Document:

exv10w38

Exhibit 10.38

INDEMNIFICATION AGREEMENT

     THIS INDEMNIFICATION AGREEMENT is made and entered into as of March 14, 2005 (this
“Agreement”), by and between TRUSTWAVE HOLDINGS, INC., a Delaware corporation (the
“Company,” which term shall include, where appropriate, any Entity (as hereinafter defined)
controlled directly or indirectly by the Company), Joseph Patanella and Erik Schetina (the
“TrustWave Directors”), the TrustWave Directors are sometimes referred to herein
collectively as “Indemnitees,” and individually as “Indemnitee”):

     WHEREAS, the Company is a party to that certain Contribution Agreement, dated as of the date
hereof, by and among the Company, TrustWave Corporation, and other investors (the “Contribution
Agreement”);

     WHEREAS, pursuant to the Stockholders Agreement (as defined in the Contribution Agreement),
two (2) directors of the Company shall be nominated by the TrustWave Majority Holders (as defined
in the Contribution Agreement);

     WHEREAS, as a condition to the Contribution Agreement, the Company is required to enter into
this Agreement with Indemnitees;

     WHEREAS, increased corporate litigation has subjected directors and their affiliates to
litigation risks and expenses, and the limitations on the availability of directors and officers
liability insurance have made it increasingly difficult for the Company to attract and retain such
persons;

     WHEREAS, the Company’s Certificate of Incorporation (as the same may be amended and restated
from time to time) requires it to indemnify its directors to the fullest extent permitted by the
Delaware General Corporation Law and permit it to make other indemnification arrangements and
agreements;

     WHEREAS, the Company desires to provide Indemnitees with specific contractual assurance of
Indemnitees’ rights to full indemnification against litigation risks and expenses (regardless,
among other things, of any amendment to or revocation of the Company’s Certificate of Incorporation
and Bylaws, or any change in the composition of its Board of Directors); and

     WHEREAS, the Company intends that this Agreement provide Indemnitees with greater protection
than that which is provided by the Company’s Certificate of Incorporation.

     NOW, THEREFORE, in consideration of the promises and the covenants contained herein, the
Company and Indemnitees do hereby covenant and agree as follows:

 

 

     1. Definitions.

          (a) “Corporate Status” describes the status of (A) an Entity (including its
affiliates) which is nominating or has nominated a director of the Company or (B) a person who is
serving or has served (i) as a director of the Company, (ii) in any capacity with respect to any
employee benefit plan of the Company, or (iii) as a director, partner, trustee, officer, employee
or agent of any other Entity at the request of the Company. For purposes of subsection (iii) of
this Section 1(a), if Indemnitee is serving or has served as a director, partner, trustee, officer,
employee or agent of a Subsidiary, Indemnitee shall be deemed to be serving at the request of the
Company.

          (b) “Entity” shall mean any corporation, partnership, limited liability company, joint
venture, trust, foundation, association, organization or other legal entity.

          (c) “Expenses” shall mean all fees, costs and expenses reasonably incurred by
Indemnitee in connection with any Proceeding (as defined below), including, without limitation,
attorneys’ fees, disbursements and retainers (including, without limitation, any such fees,
disbursements and retainers incurred by Indemnitee pursuant to Sections 9 and 10(c) of this
Agreement), fees and disbursements of expert witnesses and professional advisors (including,
without limitation, accountants), court costs, transcript costs, duplicating, printing and binding
costs, telephone and fax transmission charges, postage, delivery services, and other disbursements
and expenses.

          (d) “Indemnifiable Expenses,” “Indemnifiable Liabilities” and
“Indemnifiable Amounts” shall have the meanings ascribed to those terms in Section 3(a)
below.

          (e) “Liabilities” shall mean judgments, damages, liabilities, losses, penalties,
excise taxes, fines and amounts paid in settlement.

          (f) “Proceeding” shall mean any threatened, pending or completed claim, action, suit,
arbitration, alternate dispute resolution process, investigation, administrative hearing, appeal,
or any other proceeding, whether civil, criminal, administrative, arbitrative or investigative,
whether formal or informal, including a proceeding initiated by any Indemnitee pursuant to Section
9 of this Agreement to enforce Indemnitees’ rights hereunder.

          (g) “Subsidiary” shall mean any corporation, partnership, limited liability company,
joint venture, trust or other Entity of which the Company owns (either directly or through or
together with another Subsidiary of the Company) either (i) a general partner, managing member or
other similar interest or (ii) (A) 50% or more of the voting power of the voting capital equity
interests of such corporation, partnership, limited liability company, joint venture or other
Entity, or (B) 50% or more of the outstanding voting capital stock or other voting equity interests
of such corporation, partnership, limited liability company, joint venture or other Entity.

     2. Services of Indemnitees. In consideration of the Company’s covenants and
commitments hereunder, the TrustWave Directors shall serve as, or continue to serve as, directors
of the Company. However, this Agreement shall not impose any obligation on Indemnitees or the
Company to continue the TrustWave Directors’ service to the Company

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beyond any period otherwise required by law or by other agreements or commitments of the
parties, if any.

     3. Agreement to Indemnify. The Company agrees to indemnify each Indemnitee as
follows:

          (a) Proceedings Other Than By or In the Right of the Company. Subject to the
exceptions contained in Section 4(a) below, if Indemnitee was or is a party or is threatened to be
made a party to any Proceeding (other than an action by or in the right of the Company) by reason
of Indemnitee’s Corporate Status, Indemnitee shall be indemnified by the Company against all
Expenses and Liabilities incurred or paid by Indemnitee in connection with such Proceeding
(referred to herein as “Indemnifiable Expenses” and “Indemnifiable Liabilities,”
respectively, and collectively as “Indemnifiable Amounts”).

          (b) Proceedings By or In the Right of the Company. Subject to the exceptions
contained in Section 4(b) below, if Indemnitee was or is a party or is threatened to be made a
party to any Proceeding by or in the right of the Company by reason of Indemnitee’s Corporate
Status, Indemnitee shall be indemnified by the Company against all Indemnifiable Expenses.

          (c) Conclusive Presumption Regarding Standard of Care. In making any determination
required to be made under Delaware law or other law with respect to entitlement to indemnification
hereunder, the person, persons or entity making such determination shall presume that Indemnitee is
entitled to indemnification under this Agreement if Indemnitee submitted a request therefor in
accordance with Section 5 of this Agreement, and the Company shall have the burden of proof to
overcome that presumption in connection with the making by any person, persons or entity of any
determination contrary to that presumption.

     4. Exceptions to Indemnification. Each Indemnitee shall be entitled to
indemnification under Sections 3(a) and 3(b) above in all circumstances other than with respect to
any specific claim, issue or matter involved in the Proceeding out of which Indemnitee’s claim for
indemnification has arisen, as follows:

          (a) Proceedings Other Than By or In the Right of the Company. If indemnification is
requested under Section 3(a) and it has been finally adjudicated by a court of competent
jurisdiction that, in connection with such specific claim, issue or matter, (A) Indemnitee failed
to act (i) in good faith and (ii) in a manner Indemnitee reasonably believed to be in or not
opposed to the best interests of the Company, or (B) with respect to any criminal action or
proceeding, Indemnitee had reasonable cause to believe that Indemnitee’s conduct was unlawful,
Indemnitee shall not be entitled to payment of Indemnifiable Amounts hereunder.

          (b) Proceedings By or In the Right of the Company. If indemnification is requested
under Section 3(b) and

               (i) it has been finally adjudicated by a court of competent jurisdiction that, in connection
with such specific claim, issue or matter, Indemnitee failed to act (A) in good faith and (B) in a
manner Indemnitee reasonably believed to be in or not opposed to the best interests of the Company,
Indemnitee shall not be entitled to payment of Indemnifiable Expenses hereunder; or

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               (ii) it has been finally adjudicated by a court of competent jurisdiction that Indemnitee is
liable to the Company with respect to such specific claim, no Indemnifiable Expenses shall be paid
with respect to such claim, issue or matter unless a court of competent jurisdiction in which such
Proceeding was brought shall determine upon application that, despite the adjudication of
liability, but in view of all the circumstances of the case, Indemnitee is fairly and reasonably
entitled to indemnification for such Indemnifiable Expenses which such court shall deem proper; or

               (iii) it has been finally adjudicated by a court of competent jurisdiction that Indemnitee is
liable to the Company for an accounting of profits made from the purchase or sale by the Indemnitee
of securities of the Company pursuant to the provisions of Section 16(b) of the Securities Exchange
Act of 1934, the rules and regulations promulgated thereunder and amendments thereto or similar
provisions of any federal, state or local statutory law.

          (c) Insurance Proceeds. To the extent payment is actually made to Indemnitee under a
valid and collectible insurance policy in respect of Indemnifiable Expenses in connection with such
specific claim, issue or matter, Indemnitee shall not be entitled to payment of Indemnifiable
Expenses hereunder except in respect of any excess Indemnifiable Expenses beyond the amount of
payment under such insurance.

     5. Procedure for Payment of Indemnifiable Amounts. Indemnitee shall submit to the
Company a written request specifying the Indemnifiable Amounts for which Indemnitee seeks payment
under Section 3 of this Agreement and the basis for the claim. The Company shall pay such
Indemnifiable Amounts to Indemnitee within sixty (60) calendar days of receipt of the request. At
the request of the Company, Indemnitee shall furnish such documentation and information within
Indemnitee’s control or possession or as is reasonably available to Indemnitee, and necessary to
establish that Indemnitee is entitled to indemnification hereunder.

     6. Indemnification for Expenses of a Party Who is Wholly or Partly Successful.
Notwithstanding any other provision of this Agreement, to the extent that Indemnitee is, by reason
of his Corporate Status, a party to and is successful, on the merits or otherwise, in any
Proceeding, he shall be indemnified to the maximum extent permitted by law, as such may be amended
from time to time, against all Expenses actually and reasonably incurred by him or on his behalf in
connection therewith. If Indemnitee is not wholly successful in such Proceeding but is successful,
on the merits or otherwise, as to one or more but less than all claims, issues or matters in such
Proceeding, the Company shall indemnify Indemnitee against all Expenses actually and reasonably
incurred by him or on his behalf in connection with each successfully resolved claim, issue or
matter. For purposes of this Section and without limitation, the termination of any claim, issue
or matter in such a Proceeding by dismissal, with or without prejudice, shall be deemed to be a
successful result as to such claim, issue or matter.

     7. Effect of Certain Resolutions. Neither the settlement or termination of any
Proceeding nor the failure of the Company to award indemnification or to determine that
indemnification is payable shall create a presumption that an Indemnitee is not entitled to
indemnification hereunder. In addition, the termination of any Proceeding against the Company (and
not the Indemnitee) by judgment, order, settlement, conviction, or upon a plea of nolo contendere
or its equivalent shall not create a presumption that such Indemnitee did not act in

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good faith and in a manner which Indemnitee reasonably believed to be in or not opposed to the
best interests of the Company or, with respect to any criminal action or proceeding, had reasonable
cause to believe that such Indemnitee’s action was unlawful.

     8. Agreement to Advance Expenses; Undertaking. The Company shall advance all Expenses
incurred by or on behalf of Indemnitee in connection with any Proceeding, including a Proceeding by
or in the right of the Company, in which Indemnitee is involved by reason of such Indemnitee’s
Corporate Status within ten (10) calendar days after the receipt by the Company of a written
statement from Indemnitee requesting such advance or advances from time to time, whether prior to
or after final disposition of such Proceeding, upon receipt of an undertaking by Indemnitee to
repay any and all of the amount of Indemnifiable Expenses paid to Indemnitee if it is finally
determined by a court of competent jurisdiction that Indemnitee is not entitled under this
Agreement to indemnification with respect to such Expenses. Such written statement shall specify
the Indemnifiable Expenses for which Indemnitee seeks an advancement under this Agreement, together
with documentation evidencing that Indemnitee has incurred such Indemnifiable Expenses. This
undertaking is an unlimited general obligation of each of Indemnitees.

     9. Remedies of Indemnitee.

          (a) Right to Petition Court. In the event that any Indemnitee makes a request for
payment of Indemnifiable Amounts under Sections 3 and 5 above or a request for an advancement of
Indemnifiable Expenses under Section 8 above and the Company fails to make such payment or
advancement in a timely manner pursuant to the terms of this Agreement, such Indemnitee may
petition the court of competent jurisdiction to enforce the Company’s obligations under this
Agreement.

          (b) Burden of Proof. In any judicial proceeding brought under Section 9(a) above, the
Company shall have the burden of proving that Indemnitee is not entitled to payment of
Indemnifiable Amounts hereunder.

          (c) Expenses. The Company agrees to reimburse Indemnitee in full for any Expenses
incurred by Indemnitee in connection with any action brought by Indemnitee under Section 9(a)
above, or in connection with any claim or counterclaim brought by the Company in connection
therewith, but only in the event that Indemnitee is successful on the merits in connection with any
such action.

          (d) Failure to Act Not a Defense. The failure of the Company (including its Board of
Directors or any committee thereof, independent legal counsel, or stockholders) to make a
determination concerning the permissibility of the payment of Indemnifiable Amounts or the
advancement of Indemnifiable Expenses under this Agreement shall not be a defense in any action
brought under Section 9(a) above, and shall not create a presumption that such payment or
advancement is not permissible.

     10. Defense of the Underlying Proceeding.

          (a) Notice by Indemnitee. Indemnitees agree to notify the Company promptly upon being
served with any summons, citation, subpoena, complaint, indictment, information, or

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other document relating to any Proceeding which may result in the payment of Indemnifiable
Amounts or the advancement of Indemnifiable Expenses hereunder; provided, however,
that the failure to give any such notice shall not disqualify any Indemnitee from the right, or
otherwise affect in any manner any right of Indemnitee, to receive payments of Indemnifiable
Amounts or advancements of Indemnifiable Expenses unless the Company’s ability to defend in such
Proceeding is materially and adversely prejudiced thereby.

          (b) Defense by Company. Subject to the provisions of the last sentence of this
Section 10(b), the Company shall have the right to defend Indemnitee in any Proceeding which may
give rise to the payment of Indemnifiable Amounts hereunder; provided, however that
the Company shall notify Indemnitees of any such decision to defend within ten (10) calendar days
of receipt of notice of any such Proceeding under Section 10(a) above. The Company shall not,
without the prior written consent of Indemnitees, consent to the entry of any judgment against any
Indemnitee or enter into any settlement or compromise which (i) includes an admission of fault of
any Indemnitee or (ii) does not include, as an unconditional term thereof, the full release of any
Indemnitee from all liability in respect of such Proceeding, which release shall be in form and
substance reasonably satisfactory to Indemnitees. This Section 10(b) shall not apply to a
Proceeding brought by any Indemnitee under Section 9(a) above or pursuant to Section 17 below.

          (c) Indemnitee’s Right to Counsel. Notwithstanding the foregoing and the provisions
of Section 10(b) above, if in a Proceeding to which any Indemnitee is a party by reason of such
Indemnitee’s Corporate Status, (i) Indemnitee reasonably concludes that Indemnitee may have
separate defenses or counterclaims to assert with respect to any issue which may not be consistent
with the position of other defendants in such Proceeding, (ii) a conflict of interest exists
between Indemnitee and the Company, or (iii) if the Company fails to assume the defense of such
proceeding in a timely manner, Indemnitee shall be entitled to be represented by separate legal
counsel of Indemnitee’s choice at the expense of the Company. In addition, if the Company fails to
comply with any of its obligations under this Agreement or in the event that the Company takes any
action to declare this Agreement void or unenforceable, or institutes any action, suit or
proceeding to deny or to recover from Indemnitee the benefits intended to be provided to Indemnitee
hereunder, Indemnitee shall have the right to retain counsel of Indemnitee’s choice, at the expense
of the Company, to represent Indemnitee in connection with any such matter.

     11. Representations and Warranties of the Company. The Company hereby represents and
warrants to Indemnitees as follows:

          (a) Authority. The Company has all necessary power and authority to enter into, and
be bound by the terms of, this Agreement, and the execution, delivery and performance of the
undertakings contemplated by this Agreement have been duly authorized by the Company.

          (b) Enforceability. This Agreement, when executed and delivered by the Company in
accordance with the provisions hereof, shall be a legal, valid and binding obligation of the
Company, enforceable against the Company in accordance with its terms, except as such
enforceability may be limited by applicable bankruptcy, insolvency, moratorium, reorganization or
similar laws affecting the enforcement of creditors’ rights generally.

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     12. Contract Rights Not Exclusive. The rights to payment of Indemnifiable Amounts and
advancement of Indemnifiable Expenses provided by this Agreement shall be in addition to, but not
exclusive of, any other rights which any Indemnitee may have at any time under applicable law, the
Company’s Certificate of Incorporation, Bylaws, or any other agreement, vote of stockholders or
directors (or a committee of directors), or otherwise, both as to action in TrustWave Directors’
official capacities and as to action in any other capacities as a result of TrustWave Directors’
serving as directors of the Company.

     13. Successors. This Agreement shall be (a) binding upon all successors and assigns
of the Company (including any transferee of all or a substantial portion of the business, stock
and/or assets of the Company and any direct or indirect successor by merger or consolidation or
otherwise by operation of law) and (b) binding on and shall inure to the benefit of the legal or
personal representatives, heirs, executors and administrators of Indemnitees. This Agreement shall
continue for the benefit of each Indemnitee and such legal or personal representative, heir,
executor and administrator after such Indemnitee has ceased to have Corporate Status.

     14. Subrogation. In the event of any payment of Indemnifiable Amounts under this
Agreement, the Company shall be subrogated to the extent of such payment to all of the rights of
contribution or recovery of Indemnitees against other persons, and Indemnitees shall take, at the
request of the Company, all reasonable action necessary to secure such rights, including the
execution of such documents as are necessary to enable the Company to bring suit to enforce such
rights.

     15. Change in Law. To the extent that a change in Delaware law (whether by statute or
judicial decision) shall permit broader indemnification or advancement of expenses than is provided
under the terms of this Agreement, Indemnitees, including the TrustWave Directors, shall be
entitled to such broader indemnification and advancements, and this Agreement shall be deemed to be
amended to such extent.

     16. Severability. Whenever possible, each provision of this Agreement shall be
interpreted in such a manner as to be effective and valid under applicable law, but if any
provision of this Agreement, or any clause thereof, shall be determined by a court of competent
jurisdiction to be illegal, invalid or unenforceable, in whole or in part, such provision or clause
shall be limited or modified in its application to the minimum extent necessary to make such
provision or clause valid, legal and enforceable, and the remaining provisions and clauses of this
Agreement shall remain fully enforceable and binding on the parties.

     17. Indemnitee as Plaintiff. Except as provided in the next sentence, Indemnitees
shall not be entitled to payment of Indemnifiable Amounts or advancement of Indemnifiable Expenses
with respect to a Proceeding brought by any Indemnitee against the Company, any Entity which it
controls, any director or officer thereof, or any third party, unless the Board of Directors of the
Company has consented to the initiation of such Proceeding. This Section shall not apply to
affirmative defenses asserted by Indemnitee in an action brought against Indemnitee.

     18. Modifications and Waiver. Except as provided in Section 15 above with respect to
changes in Delaware law which broaden the right of Indemnitees to be indemnified by the Company, no
supplement, modification or amendment of this Agreement shall be binding unless

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executed in writing by each of the parties hereto. No waiver of any of the provisions of this
Agreement shall be deemed or shall constitute a waiver of any other provisions of this Agreement
(whether or not similar), nor shall such waiver constitute a continuing waiver.

     19. General Notices. All notices, requests, demands and other communications
hereunder shall be in writing and shall be deemed to have been duly given (a) when delivered by
hand, (b) when transmitted by facsimile and receipt is acknowledged, or (c) if mailed by certified
or registered mail with postage prepaid, on the third business day after the date on which it is so
mailed:

If to Indemnitees, to:

c/o TrustWave Corporation

201 Defense Highway, Suite 205

Annapolis, MD 21401

Facsimile: 410.571.8493

Attention: General Counsel

If to the Company, to:

TrustWave Holdings, Inc.

c/o TrustWave Corporation

201 Defense Highway, Suite 205

Annapolis, MD 21401

Facsimile: 410.571.8493

Attention: General Counsel

or to such other address as may have been furnished in the same manner by any party to the others.

     20. Governing Law; Consent to Jurisdiction; Service of Process. This Agreement shall
be governed by and construed in accordance with the laws of the State of Delaware without regard to
its rules of conflict of laws. Each of the Company and Indemnitees hereby irrevocably and
unconditionally consents to submit to the exclusive jurisdiction of the state and federal courts of
the State of Delaware, (the “Delaware Courts”) for any litigation arising out of or
relating to this Agreement and the transactions contemplated hereby (and agrees not to commence any
litigation relating thereto except in such courts), waives any objection to the laying of venue of
any such litigation in the Delaware Court and agrees not to plead or claim in any Delaware Court
that such litigation brought therein has been brought in an inconvenient forum. Each of the
parties hereto agrees, (a) to the extent such party is not otherwise subject to service of process
in the State of Delaware, to appoint and maintain an agent in the State of Delaware as such party’s
agent for acceptance of legal process, and (b) that service of process may also be made on such
party by prepaid certified mail with a proof of mailing receipt validated by the United States
Postal Service constituting evidence of valid service. Service made pursuant to (a) or (b) above
shall have the same legal force and effect as if served upon such party personally within the State
of Delaware. For purposes of implementing the parties’ agreement to appoint and maintain an agent
for service of process in the State of Delaware, each such party does hereby appoint the Company’s
registered agent as such agent and each such party hereby agrees to complete all actions necessary
for such appointment.

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     21. Counterparts. This Agreement may be executed by facsimile and in one or more
counterparts, each of which will be deemed to be an original, but all of which will be one and the
same document.

* * * Remainder of Page Intentionally Left Blank; Signature Page Follows * * *

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     IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the day and year
first above written.

	 	 	 	 	 
	 	COMPANY:

TRUSTWAVE HOLDINGS, INC.

 	 
	 	By:  	/s/
Phillip J. Smith 	 
	 	 	Name:  	Phillip J. Smith 	 
	 	 	Title:  	General Counsel 	 
	 
	 	INDEMNITEES:

 	 
	 	/s/ Joseph Patanella
 	 
	 	Joseph Patanella 	 
	 	 	 
	 	                                              /s/ Erik Schetina
 	 
	 	Erik Schetina 	 
	 	 	 

SIGNATURE PAGE TO

INDEMNIFICATION AGREEMENTexv10w39

Exhibit 10.39

INDEMNIFICATION AGREEMENT

     THIS INDEMNIFICATION AGREEMENT is made and entered into as of March 14, 2005 (this
“Agreement”), by and between TRUSTWAVE HOLDINGS, INC., a Delaware corporation (the
“Company,” which term shall include, where appropriate, any Entity (as hereinafter defined)
controlled directly or indirectly by the Company), Financial Technology Management II, LLC
(“FTV”), Richard Garman and Kevin Bradford (including any successor nominees nominated by
FTV, the “FTV Directors”) (FTV, FTV Affiliates (as hereinafter defined) and the FTV
Directors are sometimes referred to herein collectively as “Indemnitees,” and individually
as “Indemnitee”):

     WHEREAS, the Company is a party to that certain Contribution Agreement, dated as of the date
hereof, by and among the Company, certain affiliates of FTV and other investors (the
“Contribution Agreement”);

     WHEREAS, pursuant to the Stockholders Agreement (as defined in the Contribution Agreement),
two (2) directors of the Company shall be nominated by FTV;

     WHEREAS, as a condition to the Contribution Agreement, the Company is required to enter into
this Agreement with Indemnitees;

     WHEREAS, increased corporate litigation has subjected directors and their affiliates to
litigation risks and expenses, and the limitations on the availability of directors and officers
liability insurance have made it increasingly difficult for the Company to attract and retain such
persons;

     WHEREAS, the Company’s Certificate of Incorporation (as the same may be amended and restated
from time to time) requires it to indemnify its directors to the fullest extent permitted by the
Delaware General Corporation Law and permit it to make other indemnification arrangements and
agreements;

     WHEREAS, the Company desires to provide Indemnitees with specific contractual assurance of
Indemnitees’ rights to full indemnification against litigation risks and expenses (regardless,
among other things, of any amendment to or revocation of the Company’s Certificate of Incorporation
and Bylaws, or any change in the composition of its Board of Directors);

     WHEREAS, the Company intends that this Agreement provide Indemnitees with greater protection
than that which is provided by the Company’s Certificate of Incorporation; and

     WHEREAS, the parties desire to memorialize their agreement regarding Indemnitees’ rights and
to specifically include FTV and the FTV Affiliates as Indemnitees.

 

 

     NOW, THEREFORE, in consideration of the promises and the covenants contained herein, the
Company and Indemnitees do hereby covenant and agree as follows:

     1. Definitions.

          (a) “Corporate Status” describes the status of (A) an Entity (including its
affiliates) which is nominating or has nominated a director of the Company or (B) a person who is
serving or has served (i) as a director of the Company, (ii) in any capacity with respect to any
employee benefit plan of the Company, or (iii) as a director, partner, trustee, officer, employee
or agent of any other Entity at the request of the Company. For purposes of subsection (iii) of
this Section 1(a), if Indemnitee is serving or has served as a director, partner, trustee, officer,
employee or agent of a Subsidiary, Indemnitee shall be deemed to be serving at the request of the
Company.

          (b) “Entity” shall mean any corporation, partnership, limited liability company, joint
venture, trust, foundation, association, organization or other legal entity.

          (c) “Expenses” shall mean all fees, costs and expenses reasonably incurred by
Indemnitee in connection with any Proceeding (as defined below), including, without limitation,
attorneys’ fees, disbursements and retainers (including, without limitation, any such fees,
disbursements and retainers incurred by Indemnitee pursuant to Sections 9 and 10(c) of this
Agreement), fees and disbursements of expert witnesses and professional advisors (including,
without limitation, accountants), court costs, transcript costs, duplicating, printing and binding
costs, telephone and fax transmission charges, postage, delivery services, and other disbursements
and expenses.

          (d) “FTV Affiliates” shall mean all employees, managers and members of FTV and all
entities controlled by FTV including without limitation Financial Technology Ventures II, L.P. and
Financial Technology Ventures II (Q), L.P.

          (e) “Indemnifiable Expenses,” “Indemnifiable Liabilities” and
“Indemnifiable Amounts” shall have the meanings ascribed to those terms in Section 3(a)
below.

          (f) “Liabilities” shall mean judgments, damages, liabilities, losses, penalties,
excise taxes, fines and amounts paid in settlement.

          (g) “Proceeding” shall mean any threatened, pending or completed claim, action, suit,
arbitration, alternate dispute resolution process, investigation, administrative hearing, appeal,
or any other proceeding, whether civil, criminal, administrative, arbitrative or investigative,
whether formal or informal, including a proceeding initiated by any Indemnitee pursuant to Section
9 of this Agreement to enforce Indemnitees’ rights hereunder.

          (h) “Subsidiary” shall mean any corporation, partnership, limited liability company,
joint venture, trust or other Entity of which the Company owns (either directly or through or
together with another Subsidiary of the Company) either (i) a general partner, managing member or
other similar interest or (ii) (A) 50% or more of the voting power of the voting capital equity
interests of such corporation, partnership, limited liability company, joint venture or other
Entity, or (B) 50% or more of the outstanding voting capital stock or other

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voting equity interests of such corporation, partnership, limited liability company, joint
venture or other Entity.

     2. Services of Indemnitees. In consideration of the Company’s covenants and
commitments hereunder, the FTV Directors shall serve as, or continue to serve as, directors of the
Company. However, this Agreement shall not impose any obligation on Indemnitees or the Company to
continue the FTV Directors’ service to the Company beyond any period otherwise required by law or
by other agreements or commitments of the parties, if any.

     3. Agreement to Indemnify. The Company agrees to indemnify each Indemnitee as
follows:

          (a) Proceedings Other Than By or In the Right of the Company. Subject to the
exceptions contained in Section 4(a) below, if Indemnitee was or is a party or is threatened to be
made a party to any Proceeding (other than an action by or in the right of the Company) by reason
of Indemnitee’s Corporate Status, Indemnitee shall be indemnified by the Company against all
Expenses and Liabilities incurred or paid by Indemnitee in connection with such Proceeding
(referred to herein as “Indemnifiable Expenses” and “Indemnifiable Liabilities,”
respectively, and collectively as “Indemnifiable Amounts”).

          (b) Proceedings By or In the Right of the Company. Subject to the exceptions
contained in Section 4(b) below, if Indemnitee was or is a party or is threatened to be made a
party to any Proceeding by or in the right of the Company by reason of Indemnitee’s Corporate
Status, Indemnitee shall be indemnified by the Company against all Indemnifiable Expenses.

          (c) Conclusive Presumption Regarding Standard of Care. In making any determination
required to be made under Delaware law or other law with respect to entitlement to indemnification
hereunder, the person, persons or entity making such determination shall presume that Indemnitee is
entitled to indemnification under this Agreement if Indemnitee submitted a request therefor in
accordance with Section 5 of this Agreement, and the Company shall have the burden of proof to
overcome that presumption in connection with the making by any person, persons or entity of any
determination contrary to that presumption.

     4. Exceptions to Indemnification. Each Indemnitee shall be entitled to
indemnification under Sections 3(a) and 3(b) above in all circumstances other than with respect to
any specific claim, issue or matter involved in the Proceeding out of which Indemnitee’s claim for
indemnification has arisen, as follows:

          (a) Proceedings Other Than By or In the Right of the Company. If indemnification is
requested under Section 3(a) and it has been finally adjudicated by a court of competent
jurisdiction that, in connection with such specific claim, issue or matter, (A) Indemnitee failed
to act (i) in good faith and (ii) in a manner Indemnitee reasonably believed to be in or not
opposed to the best interests of the Company, or (B) with respect to any criminal action or
proceeding, Indemnitee had reasonable cause to believe that Indemnitee’s conduct was unlawful,
Indemnitee shall not be entitled to payment of Indemnifiable Amounts hereunder.

          (b) Proceedings By or In the Right of the Company. If indemnification is requested
under Section 3(b) and

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               (i) it has been finally adjudicated by a court of competent jurisdiction that, in connection
with such specific claim, issue or matter, Indemnitee failed to act (A) in good faith and (B) in a
manner Indemnitee reasonably believed to be in or not opposed to the best interests of the Company,
Indemnitee shall not be entitled to payment of Indemnifiable Expenses hereunder; or

               (ii) it has been finally adjudicated by a court of competent jurisdiction that Indemnitee is
liable to the Company with respect to such specific claim, no Indemnifiable Expenses shall be paid
with respect to such claim, issue or matter unless a court of competent jurisdiction in which such
Proceeding was brought shall determine upon application that, despite the adjudication of
liability, but in view of all the circumstances of the case, Indemnitee is fairly and reasonably
entitled to indemnification for such Indemnifiable Expenses which such court shall deem proper; or

               (iii) it has been finally adjudicated by a court of competent jurisdiction that Indemnitee is
liable to the Company for an accounting of profits made from the purchase or sale by the Indemnitee
of securities of the Company pursuant to the provisions of Section 16(b) of the Securities Exchange
Act of 1934, the rules and regulations promulgated thereunder and amendments thereto or similar
provisions of any federal, state or local statutory law.

          (c) Insurance Proceeds. To the extent payment is actually made to Indemnitee under a
valid and collectible insurance policy in respect of Indemnifiable Expenses in connection with such
specific claim, issue or matter, Indemnitee shall not be entitled to payment of Indemnifiable
Expenses hereunder except in respect of any excess Indemnifiable Expenses beyond the amount of
payment under such insurance.

     5. Procedure for Payment of Indemnifiable Amounts. Indemnitee shall submit to the
Company a written request specifying the Indemnifiable Amounts for which Indemnitee seeks payment
under Section 3 of this Agreement and the basis for the claim. The Company shall pay such
Indemnifiable Amounts to Indemnitee within sixty (60) calendar days of receipt of the request. At
the request of the Company, Indemnitee shall furnish such documentation and information within
Indemnitee’s control or possession or as is reasonably available to Indemnitee, and necessary to
establish that Indemnitee is entitled to indemnification hereunder.

     6. Indemnification for Expenses of a Party Who is Wholly or Partly Successful.
Notwithstanding any other provision of this Agreement, to the extent that Indemnitee is, by reason
of his Corporate Status, a party to and is successful, on the merits or otherwise, in any
Proceeding, he shall be indemnified to the maximum extent permitted by law, as such may be amended
from time to time, against all Expenses actually and reasonably incurred by him or on his behalf in
connection therewith. If Indemnitee is not wholly successful in such Proceeding but is successful,
on the merits or otherwise, as to one or more but less than all claims, issues or matters in such
Proceeding, the Company shall indemnify Indemnitee against all Expenses actually and reasonably
incurred by him or on his behalf in connection with each successfully resolved claim, issue or
matter. For purposes of this Section and without limitation, the termination of any claim, issue
or matter in such a Proceeding by dismissal, with or without prejudice, shall be deemed to be a
successful result as to such claim, issue or matter.

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     7. Effect of Certain Resolutions. Neither the settlement or termination of any
Proceeding nor the failure of the Company to award indemnification or to determine that
indemnification is payable shall create a presumption that an Indemnitee is not entitled to
indemnification hereunder. In addition, the termination of any Proceeding against the Company (and
not the Indemnitee) by judgment, order, settlement, conviction, or upon a plea of nolo contendere
or its equivalent shall not create a presumption that such Indemnitee did not act in good faith and
in a manner which Indemnitee reasonably believed to be in or not opposed to the best interests of
the Company or, with respect to any criminal action or proceeding, had reasonable cause to believe
that such Indemnitee’s action was unlawful.

     8. Agreement to Advance Expenses; Undertaking. The Company shall advance all Expenses
incurred by or on behalf of Indemnitee in connection with any Proceeding, including a Proceeding by
or in the right of the Company, in which Indemnitee is involved by reason of such Indemnitee’s
Corporate Status within ten (10) calendar days after the receipt by the Company of a written
statement from Indemnitee requesting such advance or advances from time to time, whether prior to
or after final disposition of such Proceeding, upon receipt of an undertaking by Indemnitee to
repay any and all of the amount of Indemnifiable Expenses paid to Indemnitee if it is finally
determined by a court of competent jurisdiction that Indemnitee is not entitled under this
Agreement to indemnification with respect to such Expenses. Such written statement shall specify
the Indemnifiable Expenses for which Indemnitee seeks an advancement under this Agreement, together
with documentation evidencing that Indemnitee has incurred such Indemnifiable Expenses. This
undertaking is an unlimited general obligation of each of Indemnitees.

     9. Remedies of Indemnitee.

          (a) Right to Petition Court. In the event that any Indemnitee makes a request for
payment of Indemnifiable Amounts under Sections 3 and 5 above or a request for an advancement of
Indemnifiable Expenses under Section 8 above and the Company fails to make such payment or
advancement in a timely manner pursuant to the terms of this Agreement, such Indemnitee may
petition the court of competent jurisdiction to enforce the Company’s obligations under this
Agreement.

          (b) Burden of Proof. In any judicial proceeding brought under Section 9(a) above, the
Company shall have the burden of proving that Indemnitee is not entitled to payment of
Indemnifiable Amounts hereunder.

          (c) Expenses. The Company agrees to reimburse Indemnitee in full for any Expenses
incurred by Indemnitee in connection with any action brought by Indemnitee under Section 9(a)
above, or in connection with any claim or counterclaim brought by the Company in connection
therewith, but only in the event that Indemnitee is successful on the merits in connection with any
such action.

          (d) Failure to Act Not a Defense. The failure of the Company (including its Board of
Directors or any committee thereof, independent legal counsel, or stockholders) to make a
determination concerning the permissibility of the payment of Indemnifiable Amounts or the
advancement of Indemnifiable Expenses under this Agreement shall not be a defense in any

- 5 -

 

action brought under Section 9(a) above, and shall not create a presumption that such payment
or advancement is not permissible.

     10. Defense of the Underlying Proceeding.

          (a) Notice by Indemnitee. Indemnitees agree to notify the Company promptly upon being
served with any summons, citation, subpoena, complaint, indictment, information, or other document
relating to any Proceeding which may result in the payment of Indemnifiable Amounts or the
advancement of Indemnifiable Expenses hereunder; provided, however, that the
failure to give any such notice shall not disqualify any Indemnitee from the right, or otherwise
affect in any manner any right of Indemnitee, to receive payments of Indemnifiable Amounts or
advancements of Indemnifiable Expenses unless the Company’s ability to defend in such Proceeding is
materially and adversely prejudiced thereby.

          (b) Defense by Company. Subject to the provisions of the last sentence of this
Section 10(b), the Company shall have the right to defend Indemnitee in any Proceeding which may
give rise to the payment of Indemnifiable Amounts hereunder; provided, however that
the Company shall notify Indemnitees of any such decision to defend within ten (10) calendar days
of receipt of notice of any such Proceeding under Section 10(a) above. The Company shall not,
without the prior written consent of Indemnitees, consent to the entry of any judgment against any
Indemnitee or enter into any settlement or compromise which (i) includes an admission of fault of
any Indemnitee or (ii) does not include, as an unconditional term thereof, the full release of any
Indemnitee from all liability in respect of such Proceeding, which release shall be in form and
substance reasonably satisfactory to Indemnitees. This Section 10(b) shall not apply to a
Proceeding brought by any Indemnitee under Section 9(a) above or pursuant to Section 17 below.

          (c) Indemnitee’s Right to Counsel. Notwithstanding the foregoing and the provisions
of Section 10(b) above, if in a Proceeding to which any Indemnitee is a party by reason of such
Indemnitee’s Corporate Status, (i) Indemnitee reasonably concludes that Indemnitee may have
separate defenses or counterclaims to assert with respect to any issue which may not be consistent
with the position of other defendants in such Proceeding, (ii) a conflict of interest exists
between Indemnitee and the Company, or (iii) if the Company fails to assume the defense of such
proceeding in a timely manner, Indemnitee shall be entitled to be represented by separate legal
counsel of Indemnitee’s choice at the expense of the Company. In addition, if the Company fails to
comply with any of its obligations under this Agreement or in the event that the Company takes any
action to declare this Agreement void or unenforceable, or institutes any action, suit or
proceeding to deny or to recover from Indemnitee the benefits intended to be provided to Indemnitee
hereunder, Indemnitee shall have the right to retain counsel of Indemnitee’s choice, at the expense
of the Company, to represent Indemnitee in connection with any such matter.

     11. Representations and Warranties of the Company. The Company hereby represents and
warrants to Indemnitees as follows:

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          (a) Authority. The Company has all necessary power and authority to enter into, and
be bound by the terms of, this Agreement, and the execution, delivery and performance of the
undertakings contemplated by this Agreement have been duly authorized by the Company.

          (b) Enforceability. This Agreement, when executed and delivered by the Company in
accordance with the provisions hereof, shall be a legal, valid and binding obligation of the
Company, enforceable against the Company in accordance with its terms, except as such
enforceability may be limited by applicable bankruptcy, insolvency, moratorium, reorganization or
similar laws affecting the enforcement of creditors’ rights generally.

     12. Contract Rights Not Exclusive. The rights to payment of Indemnifiable Amounts and
advancement of Indemnifiable Expenses provided by this Agreement shall be in addition to, but not
exclusive of, any other rights which any Indemnitee may have at any time under applicable law, the
Company’s Certificate of Incorporation, Bylaws, or any other agreement, vote of stockholders or
directors (or a committee of directors), or otherwise, both as to action in FTV Directors’ official
capacities and as to action in any other capacities as a result of FTV Directors’ serving as
directors of the Company.

     13. Successors. This Agreement shall be (a) binding upon all successors and assigns
of the Company (including any transferee of all or a substantial portion of the business, stock
and/or assets of the Company and any direct or indirect successor by merger or consolidation or
otherwise by operation of law) and (b) binding on and shall inure to the benefit of the legal or
personal representatives, heirs, executors and administrators of Indemnitees. This Agreement shall
continue for the benefit of each Indemnitee and such legal or personal representative, heir,
executor and administrator after such Indemnitee has ceased to have Corporate Status.

     14. Subrogation. In the event of any payment of Indemnifiable Amounts under this
Agreement, the Company shall be subrogated to the extent of such payment to all of the rights of
contribution or recovery of Indemnitees against other persons, and Indemnitees shall take, at the
request of the Company, all reasonable action necessary to secure such rights, including the
execution of such documents as are necessary to enable the Company to bring suit to enforce such
rights.

     15. Change in Law. To the extent that a change in Delaware law (whether by statute or
judicial decision) shall permit broader indemnification or advancement of expenses than is provided
under the terms of this Agreement, Indemnitees, including the FTV Directors, shall be entitled to
such broader indemnification and advancements, and this Agreement shall be deemed to be amended to
such extent.

     16. Severability. Whenever possible, each provision of this Agreement shall be
interpreted in such a manner as to be effective and valid under applicable law, but if any
provision of this Agreement, or any clause thereof, shall be determined by a court of competent
jurisdiction to be illegal, invalid or unenforceable, in whole or in part, such provision or clause
shall be limited or modified in its application to the minimum extent necessary to make such
provision or clause valid, legal and enforceable, and the remaining provisions and clauses of this
Agreement shall remain fully enforceable and binding on the parties.

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     17. Indemnitee as Plaintiff. Except as provided in the next sentence, Indemnitees
shall not be entitled to payment of Indemnifiable Amounts or advancement of Indemnifiable Expenses
with respect to a Proceeding brought by any Indemnitee against the Company, any Entity which it
controls, any director or officer thereof, or any third party, unless the Board of Directors of the
Company has consented to the initiation of such Proceeding. This Section shall not apply to
affirmative defenses asserted by Indemnitee in an action brought against Indemnitee.

     18. Modifications and Waiver. Except as provided in Section 15 above with respect to
changes in Delaware law which broaden the right of Indemnitees to be indemnified by the Company, no
supplement, modification or amendment of this Agreement shall be binding unless executed in writing
by each of the parties hereto. No waiver of any of the provisions of this Agreement shall be
deemed or shall constitute a waiver of any other provisions of this Agreement (whether or not
similar), nor shall such waiver constitute a continuing waiver.

     19. General Notices. All notices, requests, demands and other communications
hereunder shall be in writing and shall be deemed to have been duly given (a) when delivered by
hand, (b) when transmitted by facsimile and receipt is acknowledged, or (c) if mailed by certified
or registered mail with postage prepaid, on the third business day after the date on which it is so
mailed:

If to Indemnitee, to:

Financial Technology Management II, LLC

601 California Street, Suite 2200

San Francisco, California 94108

Facsimile: 415.229.3005

Attention: David Haynes

If to the Company, to:

TrustWave Holdings, Inc.

c/o TrustWave Corporation

201 Defense Highway, Suite 205

Annapolis, MD 21401

Facsimile: 410.571.8493

Attention: General Counsel

or to such other address as may have been furnished in the same manner by any party to the others.

     20. Governing Law; Consent to Jurisdiction; Service of Process. This Agreement shall
be governed by and construed in accordance with the laws of the State of Delaware without regard to
its rules of conflict of laws. Each of the Company and Indemnitees hereby irrevocably and
unconditionally consents to submit to the exclusive jurisdiction of the state and federal courts of
the State of Delaware, (the “Delaware Courts”) for any litigation arising out of or
relating to this Agreement and the transactions contemplated hereby (and agrees not to commence any
litigation relating thereto except in such courts), waives any objection to the laying of venue of
any such litigation in the Delaware Court and agrees not to plead or claim in any Delaware Court
that such litigation brought therein has been brought in an inconvenient

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forum. Each of the parties hereto agrees, (a) to the extent such party is not otherwise
subject to service of process in the State of Delaware, to appoint and maintain an agent in the
State of Delaware as such party’s agent for acceptance of legal process, and (b) that service of
process may also be made on such party by prepaid certified mail with a proof of mailing receipt
validated by the United States Postal Service constituting evidence of valid service. Service made
pursuant to (a) or (b) above shall have the same legal force and effect as if served upon such
party personally within the State of Delaware. For purposes of implementing the parties’ agreement
to appoint and maintain an agent for service of process in the State of Delaware, each such party
does hereby appoint the Company’s registered agent as such agent and each such party hereby agrees
to complete all actions necessary for such appointment.

     21. Counterparts. This Agreement may be executed by facsimile and in one or more
counterparts, each of which will be deemed to be an original, but all of which will be one and the
same document.

* * * Remainder of Page Intentionally Left Blank; Signature Page Follows * * *

- 9 -

 

     IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the day and year
first above written.

	 	 	 	 	 
	 	COMPANY:

TRUSTWAVE HOLDINGS, INC.

 	 
	 	By:  	/s/
Joseph Patanella 	 
	 	 	Name:  	Joseph Patanella 	 
	 	 	Title:  	Chief Executive Officer 	 
	 
	 	INDEMNITEES:

By: Financial Technology Management II, LLC
 
	 
	 	By:  	/s/
Richard Garman 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 

	 	 	 	 	 
	 	                                              /s/ Richard Garman
 	 
	 	Richard Garman 	 

	 	 	 	 	 
	 	                                              /s/ Kevin Bradford
 	 
	 	Kevin Bradford 	 
	 	 	 

SIGNATURE PAGE TO

INDEMNIFICATION AGREEMENT

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