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EXHIBIT 4.1

AMENDMENT NO. 2 TO SECOND AMENDED AND RESTATED

CREDIT AGREEMENT

     This Amendment No. 2 to Second Amended and Restated Credit Agreement (“Amendment”) dated as of
July 2, 2007 by and among the lenders signatories hereto (“Banks”), Comerica Bank as agent for the
Banks (in such capacity, “Agent”), and North Pointe Holdings Corporation, a Michigan corporation
(“Company”).

RECITALS

     A. Company and Banks entered into that certain Second Amended and Restated Credit Agreement
dated as of June 30, 2006, as previously amended (“Agreement”).

     B. The parties desire to further amend the Agreement.

     NOW, THEREFORE, the parties agree that the Agreement and the Term Notes are amended as
follows:

     1. The following definitions set forth in Section 1 of the Agreement are amended to read in
their entireties as follows:

     “Collateral Documents” shall mean the Guaranties, the Security Agreements, the
Pledge Agreements and all of the other acknowledgments, certificates, stock powers,
financing statements, instruments and other security documents executed by Company,
any Subsidiary or any other Person in favor of the Agent for the benefit of the
Banks and delivered to the Agent, as security for the Indebtedness, in each case as
of the date of execution of this Agreement or, from time to time, subsequent
thereto, in connection with the Guaranties, the Security Agreements, the Pledge
Agreements, this Agreement and the other Loan Documents, in each case, as such
collateral documents may be amended or otherwise modified from time to time.

     “Revolving Credit Aggregate Commitment” shall mean Thirty Five Million Dollars
($35,000,000) subject to reduction or termination under Section 2.13 or 8.2 hereof.

     “Revolving Credit Maturity Date” shall mean the earlier to occur of (i) July 1,
2010 (subject to extension as set forth in Section 2.16 of this Agreement), and (ii)
the date on which the Revolving Credit Aggregate Commitment shall be terminated
pursuant to Section 2.13 or Section 8.2 hereof.

     “Loan Documents” shall mean, collectively, this Agreement, the Notes, the
Guaranties, the Pledge Agreements, the Security Agreements, the Letter of

 

 

Credit Agreements, the Letters of Credit, any Interest Rate Protection
Agreements and any other documents, certificates, instruments or agreements executed
pursuant to or in connection with any such document or this Agreement, as such
documents may be amended from time to time.

     “Pledge Agreements” shall mean the Financial Pledge Agreement, the Company
Pledge Agreement, and the Capital City Pledge Agreement, as each may be amended from
time to time.

     “Security Agreement” shall mean the Second Amended and Restated Security
Agreement dated June 30, 2006 from certain of the Guarantors in favor of the Agent
for the benefit of the Banks, as amended from time to time; and/or the Security
Agreement dated July 2, 2007 from certain other Guarantors in favor of Agent for the
benefit of the Banks, as amended from time to time, and “Security Agreements” shall
mean both of them.

     2. The following definitions are added in alphabetical order to Section 1 of the Agreement to
read in their entireties as follows:

     “Acquisition” shall mean the acquisition by Capital City Acquisition Corp. of
one hundred percent (100%) of the capital stock of Targets pursuant to the
Acquisition Documents.

     “Acquisition Documents” shall mean the Stock Purchase Agreement and any other
related documents or agreements arising from or entered into pursuant to the terms
of the Stock Purchase Agreement.

     “Capital City Pledge Agreement” shall mean the Pledge Agreement (Capital City)
dated as of July 2, 2007 pursuant to which Capital City Acquisition Corp. grants to
Agent for the benefit of the Banks a first priority security interest in all of the
issued and outstanding Equity Interests of its Subsidiaries (other than the
Insurance Subsidiaries), as amended from time to time.

     “CCIC” shall mean Capital City Insurance Company, Inc., a South Carolina
corporation.

     “Stock Purchase Agreement” shall mean the Stock Purchase Agreement dated as of
May 11, 2007 by and among Company and Hinton G. Davis, HGD Investment Limited
Partnership, First Venture Holdings, LLC, Mary Teresa Davis Tanner, Hinton G. Davis
III, Grantor Trust, Susan Cheri Davis McMillan and Capital City Acquisition Corp.,
as amended.

     “Targets” shall mean Capital City Holding Company, Inc., Davis-Garvin Holdings,
Inc., Capital Excess & Surplus Brokers, Inc., Southeastern Claims Services, Inc.,
Safeco Products, Inc. and Charter Premium Audits, Inc., each a South Carolina
corporation, and “Target” shall mean any one of them.

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     3. The first sentence of Section 2.11 of the Agreement is amended to read in its entirety as
follows:

     “From the date hereof to (but excluding) the Revolving Credit Maturity Date,
the Company shall pay to each of the Revolving Credit Banks, a Revolving Credit
Facility Fee determined by multiplying one quarter of one percent (1/4%) per annum
times the average daily amount of the Revolving Credit Aggregate Commitment.”

     4. Section 2.13(i) of the Agreement is amended to read in its entirety as follows:

     “(i) each partial reduction of the Revolving Credit Aggregate Commitment shall
be in an aggregate amount equal to at least Five Million Dollars ($5,000,000) or a
larger integral multiple of One Million Dollars ($1,000,000);”

     5. Section 2.16 is added to the Agreement to read in its entirety as follows:

          “2.16 Extension of Revolving Credit Maturity Date.

     “(a) Provided that no Default or Event of Default has occurred and is
continuing, Company may, by written notice to Agent (with sufficient copies for each
Bank) (which notice shall be irrevocable and which shall not be deemed effective
unless actually received by Agent) prior to May 1 but not before April 1 of each
year beginning in 2010 (or at such other time as agreed to by the Agent and the
Majority Banks), request that each Bank extend the then applicable Revolving Credit
Maturity Date to a date that is one year later than the Revolving Credit Maturity
Date then in effect (each such request, a “Request”). Each Bank shall, not later
than 30 days after such Request, give written notice to the Agent stating whether
such Bank is willing to extend the Revolving Credit Maturity Date as requested. If
Agent has received the aforesaid written approvals of such Request from each of the
Banks, then, effective upon the date of Agent’s receipt of all such written
approvals from the Banks, the Revolving Credit Maturity Date shall be so extended
for such additional one year period, the term Revolving Credit Maturity Date shall
mean such extended date and Agent shall promptly notify the Company that such
extension has occurred.

     “(b) The Agent shall promptly notify the Company whether all of the Banks have
consented to such request. If the Agent does not so notify the Company within 30
days of the Agent’s receipt of such Request, the Agent shall be deemed to have
notified the Company that all of the Banks have not consented to the Company’s
request. If a Bank does not respond within 30 days after a Request it shall be
deemed to have denied the Request.

     “(c) Notwithstanding anything herein to the contrary, the Revolving Credit
Maturity Date will not be extended unless all Banks have consented to the
extension.”

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     6. Sections 6.16, 6.18 and 6.19 of the Agreement are amended to read in their entireties as
follows:

     “6.16 Maintain Risk-Based Capital. Not permit “total adjusted capital”
(within the meaning of the Risk-Based Capital for Insurers Model Act as promulgated
by the NAIC as of the Closing Date (the “Model Act”)) of any of its Insurance
Subsidiaries as of the last day of each fiscal year to be less than 275% of the
applicable “Authorized Control Level RBC” (within the meaning of the Model Act) for
such Insurance Subsidiary.

     “6.18 Net Premium and Gross Premium Ratio. Cause the Insurance
Subsidiaries to maintain as of the end of each fiscal year Net Premium Ratios and
Gross Premium Ratios of not more than the following amounts:

	 	 	 	 	 	 	 	 	 
	Insurance Subsidiary	 	Net Premium Ratio	 	Gross Premium Ratio
	NPCIC
	 	 	4.0 to 1.0	 	 	 	10.0 to 1.0	 
	HPIC
	 	 	4.0 to 1.0	 	 	 	10.0 to 1.0	 
	NPIC
	 	 	2.5 to 1.0	 	 	 	3.0 to 1.0	 
	CCIC
	 	 	2.5 to 1.0	 	 	 	3.0 to 1.0	 

     “6.19 Combined Ratio. Cause the Insurance Subsidiaries to maintain as
of the end of each fiscal year a Combined Ratio of not greater than 115%.”

     7. Section 8.1(m) of the Agreement is amended to read in its entirety as follows:

     “(m) if (i) the Best rating for NPIC, NPCIC, HPIC or CCIC is below the Required
Rating or (ii) Best shall withdraw its rating for any Insurance Subsidiary;”

     8. Schedules 5.6, 5.10, 5.16, 5.18 and 7.10 to the Agreement are amended to read in the form
of attached Schedules 5.6, 5.10, 5.16, 5.18 and 7.10.

     9. Company has informed Agent that the purchase price of the Acquisition will exceed Five
Million Dollars ($5,000,000). Agent and Banks consent to the Acquisition conditioned upon the
purchase price for the Acquisition not exceeding Forty One Million Dollars ($41,000,000).

     10. Company hereby represents and warrants that, after giving effect to the amendments and
consent contained herein, (a) execution, delivery and performance of this Amendment and any other
documents and instruments required under this Amendment or the Agreement are within Company’s
powers, have been duly authorized, are not in contravention of law or the terms of the Company’s
Articles of Incorporation or Bylaws and do not require the consent or approval of any governmental
body, agency, or authority; and this Amendment and any other documents and instruments required
under this Amendment or the Agreement, will be valid and binding in accordance with their terms;
(b) the representations and warranties of Company set forth in Sections 5.1 through 5.6 and 5.8
through 5.21 of the Agreement are true

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and correct in all material respects on and as of the date hereof with the same force and
effect as if made on and as of the date hereof; (c) the representations and warranties of Company
set forth in Section 5.7 of the Agreement are true and correct in all material respects as of the
date hereof with respect to the most recent financial statements furnished to the Bank by Company
in accordance with Section 6.1 of the Agreement; and (d) no Event of Default, or condition or event
which, with the giving of notice or the running of time, or both, would constitute an Event of
Default under the Agreement, has occurred and is continuing as of the date hereof.

     11. This Amendment shall be effective upon (a) execution hereof by Company, Agent and the
Banks, (b) execution by the existing Guarantors of a reaffirmation of Guaranty in the form of
attached Exhibit A, (c) execution and delivery by Company to Banks of Revolving Credit Notes in
form acceptable to Agent and each such Bank, (d) receipt by the Agent of evidence satisfactory to
Agent of the consummation of the Acquisition on the terms set forth in the Stock Purchase
Agreement, (e) execution and delivery by Company of an Assignment as Collateral Security in the
form of attached Exhibit K, (f) execution and delivery to Bank by each of the Sellers (as defined
in the Stock Purchase Agreement) of a Consent to Assignment as Collateral Security in the form
attached to the Assignment as Collateral Security, (g) execution and delivery by Capital City
Acquisition Corp., Capital Collection Services, Inc. and each Target and each of its Subsidiaries
of a Guaranty in the form of attached Exhibit L, (h) execution and delivery by Capital City
Acquisition Corp., Capital Collection Services, Inc. and each Target and each of its Subsidiaries
of a Security Agreement in the form of attached Exhibit M, (i) execution and delivery by North
Pointe Financial Services, Inc. of an Acknowledgment and Amendment to Pledge Agreement in the form
of attached Exhibit N, together with delivery of the original stock certificates evidencing North
Pointe Financial Services, Inc.’s ownership of 100% of Capital City Acquisition Corp. along with
stock assignments executed in blank, (j) execution and delivery by Capital City Acquisition Corp.
of a Stock Pledge Agreement in the form of attached Exhibit O, together with delivery of the
original stock certificates evidencing Capital City Acquisition Corp.’s ownership of 100% of each
of the Targets with stock assignments executed in blank, (k) receipt by the Agent of copies of the
executed Acquisition Documents, certified by a Responsible Officer as being true, correct and
complete which Acquisition Documents shall be in form and substance satisfactory to the Agent and
the Banks and each of the Acquisition Documents shall have been duly authorized, executed and
delivered by each of the parties thereto and shall be in full force and effect, (l) receipt by the
Agent of evidence satisfactory to Agent that all consents, authorizations and approvals of, and
filings and registrations with, and all other actions in respect of, any governmental authority or
other Person required in connection with the consummation of the transactions contemplated by the
Acquisition Documents shall have been obtained and shall be in full force and effect, and (m)
payment by Company to Agent, for the pro-rata benefit of the Banks, of a non-refundable amendment
fee in the amount of $24,500.

     12. This Amendment may be signed in any number of counterparts, each of which when so executed
and delivered shall be deemed an original, but all such counterparts together shall constitute but
one and the same instrument.

     13. Capitalized terms not defined herein shall have the meanings given to them in the
Agreement.

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     WITNESS the due execution hereof as of the day and year first above written.

	 	 	 	 	 	 	 	 	 
	COMERICA BANK, as Agent	 	 	 	NORTH POINTE HOLDINGS
CORPORATION
	 
	 	 	 	 	 	 	 	 
	By:

	 	 	 	 	 	By:	 	 
	 

	 	 
	 	 	 	 	 	 
	 

	 	Mark A. Rafdal
	 	 	 	 	 	James G. Petcoff
	 
	 	 	 	 	 	 	 	 
	Its:	 	Vice President	 	 	 	Its: Chairman and Chief Executive Officer

	 	 	 	 	 	 	 
	BANKS:	 	 	 	COMERICA BANK
	 
	 	 	 	 	 	 
	 

	 	 	 	By:	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Its:	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	FIFTH THIRD BANK
	 
	 	 	 	 	 	 
	 

	 	 	 	By:	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Its:	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	JPMORGAN CHASE BANK N.A.
	 
	 	 	 	 	 	 
	 

	 	 	 	By:	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Its:	 	 
	 

	 	 	 	 	 	 

[SIGNATURE PAGE TO AMENDMENT NO. 2 TO SECOND AMENDED AND

RESTATED CREDIT AGREEMENT]

 

 

EXHIBIT A

     The undersigned previously executed and delivered to Comerica Bank, as Agent, a Guaranty dated
June 30, 2006 (“Guaranty”) with respect to the obligations and liabilities of North Pointe Holdings
Corporation (“Borrower”) to Comerica Bank, Fifth Third Bank and JPMorgan Chase Bank N.A. The
undersigned acknowledge the foregoing amendment to the Amended and Restated Credit Agreement dated
July 2, 2007 between Borrower, Comerica Bank as Agent and the lenders party to the Credit
Agreement. The undersigned acknowledge and agree that the Guaranty remains in full force and
effect in accordance with its terms and that the undersigned have no defense or setoff to their
respective obligations under the Guaranty.

Dated: July 2, 2007

	 	 	 	 	 
	 	 	SOUTH POINTE FINANCIAL

SERVICES, INC.
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	John H. Berry
	 
	 	 	 	 
	 	 	Its: Treasurer
	 
	 	 	 	 
	 	 	NORTH POINTE FINANCIAL

SERVICES, INC.
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Brian J. Roney
	 
	 	 	 	 
	 	 	Its: Vice President
	 
	 	 	 	 
	 	 	N.P. PREMIUM FINANCE COMPANY
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	John H. Berry
	 
	 	 	 	 
	 	 	Its: Treasurerexv4w2

 

EXHIBT 4.2

REVOLVING CREDIT NOTE

			
	$10,500,000
	 	July 2, 2007

     On the Revolving Credit Maturity Date, FOR VALUE RECEIVED, North Pointe Holdings Corporation,
a Michigan corporation (“Company”) promises to pay to the order of Fifth Third Bank (“Bank”) care
of Comerica Bank, as Agent, at 500 Woodward Avenue, Detroit, MI 48226, in lawful money of the
United States of America, the sum of Ten Million Five Hundred Thousand Dollars ($10,500,000), or so
much of said sum as may from time to time have been advanced and then be outstanding hereunder
pursuant to the Second Amended and Restated Credit Agreement dated as of June 30, 2006, made by and
among the Company, certain banks, including the Bank, and Comerica Bank as Agent for such banks, as
the same may be amended from time to time (the “Agreement”), together with interest thereon as
hereinafter set forth.

     Each of the Advances made hereunder shall bear interest at the Applicable Interest Rate from
time to time applicable thereto under the Agreement or as otherwise determined thereunder, and
interest shall be computed, assessed and payable as set forth in the Agreement.

     This Note is a note under which advances (including refundings and conversions), repayments
and readvances may be made from time to time, but only in accordance with the terms and conditions
of the Agreement. This Note evidences borrowings under, is subject to, is secured in accordance
with, and may be accelerated or matured under, the terms of the Agreement, to which reference is
hereby made. Definitions and terms of the Agreement are hereby incorporated by reference herein.

     This Note shall be interpreted and the rights of the parties hereunder shall be determined
under the laws of, and enforceable in, the State of Michigan.

     Company hereby waives presentment for payment, demand, protest and notice of dishonor and
nonpayment of this Note and agrees that no obligation hereunder shall be discharged by reason of
any extension, indulgence, release, or forbearance granted by any holder of this Note to any party
now or hereafter liable hereon or any present or subsequent owner of any property, real or
personal, which is now or hereafter security for this Note.

     Nothing herein shall limit any right granted Bank by any other instrument or by law.

     This Note amends, restates, supersedes, replaces and increases that certain Revolving Credit
Note dated as of June 30, 2006, made in the principal amount of Seven Million Five Hundred Thousand
Dollars ($7,500,000) by Company payable to Bank, and the initial Advance(s) under this Note shall
be deemed first applied, to the extent necessary, to repay the existing indebtedness of Company to
Bank under said Note; provided, however, the execution and delivery by Company of this Note shall
not, in any manner or circumstance, be deemed to be a novation of or to have terminated,
extinguished or discharged any of Company’s indebtedness

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evidenced by said Note, all of which indebtedness shall continue under and shall hereinafter
be evidenced and governed by this Note.

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	 	 	NORTH POINTE HOLDINGS

CORPORATION, a Michigan corporation
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 
Its:
	 	James G. Petcoff

Chairman and Chief Executive Officer

[SIGNATURE PAGE TO REVOLVING CREDIT NOTE (FIFTH THIRD BANK)]

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