacing:-0.5pt;"> </font>filing.</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(1)</p></td><td style="vertical-align:bottom;width:91.93%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Amount Previously<font style="letter-spacing:-0.7pt;"> </font>Paid:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(2)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Form, Schedule or Registration Statement<font style="letter-spacing:-1.1pt;"> </font>No.:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 11pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(3)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Filing<font style="letter-spacing:-0.45pt;"> </font>Party:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 65pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 65pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">(4)</p></td><td style="vertical-align:bottom;width:91.93%;border-top:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;margin:0pt;">Date<font style="letter-spacing:-0.35pt;"> </font>Filed:</p></td></tr><tr><td style="vertical-align:bottom;width:4.77%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt 0pt 0pt 65pt;"><font style="font-size:10pt;margin-left:0pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:3.28%;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td><td style="vertical-align:bottom;width:91.93%;border-bottom:1px solid #000000;margin:0pt;padding:0pt;"><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="font-size:10pt;visibility:hidden;">&#8203;</font></p></td></tr></table></div><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;margin:0pt;"><font style="visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:2.25pt;margin:0pt 0pt 0pt 9.85pt;"><font style="font-size:2.25pt;line-height:1.19;margin-left:0pt;visibility:hidden;">&#8203;</font></p><p style="display:none;font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:0pt;margin:0pt;"><font style="font-size:0pt;line-height:1.19;visibility:hidden;">&#8203;</font></p></div></div><hr style="background-color:#000000;clear:both;color:#000000;height:2pt;line-height:0;margin-bottom:30pt;margin-left:4.08%;margin-right:3.59%;margin-top:30pt;page-break-after:always;width:92.32%;border-width:0;"><div style="max-width:100%;padding-left:11.76%;padding-right:11.76%;position:relative;"><div style="margin-top:14.4pt;width:100%;"><p style="font-family:'Calibri','Helvetica','sans-serif';font-size:11pt;line-height:1.19;margin:0pt;"><font style="visibility:hidden;">&#8203;</font></p></div><div style="clear:both;max-width:100%;position:relative;"><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:center;margin:0pt;"><b style="font-weight:bold;">SUPPLEMENT TO PROXY STATEMENT</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:center;margin:0pt;"><b style="font-weight:bold;">FOR THE 2021 ANNUAL MEETING OF STOCKHOLDERS</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:center;margin:0pt;"><b style="font-weight:bold;">To Be Held on Tuesday, June 8, 2021</b></p><p style="font-family:'Times New Roman','Times','serif';font-size:12pt;line-height:1.19;text-align:center;margin:0pt;"><font style="font-size:10pt;font-weight:bold;visibility:hidden;">&#8203;</font></p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:justify;margin:0pt;">On April 16, 2021, Wayside Technology Group, Inc. (the &#8220;Company&#8221;), filed its definitive Proxy Statement (&#8220;Proxy Statement&#8221;) and form of Proxy relating to the solicitation of proxies by the Company in connection with its 2021 Annual Meeting of Stockholders to be held on June 8, 2021 (the &#8220;2021 Annual Meeting&#8221;) with the Securities and Exchange Commission (the &#8220;SEC&#8221;). The Proxy Statement is available on the Internet at www.waysidetechnology.com/investors/sec-filings and also is available on the website maintained by the SEC at www.sec.gov. This Supplement, dated May 27, 2021 (this &#8220;Supplement&#8221;), supplements the Proxy Statement and should be read in conjunction with the Proxy Statement, which should be read in its entirety.</p><p style="font-family:'Times New Roman','Times','serif';font-size:10pt;line-height:1.19;text-align:justify;margin:12pt 0pt 12pt 0pt;">This Supplement relates to <b style="font-weight:bold;">Proposal 4: Wayside Technology Group, Inc. 2021 Omnibus Incentive Plan </b>(the &#8220;2021 Plan&#8221;)<b style="font-weight:bold;">. </b>If approved by the Company&#8217;s stockholders, the 2021 Plan will replace the Wayside Technology Group, Inc. 2012 Stock-Based Compensation Plan (as amended, the &#8220;2012 Plan&#8221;). This Supplement is being made to clarify that no shares have been granted as awards under the 2012 Plan since March 31, 2021 and that the Company has made a commitment to not grant any additional shares under the 2012 Plan unless the 2021 Plan is not approved by the Company&#8217;s stockholders. As of March 31, 2021 and as of the date hereof, there were 331,974 shares of Common Stock available for grant under the 2012 Plan. None of these remaining shares of Common Stock authorized under the 2012 Plan will be transferred to or used under the 2021 Plan nor will any awards under the 2012 Plan that are forfeited increase the shares available for awards under the 2021 Plan. As of March 31, 2021, there were 158,164 unvested shares of Restricted Stock from the 2012 Plan outstanding. If 2021 Plan becomes effective, all outstanding awards under the 2012 Plan will remain outstanding.</p></div></div><hr style="background-color:#000000;clear:both;color:#000000;height:2pt;line-height:0;margin-left:11.76%;margin-right:11.76%;margin-top:30pt;page-break-after:avoid;width:76.47%;border-width:0;"></body></html>
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