Exhibit 10.1

EXECUTION COPY

SETTLEMENT AGREEMENT

This Settlement Agreement (this “Agreement”), effective as of April 16, 2020
(the “Effective Date”), is entered into by and among Wayside Technology Group,
Inc., a Delaware corporation (the “Company” or “Wayside”), Simon F. Nijnens
(“Nynens”), Dennis Crowley and the persons and entities identified under that
certain SKK Schedule 13D (as defined below) as Reporting Persons (as defined
therein) (each, an “SKK Party” and collectively, the “SKK Parties”). Wayside,
Nynens and the SKK Parties are collectively referred to herein as the “Parties,”
and each of Wayside, Nynens and the collective SKK Parties, a “Party.” Unless
otherwise defined herein, capitalized terms shall have the meanings given to
them in Section 20 herein.

WHEREAS, Nynens, the former Chief Executive Officer of the Company, voluntarily
resigned from Wayside and entered into a Separation and Release Agreement with
the Company on or about May 11, 2018 (the “Separation Agreement”);

WHEREAS, pursuant to the Separation Agreement, Nynens received the full value of
Separation Benefits, defined in the Separation Agreement, from the Company,
which included an equity component (the “Equity Benefits”) amounting to 109,084
shares, of which 53,567 were withheld to satisfy tax obligations, of Wayside’s
common stock, par value $0.01 per share (the “Common Stock”) as well as a cash
component;

WHEREAS, in consideration of the Separation Benefits Nynens received from the
Company pursuant to the Separation Agreement, Nynens agreed to certain
restrictive covenants, including but not limited to a covenant not to seek
future employment with the Company and covenants not to disclose, share, or use
the Company’s confidential information;

WHEREAS, on or about November 27, 2019, Nynens entered into an agreement (the
“Group Agreement”) with Shepherd Kaplan Krochuk, LLC (“SKK”) and North & Webster
SSG, LLC (“N&W”), pursuant to which the parties agreed to form an investment
vehicle, to be advised and controlled by SKK, in order to acquire up to 100% of
the outstanding capital stock of the Company;

WHEREAS, the Group Agreement provides, among other things, that the parties to
that agreement shall use reasonable efforts to appoint Nynens as Executive
Chairman of the Company, with an annual base salary of $250,000 for a minimum
term of three (3) years, and also that Nynens would receive stock options or
comparable equity awards representing three percent (3%) of the outstanding
equity of the Company;

WHEREAS, on December 20, 2019, Nynens submitted a notice of intent to nominate
director candidates (the “Stockholder Nomination”) for election at the 2020
annual meeting of stockholders of Wayside (the “2020 Annual Meeting”);

WHEREAS, on or about January 22, 2020, the Company received a stockholder demand
letter (the “Demand Letter”): (a) alleging that Nynens had breached the
Separation Agreement by seeking future employment with the Company via the Group
Agreement and by sharing the Company’s confidential information with SKK and N&W
and that SKK and N&W participated in the breach of the Separation Agreement by
Nynens (the “Derivative Allegations”); and (b)

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demanding that the Company investigate the Derivative Allegations and seek,
among other things, a commitment from Nynens to comply with and stop breaching
the Separation Agreement and the return of the Separation Benefits paid in full
to Nynens, including the Equity Benefits (the “Benefit Forfeiture Demand”);

WHEREAS, after independently investigating the Derivative Allegations, the
Company served Nynens, SKK and N&W with cease and desist letters on or about
February 12, 2020: (a) asserting that Nynens had breached the Separation
Agreement and that SKK and N&W had tortious interference with the Separation
Agreement in connection with the Group Agreement; and (b) making the Benefit
Forfeiture Demand;

WHEREAS, on or about February 14, 2020, the Company filed a complaint against
Nynens, SKK, and N&W in the Superior Court of New Jersey Monmouth County (the
“Litigation”): (a) asserting claims against Nynens for alleged breaches of the
Separation Agreement and for declaratory judgment, as well as claims against SKK
and N&W for allegedly tortiously interfering with the Separation Agreement; and
(b) making the Benefit Forfeiture Demand;

WHEREAS, Nynens, SKK, and N&W have denied and continue to deny any wrongdoing or
liability whatsoever as to Wayside’s claims in the Litigation;

WHEREAS, the SKK Parties have, among other things, agreed to terminate the Group
Agreement and Nynens has, among other things, agreed to withdraw the Stockholder
Nomination and to refrain from submitting any director nominations and
stockholder proposals during the Standstill Period (as defined below);

WHEREAS, Nynens and the SKK Parties beneficially own 261,631 shares of Wayside’s
Common Stock, as of the Effective Date; and

WHEREAS, in order to avoid the uncertainty and inconvenience of litigation,
Wayside, Nynens and the SKK Parties wish to settle Wayside’s claims related to
the Litigation on the terms set forth in this Agreement.

NOW, THEREFORE, in consideration of the promises, representations and mutual
covenants and agreements set forth herein, and for other good and valuable
consideration, the receipt and sufficiency of which are hereby acknowledged, the
Parties hereby agree as follows:

1.         Termination of the Group Agreement.  As of the Effective Date,
Nynens, SKK and N&W hereby terminate the Group Agreement, pursuant to Section
10(i) of the Group Agreement, which provides for termination by mutual written
agreement. Within two (2) business days following the Effective Date, SKK and
N&W shall disclose such termination in the SKK Schedule 13D Amendment (as
defined below), and Nynens shall disclose such termination in the Nynens
Schedule 13D Amendment (as defined below), and in each case, append the written
agreement as an exhibit thereto.

2.         Termination of Joint Filing Agreement.3.   As of the Effective Date,
the SKK Parties hereby terminate the Joint Filing Agreement, dated November 27,
2019, by and between the SKK Parties and, within two (2) business days following
the Effective Date, shall disclose such

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termination in the SKK Schedule 13D Amendment and append any applicable
termination agreement as an exhibit thereto.

3.         Withdrawal of Proxy Contest. As of the Effective Date, Nynens hereby
irrevocably agrees to take all necessary actions:

(a)        to withdraw the Stockholder Nomination and any and all related
materials and notices submitted to the Company in connection therewith or
related thereto and any solicitation materials concerning the foregoing or
otherwise related to the 2020 Annual Meeting and filed by or on behalf of Nynens
with the Securities and Exchange Commission (the “SEC”) or furnished to
stockholders of the Company and agrees not to take any further action in
connection with the solicitation of proxies in connection with the Stockholder
Nomination (other than in connection with such withdrawal or Sections 1, 2, 13
hereof); and

(b)        to immediately cease any and all solicitation and other activities in
connection with the 2020 Annual Meeting (it being understood and agreed that
Nynens and the SKK Parties are required to vote their own shares of Common Stock
at the 2020 Annual Meeting, subject to the provisions of this Agreement).

4.         Mutual Non-Disparagement.

(a)        Subject to Section 9, each SKK Party agrees that, from the Effective
Date until the Termination Date (the “Standstill Period”), neither it nor any of
its Representatives (as defined below) shall, and it shall cause each of its
Representatives not to, directly or indirectly, in any way publicly criticize,
disparage, call into disrepute or otherwise defame or slander, Wayside or any of
its Representatives, or any of their respective businesses, products or
services.

(b)        Nynens hereby agrees that, during the Standstill Period, neither he
nor any of his Representatives shall, and he shall cause each of his
Representatives not to, directly or indirectly, in any way publicly criticize,
disparage, call into disrepute or otherwise defame or slander, Wayside or any of
its Representatives, or any of their respective businesses, products or
services.

(c)        Wayside hereby agrees that, during the Standstill Period, neither it
nor any of its Representatives shall, and it shall cause each of its
Representatives not to, directly or indirectly, in any way publicly criticize,
disparage, call into disrepute or otherwise defame or slander, Nynens, any SKK
Party or any of their respective Representatives, or any of their respective
businesses, products or services.

(d)        Notwithstanding the foregoing, nothing in this Section 4 or elsewhere
in this Agreement shall prohibit any Party from making any statement or
disclosure required under the federal securities laws or other applicable laws
(including to comply with any subpoena or other legal process from any
governmental or regulatory authority with competent jurisdiction over the
relevant Party hereto, including without limitation official request for
information, formal inquiry, or examination) or stock exchange regulations;
provided, however, that, unless prohibited under applicable law, such Party must
provide

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written notice to the other Parties prior to making any such statement or
disclosure required under the federal securities laws or other applicable laws
or stock exchange regulations that would otherwise be prohibited by the
provisions of this Section 4, and reasonably consider any comments of such other
Party.

(e)        The limitations set forth in Sections 4(a), 4(b) and 4(c) shall not
prevent any Party from responding to any public statement made by the other
Party of the nature described in Sections 4(a), 4(b) and 4(c), if such statement
by the other Party was made in breach of this Agreement. This Section 4 will not
apply to any truthful statement made in connection with any action to enforce
this Agreement

5.         Share Repurchase. As promptly as practicable, but in any event no
later than five (5) business days after the Effective Date, in full satisfaction
of the Benefit Forfeiture Demand asserted in the Litigation and in exchange for
the releases from Nynens and the SKK parties set forth in Section 7(b) of this
Agreement, and with each Party paying its own fees and expenses, Nynens hereby
sells, assigns, transfers, conveys and delivers to the Company, and the Company
hereby purchases, acquires and accepts for cash all of Nynens’ shares of Common
Stock owned, of record or beneficially, as of the Effective Date (the “Shares”),
including the Equity Benefits, totaling 261,631 Shares (the “Share Repurchase”).
The price of the Share Repurchase shall be set by calculating the VWAP (as
defined below) of the Shares traded on the NASDAQ-GM for the ten (10) trading
days ending on the close of the trading day immediately preceding the Effective
Date.

6.         No Litigation.

(a)        Nynens covenants and agrees that, during the Standstill Period, he
shall not, and shall not permit any of his Representatives to, alone or in
concert with others, knowingly encourage or pursue, or knowingly assist any
other person to threaten, initiate or pursue, any lawsuit, claim or proceeding
(including commencing, encouraging or supporting any derivative action in the
name of Wayside or any class action against Wayside or any of its officers or
directors, in each case with the intent of circumventing any terms of this
Agreement) before any court or governmental, administrative or regulatory body
(collectively, “Legal Proceeding”) arising out of any facts known to Nynens as
of the Effective Date against Wayside or any of its Representatives, except for
any Legal Proceeding initiated solely to remedy a breach of or to enforce this
Agreement; provided, however, that the foregoing shall not prevent Nynens or any
of his Representatives from responding to oral questions, interrogatories,
requests for information or documents, subpoenas, civil investigative demands or
similar processes (a “Legal Requirement”) in connection with any Legal
Proceeding if such Legal Proceeding has not been initiated by, or on behalf of,
Nynens or any of his Representatives; provided, further, that in the event that
Nynens or any of his Representatives receives such Legal Requirement, Nynens
shall, unless prohibited by applicable law, give prompt written notice of such
Legal Requirement to Wayside. In any such Legal Proceeding permitted under this
Section 6(a) by Nynens against Wayside or any of its Representatives, the
prevailing party shall be entitled to an award of all reasonable costs and
attorney’s fees.

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(b)        The SKK Parties covenant and agree that, during the Standstill
Period, they shall not, and shall not permit any of their Representatives to,
alone or in concert with others, knowingly encourage or pursue, or knowingly
assist any other person to threaten, initiate or pursue, any Legal Proceeding
arising out of any facts known to the SKK Parties as of the Effective Date
against Wayside or any of its Representatives, except for any Legal Proceeding
initiated solely to remedy a breach of or to enforce this Agreement; provided,
however, that the foregoing shall not prevent the SKK Parties or any of their
respective Representatives from responding to a Legal Requirement in connection
with any Legal Proceeding if such Legal Proceeding has not been initiated by, or
on behalf of, the SKK Parties or any of their Representatives; provided,
further, that in the event that any of the SKK Parties or any of their
Representatives receives such Legal Requirement, the SKK Parties shall, unless
prohibited by applicable law, give prompt written notice of such Legal
Requirement to Wayside. In any such Legal Proceeding permitted under this
Section 6(b) by the SKK Parties against Wayside or any of its Representatives,
the prevailing party shall be entitled to an award of all reasonable costs and
attorney’s fees.

(c)        Wayside covenants and agrees that, during the Standstill Period, it
shall not, and shall not permit any of its Representatives to, alone or in
concert with others, knowingly encourage or pursue, or knowingly assist any
other person to threaten, initiate or pursue, any Legal Proceedings on claims
arising out of any facts known to Wayside as of the Effective Date against
Nynens or any of the SKK Parties or any of their respective Representatives,
except for any Legal Proceeding initiated solely to remedy a breach of or to
enforce this Agreement; provided, however, that the foregoing shall not prevent
Wayside or any of its Representatives from responding to a Legal Requirement in
connection with any Legal Proceeding if such Legal Proceeding has not been
initiated by, or on behalf of, Wayside or any of its Representatives; provided,
further, that in the event Wayside or any of its Representatives receives such
Legal Requirement, Wayside shall, unless prohibited by applicable law, give
prompt written notice of such Legal Requirement to Nynens or the SKK Parties, as
applicable. In any such Legal Proceeding permitted under this Section 6(c) by
Wayside against Nynens or the SKK Parties, as applicable, or any of their
respective Representatives, the prevailing party shall be entitled to an award
of all reasonable costs and attorney’s fees.

7.         Releases.

(a)        As of the Effective Date, the Company, on behalf of itself and each
of the Company’s Affiliates, permanently, fully and completely releases, acquits
and discharges Nynens and the SKK Parties collectively, separately and
severally, of and from any and all claims (including derivative claims),
demands, damages, causes of action, debts, liabilities, controversies, judgments
and suits of every kind and nature whatsoever, foreseen, unforeseen, known or
unknown, that the Company has had, now has, or may have against Nynens and/or
the SKK Parties collectively, separately and severally, at any time prior to and
including the Effective Date, including (but not limited to) any and all claims
arising out of or in any way whatsoever related to the facts and allegations
asserted in the Litigation, or otherwise related to the Derivative Allegations
and/or Benefit Forfeiture Demand; provided, however, that nothing contained
herein shall operate to release any obligations arising hereunder.

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(b)        As of the Effective Date, Nynens and the SKK Parties permanently,
fully and completely release, acquit and discharge the Company, and the
Company’s subsidiaries, joint ventures and partnerships, successors, assigns,
officers, directors, partners, members, managers, principals, predecessor
entities, agents, employees, stockholders, advisors, consultants, attorneys,
insurers, heirs, executors, administrators, successors and assigns of any such
person or entity (in each case, and in their capacities as such) (collectively,
the “Company’s Affiliates”), collectively, separately and severally, of and from
any and all claims, demands, damages, causes of action, debts, liabilities,
controversies, judgments and suits of every kind and nature whatsoever,
foreseen, unforeseen, known or unknown, that Nynens and the SKK Parties have
had, now have, or may have against the Company and/or the Company’s Affiliates,
collectively, separately and severally, at any time prior to and including the
Effective Date, including (but not limited to) any and all claims arising out of
or in any way whatsoever related to the facts and allegations asserted in the
Litigation, or otherwise related to the Derivative Allegations and/or Benefit
Forfeiture Demand; provided, however, that nothing contained herein shall
operate to release any obligations arising hereunder.

8.         Voluntary Dismissal of the Litigation. In consideration of the terms
set forth herein, including but not limited to the Share Repurchase and the
releases set forth in Section 7, Wayside shall voluntarily dismiss the
Litigation in its entirety with prejudice pursuant to New Jersey Court Rule
4:37-1 within two (2) business days of receiving written confirmation from
Nynens, SKK, and N&W that the Group Agreement has been terminated.

9.         Standstill.

(a)        During the Standstill Period, Nynens and each SKK Party shall not,
and shall cause their respective Representatives not to, directly or indirectly:

(i)         make any announcement or proposal with respect to, or offer, seek,
propose or indicate an interest in, (A) any form of business combination or
acquisition or other transaction relating to some or all of the Common Stock, or
some or all of the material assets of Wayside or any of its subsidiaries, (B)
any form of restructuring, recapitalization or similar transaction with respect
to Wayside or any of its subsidiaries or (C) any form of tender or exchange
offer for shares of Common Stock or other Voting Securities, whether or not such
transaction involves a Change of Control (as defined below) of Wayside; it being
understood that the foregoing shall not prohibit Nynens, the SKK Parties or
their respective Affiliates from acquiring Voting Securities within the
limitations set forth in Section 9(a)(iii), provided, however, that such Parties
may make any announcement or proposal as described in subsections (A), (B) or
(C) above, so long as such announcement or proposal is made privately to the
Company in a manner that would not be reasonably likely to trigger public
disclosure obligations for any Party;

(ii)        engage in, or assist in the engagement in, any solicitation of
proxies or written consents to vote any Voting Securities, or conduct, or assist
in the conducting of, any type of binding or nonbinding referendum with respect
to any Voting Securities, or assist or participate in any other way, directly or
indirectly, in

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any solicitation of proxies (or written consents) with respect to, or from the
holders of, any Voting Securities, or otherwise become a “participant” in a
“solicitation,” as such terms are defined in Instruction 3 of Item 4 of Schedule
14A and Rule 14a-1 of Regulation 14A, respectively, under the Exchange Act, to
vote any securities of Wayside (including by initiating, encouraging or
participating in any “withhold” or similar campaign);

(iii)       purchase or otherwise acquire, or offer, seek, propose or agree to
acquire, ownership (including beneficial ownership) of any securities of
Wayside, any direct or indirect rights or options to acquire any such
securities, any derivative securities or contracts or instruments in any way
related to the price of shares of Common Stock, or any assets or liabilities of
Wayside, except as provided in Section 9(a)(i)(C) and other than by virtue of
passive investments in mutual funds, hedge funds or other pooled investment
vehicles or managed accounts (but not investments in the manager of such funds
or accounts), in each case over which such party does not exercise investment
control;

(iv)       advise, encourage or influence any person with respect to the voting
of (or execution of a written consent in respect of) or disposition of any
securities of Wayside;

(v)        sell, offer or agree to sell directly or indirectly, through swap or
hedging transactions or otherwise, the securities of Wayside or any rights
decoupled from the underlying securities held by Nynens or any of the SKK
Parties to any person not (A) a party to this Agreement, (B) a member of the
Board, (C) an officer of Wayside, or (D) an Affiliate of any Party (any person
not set forth in clauses (A) through (D) shall be referred to as a “Third
Party”) that would knowingly (after due inquiry) result in such Third Party,
together with its Affiliates, owning, controlling or otherwise having any
beneficial or other ownership interest representing in the aggregate in excess
of 4.9% of the shares of Voting Securities outstanding at such time, except for
Schedule 13G filers that are mutual funds, pension funds, index funds or
investment fund managers with no known history of activism or known plans to
engage in activism;

(vi)       take any action in support of or make any proposal or request that
constitutes or would result in: (A) advising, controlling, changing or
influencing any director or the management of Wayside, including, but not
limited to, any plans or proposals to change the number Wayside term of
directors or to fill any vacancies on the Board, except as set forth in this
Agreement, (B) any material change in the capitalization, stock repurchase
programs and practices or dividend policy of Wayside, (C) any other material
change in Wayside’s management, business or corporate structure, (D) seeking to
have Wayside waive or make amendments or modifications to the Bylaws or the
Certificate of Incorporation (each as defined below), or other actions that may
impede or facilitate the acquisition of control of Wayside by any person, (E)
causing a class of securities of Wayside to be delisted from, or to cease to be
authorized to be quoted on, any securities exchange, or (F)

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causing a class of securities of Wayside to become eligible for termination of
registration pursuant to Section 12(g)(4) of the Exchange Act;

(vii)      communicate with stockholders of Wayside or others pursuant to Rule
14a-1(l)(2)(iv) under the Exchange Act;

(viii)     engage in any course of conduct with the purpose of causing
stockholders of Wayside to vote contrary to the recommendation of the Board on
any matter presented to Wayside’s stockholders for their vote at any meeting of
Wayside’s stockholders or by written consent;

(ix)       act, including by making public announcements or speaking to
reporters or members of the media (whether “on the record” or on “background” or
“off the record”), to seek to influence Wayside’s stockholders, management or
the Board with respect to Wayside’s policies, operations, balance sheet, capital
allocation, marketing approach, business configuration, Extraordinary
Transactions, or strategy or to obtain representation on the Board or seek the
removal of any director in any manner, except as expressly permitted by this
Agreement;

(x)        call or seek to call, or request the call of, alone or in concert
with others, any meeting of stockholders, whether or not such a meeting is
permitted by the Bylaws, including a “town hall meeting”;

(xi)       deposit any shares of Common Stock or other Voting Securities in any
voting trust or subject any shares of Common Stock or other Voting Securities to
any arrangement or agreement with respect to the voting of any shares of Common
Stock or Voting Securities (other than any such voting trust, arrangement or
agreement solely among the SKK Parties that is otherwise in accordance with this
Agreement);

(xii)      seek, or encourage or advise any person, to submit nominations in
furtherance of a “contested solicitation” for the election or removal of
directors with respect to Wayside or seek, encourage or take any other action
with respect to the election or removal of any directors;

(xiii)     form, join, maintain or in any other way participate in any “group”
(within the meaning of Section 13(d)(3) of the Exchange Act) with respect to any
Voting Security;

(xiv)     demand a copy of Wayside’s list of stockholders or its other books and
records or make any request pursuant to Rule 14a-7 under the Exchange Act or
under any statutory or regulatory provisions of Delaware providing for
stockholder access to books and records (including lists of stockholders) of
Wayside;

(xv)      make any request or submit any proposal to amend or waive the terms of
this Section 9 other than through non-public communications with

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Wayside that would not be reasonably likely to trigger public disclosure
obligations for any Party;

(xvi)     engage any private investigations firm or other person to investigate
any of Wayside’s directors or officers;

(xvii)    disclose in a manner that could reasonably be expected to become
public any intent, purpose, plan or proposal with respect to any director or the
Company’s management, policies, strategy, operations, financial results or
affairs, any of its securities or assets or this Agreement that is inconsistent
with the provisions of this Agreement; or

(xviii)   enter into any discussions, negotiations, agreements or understandings
with any person with respect to any action Nynens or the SKK Parties are
prohibited from taking pursuant to this Section 9, or advise, assist, knowingly
encourage or seek to persuade any person to take any action or make any
statement with respect to any such action, or otherwise take or cause any action
or make any statement inconsistent with any of the foregoing.

Notwithstanding anything to the contrary contained in this Section 9, Nynens and
the SKK Parties shall not be prohibited or restricted from: (A) communicating
privately with the Board or any officer or director of Wayside, in the manner
set forth for communicating with the Company in the Company Policies (as defined
below), regarding any matter, so long as such communications are not intended
to, and would not reasonably be expected to, require any public disclosure of
such communications by Nynens, any of the SKK Parties or their respective
Affiliates, Wayside or its Affiliates or any Third Party, subject in any case to
any confidentiality obligations to Wayside of any such director or officer and
applicable law, rules or regulations; (B) taking any action necessary to comply
with any law, rule or regulation or any action required by any governmental or
regulatory authority or stock exchange that has, or may have, jurisdiction over
Nynens or any SKK Party, provided that a breach by such Parties of this
Agreement is not the cause of the applicable requirement; or (C) privately
communicating to any of their potential investors or investors factual
information regarding Wayside, provided such communications are subject to
reasonable confidentiality obligations and are not otherwise reasonably expected
to be publicly disclosed.

(b)        The provisions of this Section 9 shall not limit in any respect the
actions of any director of Wayside in his or her capacity as such, recognizing
that such actions are subject to such director’s fiduciary duties to Wayside and
its stockholders and the Company Policies.  The provisions of this Section 9
shall also not prevent Nynens or the SKK Parties from freely voting their
respective shares of Common Stock.

(c)        During the Standstill Period, Nynens and each SKK Party shall refrain
from taking any actions which could have the effect of encouraging, assisting or
influencing other stockholders of Wayside or any other persons to engage in
actions which, if taken by such Party, would violate this Agreement.

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(d)        Notwithstanding anything contained in this Agreement to the contrary,
the provisions of Section 4 of this Agreement shall automatically terminate upon
the consummation of a Change of Control transaction agreed to by the Board and
involving Wayside if the acquiring or counter-party to the Change of Control
transaction has conditioned the closing of the transaction on the termination of
such sections.

(e)        During the Standstill Period, Nynens agrees not to, and to cause his
Representatives not to, comment publicly about any director or the Company’s
management, policies, strategy, operations, financial results or affairs or any
transactions involving Wayside or any of its subsidiaries, except as expressly
permitted by this Agreement.

10.       Representations and Warranties of Wayside.  Wayside represents and
warrants to Nynens and the SKK Parties that (a) Wayside has the corporate power
and authority to execute this Agreement and to bind it thereto, (b) this
Agreement has been duly and validly authorized, executed and delivered by
Wayside, constitutes a valid and binding obligation and agreement of Wayside,
and is enforceable against Wayside in accordance with its terms, except as
enforcement thereof may be limited by applicable bankruptcy, insolvency,
reorganization, moratorium, fraudulent conveyance or similar laws generally
affecting the rights and remedies of creditors and subject to general equity
principles, and (c) the execution, delivery and performance of this Agreement by
Wayside does not and will not violate or conflict with (i) any law, rule,
regulation, order, judgment or decree applicable to it, or (ii) result in any
breach or violation of or constitute a default (or an event which with notice or
lapse of time or both could become a default) under or pursuant to, or result in
the loss of a material benefit under, or give any right of termination,
amendment, acceleration or cancellation of, any organizational document, or any
material agreement, contract, commitment, understanding or arrangement to which
Wayside is a party or by which it is bound.

11.       Representations and Warranties of Nynens.  Nynens represents and
warrants to Wayside and the SKK Parties that (a) this Agreement has been duly
and validly authorized, executed and delivered by Nynens, and constitutes a
valid and binding obligation and agreement of Nynens, enforceable against Nynens
in accordance with its terms, except as enforcement thereof may be limited by
applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent
conveyance or similar laws generally affecting the rights and remedies of
creditors and subject to general equity principles, (b) Nynens has the power and
authority to execute this Agreement and any other documents or agreements
entered into in connection with this Agreement on behalf of himself, and to bind
Nynens to the terms hereof and thereof, and (c) the execution, delivery and
performance of this Agreement by Nynens does not and will not violate or
conflict with (i) any law, rule, regulation, order, judgment or decree
applicable to it, or (ii) result in any breach or violation of or constitute a
default (or an event which with notice or lapse of time or both could become a
default) under or pursuant to, or result in the loss of a material benefit
under, or give any right of termination, amendment, acceleration or cancellation
of, any organizational document, agreement, contract, commitment, understanding
or arrangement to which such member is a party or by which it is bound.

12.       Representations and Warranties of the SKK Parties.  Each SKK Party
jointly and severally represents and warrants to Wayside and Nynens that (a)
this Agreement has been duly

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and validly authorized, executed and delivered by such SKK Party, and
constitutes a valid and binding obligation and agreement of such SKK Party,
enforceable against such SKK Party in accordance with its terms, except as
enforcement thereof may be limited by applicable bankruptcy, insolvency,
reorganization, moratorium, fraudulent conveyance or similar laws generally
affecting the rights and remedies of creditors and subject to general equity
principles, (b) the signatory for such SKK Party has the power and authority to
execute this Agreement and any other documents or agreements entered into in
connection with this Agreement on behalf of itself and the applicable SKK Party
associated with that signatory’s name, and to bind such SKK Party to the terms
hereof and thereof, and (c) the execution, delivery and performance of this
Agreement by such SKK Party does not and will not violate or conflict with (i)
any law, rule, regulation, order, judgment or decree applicable to it, or (ii)
result in any breach or violation of or constitute a default (or an event which
with notice or lapse of time or both could become a default) under or pursuant
to, or result in the loss of a material benefit under, or give any right of
termination, amendment, acceleration or cancellation of, any organizational
document, agreement, contract, commitment, understanding or arrangement to which
such member is a party or by which it is bound.

13.       SEC Filings.

(a)        No later than two (2) business days following the Effective Date,
Wayside shall file with the SEC a Current Report on Form 8-K reporting its entry
into this Agreement and appending this Agreement as an exhibit thereto (the
“Form 8-K”). The Form 8-K shall be consistent with the terms of this Agreement.
Wayside shall provide Nynens and the SKK Parties with a reasonable opportunity
to review and comment on the Form 8-K prior to the filing with the SEC and
consider in good faith any comments of Nynens and the SKK Parties.

(b)        No later than two (2) business days following the Effective Date,
Nynens shall file with the SEC an amendment to that certain Schedule 13D, filed
with the SEC on June 17, 2019 and amended on November 27, 2019, December 12,
2019, and December 20, 2019 (collectively, the “Nynens Schedule 13D”), in
compliance with Section 13 of the Exchange Act reporting his entry into this
Agreement and appending this Agreement as an exhibit thereto or incorporating
this Agreement by reference to Wayside’s Current Report on Form 8-K referred to
in Section 13(a) hereof (the “Nynens Schedule 13D Amendment”).  The Nynens
Schedule 13D Amendment shall be consistent with the terms of this Agreement.
Nynens shall provide Wayside with a reasonable opportunity to review and comment
on the Nynens Schedule 13D Amendment prior to it being filed with the SEC and
consider in good faith any comments of Wayside.

(c)        No later than two (2) business days following the Effective Date, the
SKK Parties shall file with the SEC an amendment to that certain Schedule 13D,
filed with the SEC on November 27, 2019 and amended on December 11, 2019 and
December 23, 2019 (collectively, the “SKK Schedule 13D”), in compliance with
Section 13 of the Exchange Act reporting their entry into this Agreement and
appending this Agreement as an exhibit thereto or incorporating this Agreement
by reference to Wayside's Current Report on Form 8-K referred to in Section
13(a) hereof (the “SKK Schedule 13D Amendment”).  The SKK Schedule 13D Amendment
shall be consistent with the terms of this Agreement. The SKK Parties shall
provide Wayside with a reasonable opportunity to review and comment

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on the SKK Schedule 13D Amendment prior to it being filed with the SEC and
consider in good faith any comments of Wayside.

(d)        Except as otherwise provided in this Section 13 and/or Section 4(d),
the SKK Parties shall not make any public statements related to this Agreement.

14.       Term; Termination.  The term of this Agreement shall commence on the
Effective Date and shall continue until December 31, 2022 (the “Termination
Date”); provided, however, that (a) Nynens or the SKK Parties may earlier
terminate this Agreement if Wayside commits a material breach of its obligations
under this Agreement that (if capable of being cured) is not cured within
fifteen (15) days after receipt by Wayside from such Party specifying the
material breach, or, if impossible to cure within fifteen (15) days, that
Wayside has not taken any substantive action to cure within such fifteen
(15)-day period, and (b) Wayside may earlier terminate this Agreement if Nynens
or any of the SKK Parties commits a material breach of this Agreement that (if
capable of being cured) is not cured within fifteen (15) days after receipt by
such Party from Wayside specifying the material breach, or, if impossible to
cure within fifteen (15) days, that such Party has not taken any substantive
action to cure within such fifteen (15)-day period. Termination of this
Agreement shall not relieve any Party from its responsibilities in respect of
any breach of this Agreement prior to such termination. Section 7 hereof shall
survive termination of this Agreement indefinitely.

15.       Expenses.  Except as may be otherwise separately agreed as between the
SKK Parties and Nynens, each Party shall be responsible for its own fees and
expenses in connection with the negotiation and execution of this Agreement and
the transactions contemplated hereby.

16.       No Other Discussions or Arrangements.  Nynens and the SKK Parties
represent and warrant that, as of the date of this Agreement, except as
specifically disclosed on the Nynens Schedule 13D, the SKK Schedule 13D, or as
disclosed to Wayside in writing prior to the Effective Date, (a) none of Nynens
or the SKK Parties owns, of record or beneficially, any Voting Securities or any
securities convertible into, or exchangeable or exercisable for, any Voting
Securities and (b) none of Nynens of the SKK Parties have entered into, directly
or indirectly, any agreements or understandings with any person (other than
their own respective Representatives) with respect to any potential transaction
involving Wayside or the voting or disposition of any securities of Wayside.

17.       Governing Law; Jurisdiction.  This Agreement shall be governed by and
construed in accordance with the internal laws of the State of Delaware without
giving effect to any choice or conflict of law provision or rule that would
cause the application of laws of any jurisdiction other than those of the State
of Delaware. Each Party agrees that it shall bring any suit, action or other
proceeding in respect of any claim arising out of or related to this Agreement
(each, an “Action”) exclusively in (a) the Delaware Court of Chancery in and for
New Castle County, (b) in the event (but only in the event) that such court does
not have subject matter jurisdiction over such Action, the United States
District Court for the District of Delaware or (c) in the event (but only in the
event) such courts identified in clauses (a) and (b) do not have subject matter
jurisdiction over such Action, any other Delaware state court (collectively, the
“Chosen Courts”), and, solely in connection with an Action, (i) irrevocably
submits to the exclusive jurisdiction of the Chosen Courts, (ii) irrevocably
submits to the exclusive venue of any such Action in the

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Chosen Courts and waives any objection to laying venue in any such Action in the
Chosen Courts, (iii) waives any objection that the Chosen Courts are an
inconvenient forum or do not have jurisdiction over any Party hereto and (iv)
agrees that service of process upon such Party in any such Action shall be
effective if notice is given in accordance with Section 21 of this Agreement.
 Each Party agrees that a final judgment in any Action brought in the Chosen
Courts shall be conclusive and binding upon each of the Parties and may be
enforced in any other courts, the jurisdiction of which each of the Parties is
or may be subject, by suit upon such judgment.

18.       Waiver of Jury Trial.  EACH PARTY HERETO ACKNOWLEDGES AND AGREES THAT
ANY CONTROVERSY WHICH MAY ARISE UNDER THIS AGREEMENT IS LIKELY TO INVOLVE
COMPLICATED AND DIFFICULT ISSUES AND, THEREFORE, EACH SUCH PARTY IRREVOCABLY AND
UNCONDITIONALLY WAIVES TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW ANY
RIGHT IT MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LEGAL ACTION ARISING OUT
OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED BY THIS
AGREEMENT.  EACH PARTY TO THIS AGREEMENT CERTIFIES AND ACKNOWLEDGES THAT (A) NO
REPRESENTATIVE OF ANY OTHER PARTY HERETO HAS REPRESENTED, EXPRESSLY OR
OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT SEEK TO ENFORCE THE FOREGOING WAIVER
IN THE EVENT OF A LEGAL ACTION, (B) SUCH PARTY HAS CONSIDERED THE IMPLICATIONS
OF THIS WAIVER, (C) SUCH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (D) SUCH PARTY
HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL
WAIVERS AND CERTIFICATIONS IN THIS SECTION 18.

19.       Specific Performance.  Each of the Parties acknowledges and agrees
that irreparable injury to the other Parties would occur in the event any of the
provisions of this Agreement are not performed in accordance with their specific
terms or are otherwise breached and that such injury would not be adequately
compensable by the remedies available at law (including the payment of money
damages).  It is accordingly agreed that each of the Parties (the “Moving
Party”) shall be entitled to specific enforcement of, and injunctive or other
equitable relief as a remedy for any such breach or to prevent any violation or
threatened violation of, the terms hereof, and the other Parties will not take
action, directly or indirectly, in opposition to the Moving Party seeking such
relief on the grounds that any other remedy or relief is available at law or in
equity.  The Parties further agree to waive any requirement for the security or
posting of any bond in connection with any such relief.  The remedies available
pursuant to this Section 19 shall not be deemed to be the exclusive remedies for
a breach of this Agreement but shall be in addition to all other remedies
available at law or equity.

20.       Certain Definitions. As used in this Agreement:

(a)        “Affiliate” shall mean any “Affiliate” as defined in Rule 12b-2
promulgated by the SEC under the Exchange Act, including, for the avoidance of
doubt, persons who become Affiliates subsequent to the Effective Date;

(b)        “Associate” shall mean any “Associate” as defined in Rule 12b-2
promulgated by the SEC under the Exchange Act, including, for the avoidance of
doubt, persons who become Associates subsequent to the Effective Date;

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(c)        “beneficial owner”, “beneficial ownership” and “beneficially own”
shall have the same meanings as set forth in Rule 13d-3 promulgated by the SEC
under the Exchange Act;

(d)        “business day” shall mean any day other than a Saturday, Sunday or
day on which the commercial banks in the State of New York are authorized or
obligated to be closed by applicable law;

(e)        “Bylaws” shall mean the Restated Bylaws of the Company, as adopted
July 5, 1995, and as may be further amended from time to time;

(f)        “Certificate of Incorporation” shall mean the Restated Certificate of
Incorporation of the Company, as amended by the Certificate of Amendment dated
August 8, 2005, and as may be further amended from time to time;

(g)        a “Change of Control” transaction shall be deemed to have taken place
if (i) any person is or becomes a beneficial owner, directly or indirectly, of
securities of Wayside representing more than fifty percent (50%) of the equity
interests and voting power of Wayside’s then-outstanding equity securities or
(ii) Wayside enters into a stock-for-stock transaction whereby immediately after
the consummation of the transaction Wayside’s stockholders retain less than
fifty percent (50%) of the equity interests and voting power of the surviving
entity’s then-outstanding equity securities;

(h)        “Company Policies” mean the policies, processes, procedures, codes,
rules, standards and guidelines applicable to members of the Board, including,
but not limited to, Wayside’s Code of Ethics and Business Conduct &
Anti-Corruption Policies, Fair Disclosure Policy, and any other policies on
stock ownership, public disclosures and confidentiality.

(i)         “Board” shall mean the Company’s Board of Directors;

(j)         “Extraordinary Transaction” shall mean any equity tender offer,
equity exchange offer, merger, acquisition, business combination, or other
transaction with a Third Party that, in each case, would result in a Change of
Control of Wayside, liquidation, dissolution or other extraordinary transaction
involving a majority of its equity securities or a majority of its assets, and,
for the avoidance of doubt, including any such transaction with a Third Party
that is submitted for a vote of Wayside’s stockholders;

(k)        “other Parties” shall mean, (i) with respect to Wayside, Nynens and
any of the SKK Parties, (ii) with respect to Nynens, Wayside and any of the SKK
Parties, and (c) with respect to any of the SKK Parties, Wayside and Nynens;

(l)         “person” or “persons” shall mean any individual, corporation
(including not-for-profit), general or limited partnership, limited liability
company, joint venture, estate, trust, association, organization or other entity
of any kind, structure or nature;

(m)       “Representative” shall mean a person’s Affiliates and Associates and
its and their respective directors, officers, employees, partners, members,
managers,

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consultants, legal or other advisors, agents and other representatives;
provided, that when used with respect to Wayside, “Representatives” shall not
include any non-executive employees;

(n)        “Voting Securities” means the Common Stock and any other securities
of the Company entitled to vote in the election of directors; and

(o)        “VWAP” means, for any security as of any date, the volume-weighted
average price for such security on the NASDAQ Global Market (or, if the NASDAQ
Global Market is not the principal trading market for such security, then on the
principal securities exchange or securities market on which such security is
then traded), during the period beginning at 9:30 a.m., New York time, and
ending at 4:00 p.m., New York time, as reported by the NASDAQ Global Market. All
such determinations shall be appropriately adjusted for any stock dividend,
stock split, stock combination, recapitalization or other similar transaction
during such period.

21.       Notices. All notices, requests, consents, claims, demands, waivers,
and other communications hereunder shall be in writing and shall be deemed to
have been given: (a) when delivered by hand (with written confirmation of
receipt), (b) when received by the addressee if sent by a nationally recognized
overnight courier (receipt requested), (c) on the date sent by email (with
confirmation of transmission) if sent during normal business hours, and on the
next business day if sent after normal business hours; or (d) on the third day
after the date mailed, by certified or registered mail, return receipt
requested, postage prepaid. Such communications must be sent to the respective
Parties at the addresses set forth in this Section 21 (or to such other address
that may be designated by a Party from time to time in accordance with this
Section 21).

If to Wayside, to its address at:

Wayside Technology Group, Inc.

4 Industrial Way West, 3rd Floor

Eatontown, New Jersey 07724

Attention:

Jeffrey Geygan

Michael Vesey

Email:

Jeff.Geygan@GVI-Corp.com

Michael.Vesey@waysidetechnology.com

With a copy (which shall not constitute notice) to:

Venable LLP

1290 Avenue of the Americas, 20th Floor

New York, New York 10104

Attention:

Kostas D. Katsiris

Elise M. Gabriel

Email:

KDKatsiris@venable.com

EMGabriel@venable.com

If to Nynens, to the address at:

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Simon F. Nijnens

c/o New Jersey Institute of Technology

University Heights

Newark, New Jersey 07102

Email:

simonnynens@gmail.com

With a copy (which shall not constitute notice) to:

Gibbons P.C.

One Pennsylvania Plaza, 37th Floor

New York, New York 10119

Attention:

Frank T. Cannone, Esq.

James J. Petrucci, Esq.

Email:

fcannone@gibbonslaw.com

jpetrucci@gibbonslaw.com

If to an SKK Party, to the addresses at:

Shepherd Kaplan Krochuk, LLC

125 Summer Street, Floor 22

Boston, Massachusetts 02110

Attention: Legal

Email:

legal@skk-llc.com

and

North & Webster SSG, LLC

125 Summer Street, Floor 22

Boston, Massachusetts 02110

Attention: Samuel Kidston

Email:

skidston@northandwebster.com

With a copy (which shall not constitute notice) to:

Olshan Frome Wolosky LLP

1325 Avenue of the Americas

New York, New York 10019

Attention: Andrew M. Freedman

Mohammad Malik

Email:

afreedman@olshanlaw.com

mmalik@olshanlaw.com

22.       Entire Agreement. This Agreement constitutes the sole and entire
agreement of the Parties with respect to the subject matter contained herein,
and supersedes all prior and contemporaneous understandings, agreements,
representations, and warranties, both written and

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oral, with respect to such subject matter. This Agreement may only be amended,
modified, or supplemented by an agreement in writing signed by each Party.

23.       Severability. If any term or provision of this Agreement is invalid,
illegal, or unenforceable in any jurisdiction, such invalidity, illegality, or
unenforceability shall not affect any other term or provision of this Agreement
or invalidate or render unenforceable such term or provision in any other
jurisdiction.

24.       Counterparts. This Agreement may be executed in counterparts, each of
which shall be deemed an original, but all of which together shall be deemed to
be one and the same agreement. A signed copy of this Agreement delivered by
facsimile, email, or other means of electronic transmission shall be deemed to
have the same legal effect as delivery of an original signed copy of this
Agreement.

25.       Assignment. No Party may assign any of its rights or delegate any of
its obligations hereunder without the prior written consent of the other
Parties; provided, that each Party may assign any of its rights and delegate any
of its obligations hereunder to any person or entity that acquires substantially
all of that Party’s assets, whether by stock sale, merger, asset sale or
otherwise. Any purported assignment or delegation in violation of this
Section 25 shall be null and void. No assignment or delegation shall relieve the
assigning or delegating Party of any of its obligations hereunder. This
Agreement is for the sole benefit of the Parties and their respective successors
and permitted assigns and nothing herein, express or implied, is intended to or
shall confer upon any other person or entity any legal or equitable right,
benefit or remedy of any nature whatsoever under or by reason of this Agreement.

26.       Waivers. No waiver by any Party of any of the provisions hereof shall
be effective unless explicitly set forth in writing and signed by the Parties so
waiving. No waiver by any Party shall operate or be construed as a waiver in
respect of any failure, breach, or default not expressly identified by such
written waiver, whether of a similar or different character, and whether
occurring before or after that waiver. No failure to exercise, or delay in
exercising, any right, remedy, power, or privilege arising from this Agreement
shall operate or be construed as a waiver thereof; nor shall any single or
partial exercise of any right, remedy, power, or privilege hereunder preclude
any other or further exercise thereof or the exercise of any other right,
remedy, power, or privilege.

[Remainder of Page Intentionally Left Blank]

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IN WITNESS WHEREOF, the Parties have executed this Agreement to be effective as
of the Effective Date.

WAYSIDE:

WAYSIDE TECHNOLOGY GROUP, INC.

By:

/s/ Michael Vesey

Name:

[Michael Vesey]

Title:

[Principal Accounting Officer and Principal Financial Officer]

Signature Page to Settlement Agreement

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NYNENS:

SIMON F. NIJNENS

/s/ Simon F. Nijnens

Signature Page to Settlement Agreement

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SKK PARTIES:

SHEPHERD KAPLAN KROCHUK, LLC

By:

/s/ Tim Krochuck

Name:

Tim Krochuk

Title:

Tim Krochuk

DAVID SHEPHERD

/s/ David Shepherd

DAVID KAPLAN

/s/ David Kaplan

TIMOTHY KROCHUK

/s/ Timothy Krochuk

NORTH & WEBSTER SSG, LLC

By:

/s/ Samuel A. Kidston

Name:

Samuel A. Kidston

Title:

Managing Member

SAMUEL KIDSTON

/s/ Samuel A. Kidston

DENNIS CROWLEY

/s/ Dennis Crowley

Signature Page to Settlement Agreement

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