SECOND AMENDMENT TO STOCKHOLDERS’ AGREEMENT

Exhibit 10.21

SECOND AMENDMENT TO STOCKHOLDERS’ AGREEMENT

     THIS SECOND AMENDMENT TO STOCKHOLDERS’ AGREEMENT (this “Amendment”) is entered into as of June 3, 2008 (the “Amendment Date”), by and among TrustWave Holdings, Inc., a Delaware corporation (the “Company”), and the persons signatory hereto (the “Signatories”).

RECITALS

     WHEREAS, the Company and its stockholders are parties to that certain Stockholders’ Agreement, dated as of March 14, 2005, as amended through the date hereof (as so amended, the “Original Agreement”); and

     WHEREAS, all capitalized terms used in this Amendment which are not defined herein shall have the respective meanings assigned to them in the Original Agreement; and

     WHEREAS, the Signatories constitute the holders of at least a majority of the issued and outstanding shares of Common Stock (on an as-converted basis); and

     WHEREAS, the parties hereto desire to amend the Original Agreement as provided in this Amendment.

     NOW, THEREFORE, in consideration of the foregoing recitals and the mutual promises, representations, warranties, covenants and conditions contained in this Amendment and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereto, intending to be legally bound, agree as follows:

     1. Exhibit C. Exhibit C attached to the Original Agreement is hereby amended to read, in its entirety, as set forth on Exhibit C attached to this Amendment.

     2. No Other Amendments. Except as expressly amended by this Amendment, all of the terms and provisions of the Original Agreement shall remain in full force and effect.

     3. Counterparts. This Amendment may be executed by facsimile and in counterparts, each of which shall be an original, but all of which together shall constitute one instrument.

[Signature Page Follows]

     IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be executed as of the Amendment Date.

	COMPANY: TRUSTWAVE HOLDINGS, INC.
	By:	/s/ Xxxxxx XxXxxxxx
		Name:	Xxxxxx XxXxxxxx
		Title:	Chief Executive Officer

	STOCKHOLDERS: Financial Technology Ventures II (Q), L.P.
	By:	Financial Technology Management, II, LLC

	By:	/s/ Xxxxxxx Xxxxxx
		Name:	Xxxxxxx Xxxxxx
		Title:

	Financial Technology Ventures II, L.P.
	By:	Financial Technology Management, II, LLC

	By:	/s/ Xxxxxxx Xxxxxx
		Name:
		Title:

/s/ Xxxxxxx Xxxxxxx  

Xxxxxxx Xxxxxxx 

/s/ Xxxxx Xxxxxxxxx  

Xxxxx Xxxxxxxxx 

2

	DBRC Investments, LLC.
	By:	/s/
		Name:
		Title:

/s/ Xxxxxx Xxxxxxxxx  

Xxxxxx X. Xxxxxxxxx 

/s/ Xxxxxxx X. Xxxxx  

Xxxxxxx X. Xxxxx 

	Caledonia Investments, L.P.
	By:	/s/ Xxx Xxxxxxxxx
		Name:	Xxx Xxxxxxxxx
		Title:

	The Xxxxxxxxx Family Limited Partnership
	By:	/s/ Xxx Xxxxxxxxx
		Name:	Xxx Xxxxxxxxx
		Title:

	MBK Ventures, LLC
	By:	/s/ Xxxxxx XxXxxxxx
		Name:	Xxxxxx XxXxxxxx
		Title:	Manager

Xxxx Xxxxxxxx 

3

		THE PRODUCTIVITY FUND, IV L.P.
		By:		First Analysis Management Company IV, L.L.C., its General Partner
		By:		First Analysis Venture Operations and Research, L.L.C., its Member
		By:		First Analysis Corporation, its Manager

	By:	/s/ Xxxxxx X. Xxxxx
		Xxxxxx X. Xxxxx, Managing Director

		THE PRODUCTIVITY FUND, IV ADVISORS FUND, L.P.
		By:		First Analysis Management Company IV, L.L.C., its General Partner
		By:		First Analysis Venture Operations and Research, L.L.C., its Member
		By:		First Analysis Corporation, its Manager

	By:	/s/ Xxxxxx X. Xxxxx
		Xxxxxx X. Xxxxx, Managing Director

4

EXHIBIT C

List of Investors

Name and Address

Series A-1 Preferred
Financial Technology Ventures II (Q), L.P.
c/o Financial Technology Management II, LLC
000 Xxxxxxxxxx Xxxxxx, Xxxxx 0000
Xxx Xxxxxxxxx, Xxxxxxxxxx 00000
Attention: Xxxxx Xxxxxx
Facsimile: 415.229.3005

Financial Technology Ventures II, L.P.
c/o Financial Technology Management II, LLC
000 Xxxxxxxxxx Xxxxxx, Xxxxx 0000
Xxx Xxxxxxxxx, Xxxxxxxxxx 00000
Attention: Xxxxx Xxxxxx
Facsimile: 415.229.3005

Series A-2 Preferred
Xxxxx Xxxxx
000 Xxxxxxxx
Xxxxxxx, XX 00000

Xxxxxxx Xxxxxxx
c/o Xxxxxxx Xxxxx and Company
000 X. Xxxxx
Xxxxxxx, XX 00000

Xxxxxxx Xxxxxxx
c/o Xxxxxxx Xxxxx and Company
000 X. Xxxxx
Xxxxxxx, XX 00000

Xxxxx Xxxxxxxxx
000 Xxxxxxxx Xxxx
Xxxxxxxxxx, XX 00000

Series B Preferred
DBRC Investments, LLC.
00 Xxxx Xxxxxxx, Xxxxx 0000
Xxxxxxx, Xx 00000

Class A Common
Xxxxx Xxxxxxx Xxxxx
11816 Hunting Xxxxx Xxxxx
Xxxxxxx, Xxxxxxxx 00000

Xxxxx X. Xxxxxxxx
000 Xxxxxxxxxx Xxxx
Xxxxxxx, XX 00000

Caledonian Investments, L.P.
c/o Xxxxxxx X. Xxxxxxxxx
000 Xxxxxxx Xxxx
Xxxxxxxxx, XX 00000

The Xxxxxxxxx Family Limited Partnership
c/o Xxxxxxx X. Xxxxxxxxx
000 Xxxxxxx Xxxx
Xxxxxxxxx, XX 00000

Xxxxxx X. Xxxxxxxxx
0000 Xxxxxx Xxxxx Xxxx Xx
Xxxxxxxxx, Xxxxxxxx 00000

Xxxx X. Xxxxxxxx
00-00 Xxxxxx Xx
Xxx Xxxxxxx XX 00000

Xxxxxx Xxxxxxxxxx
0000 Xxxxxxxxxxxxx Xxx
Xxxxxxxxx, XX 00000

Xxxxxxx X. Xxxxx
00000 Xxxx Xxxxx Xxxx
Xxxxx, Xxxxxxxx 00000

Xxxxx Xxxxxxx
000 00^xx Xx
Xxxxxxxx, XX 00000

Xxxxxx Xxxxxxx
0000 Xxxxx Xxxxx Xx
Xxxx Xxxxxx, XX 00000

Xxxxx Xxxxxx
000 X 00^xx Xx #00
Xxx Xxxx, XX 00000

The Xxxxxxxxx Family Trust
c/o Xxxxx X. Xxxxxxxxx
000 Xxxxxx Xxxxxx Xxxxx
Xxxxxxxxxx, XX 00000

Xxxx Xxxxx
0000 Xxxx Xxxxxxxx Xxxxxxx
Xxxxxxxxx, XX 00000

MBK Ventures, LLC
000 Xxxx Xxxxx, Xxxxx 000
Xxxxxxx, Xxxxxxxx 00000
Attn: Xxxxxx Xxxxx and Xxxxxx XxXxxxxx, Managers

Productivity Fund IV, LP
Productivity Fund IV Advisors Fund, LP
FA Private Equity Fund IV, LP
FA Private Equity Fund IV GMBH
0 Xxxxx Xxxxxx Xxxxx 0000
Xxxxxxx, XX 00000

Prism Opportunity Fund SBIC, LP
000 X. Xxxxxxxx Xxx
Xxxxxxx, XX 00000

Argentum Capital Partners II, LP
00 Xxxxxxx Xxx
Xxx Xxxx, XX 00000

VM Funding, LLC
000 Xxxxxxx Xxxx
Xxxx XX 00000