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Exhibit 4.4    
  

 
 

THIRD AMENDMENT TO LOAN AGREEMENT    
  

        THIS THIRD AMENDMENT TO LOAN AGREEMENT (the "Third Amendment") is entered into as of the 29th day of September,
2002, by and between PIONEER DRILLING SERVICES, LTD., a Texas limited partnership, formerly known as Pioneer Drilling Co., Ltd.,
("Borrower"), and THE FROST NATIONAL BANK, a national banking association
("Lender") and joined in by PIONEER DRILLING COMPANY, a Texas corporation, formerly known as South Texas
Drilling & Exploration, Inc. ("Pioneer"). 

R E C I T A L S 

        A.    On
March 30, 2001, Borrower and Lender entered into that certain Loan Agreement (the "Agreement") concerning the
terms, conditions and covenants of certain Credit Facilities. On October 9, 2001, Borrower and Lender amended the Agreement by execution of that certain First Amendment to Loan Agreement. On
July 3, 2002, Borrower and Lender amended the Agreement by execution of that certain Second Amendment to Loan Agreement. 

        B.    Borrower
has requested and Lender has agreed to renew, extend and increase the Advance Facility. 

        C.    Lender
and Borrower have also agreed to amend the Agreement as contained herein to modify certain financial covenants contained therein. 

        D.    All
capitalized terms not otherwise defined in this Third Amendment shall have the same meanings as are set forth in the Agreement. 

        NOW,
THEREFORE, for and in consideration of the mutual covenants and promises herein contained, Lender and Borrower agree as follows: 

AGREEMENTS 

        1.    Section 1
is deleted in its entirety and the following is substituted in its place: 

        1.    Credit Facilities. Subject to the terms and conditions set forth in this Loan Agreement and the other agreements,
instruments and documents evidencing, securing, governing, guaranteeing and/or pertaining to the Loans, as hereinafter defined (collectively, together with the Loan Agreement, referred to hereinafter
as the "Loan Documents"), Lender hereby agrees to provide to Borrower the credit facility or facilities hereinbelow (whether one or more, the
"Credit Facilities"): 

Advance Facility.    Subject to the terms and conditions set forth herein, Lender agrees to lend to Borrower, on a non-revolving basis from
time to time during the period commencing on the date hereof and continuing through the maturity date of the promissory note evidencing this Credit Facility from time to time, an aggregate amount not
to exceed $8,000,000.00 in multiple advances, as may be requested by Borrower from time to time (the "Advance Facility"). Borrower shall not be allowed
to reborrow under the Advance Facility after a repayment. All sums advanced under the Advance Facility shall be used for such purposes as approved by Lender in Lender's sole and absolute discretion. 

        All
advances under the Credit Facilities shall be collectively called the "Loans". Lender reserves the right to require Borrower to give
Lender not less than one (1) business day prior notice of each requested advance under the Credit Facilities, specifying (i) the aggregate amount of such requested advance,
(ii) the requested date of such advance, and (iii) the purpose for such advance, with such advances to be requested in a form satisfactory to Lender. 

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        2.    The
definition of Cash Flow Coverage Ration in Section 9, subsection (b) is deleted in its entirety and the following is substituted in its place: 

Net
Income + Interest + Taxes + Depreciation + Amortization—

Distributions or Dividends—Maintenance Capital Expenditures

Current Portion of Long-Term Debt + Interest Expense + Cash Taxes Paid 

        3.    The
definition of Debt to Worth Ration in Section 9, subsection (c) is deleted in its entirety and the following is substituted in its place: 

        (c)  Debt to Worth Ratio. Borrower will maintain, at all times, to be tested quarterly on the last day of each fiscal quarter
of Borrower, a ratio of (a) total liabilities (excluding any Subordinated Debt), to (b) Tangible Net Worth plus Subordinated Debt of not
greater than 1.00 to 1.0. 

        4.    As
a condition precedent to Lender's obligation to make advances under the Advance Facility, Borrower shall have paid to Lender an Origination Fee (payable upon execution
of this Third Amendment) in the amount of $20,000.00. 

        5.    Except
as specifically modified or amended herein, all terms, provisions and requirements of the Agreement shall remain as written, and as amended from time to time.
Borrower hereby reaffirms all covenants, conditions, representations and warranties contained in the Agreement, as amended by this Third Amendment. 

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        IN
WITNESS WHEREOF, the parties hereto have caused this Third Amendment to be duly executed as of the date first above written. 

	 BORROWER:	 	LENDER:
	

PIONEER DRILLING SERVICES, LTD., a Texas limited partnership formerly known as Pioneer Drilling Co., Ltd., a Texas limited partnership	
 	
THE FROST NATIONAL BANK

a national banking association
	

By:	
 	

PDC Mgmt. Co., a Texas corporation, General Partner	
 	

By:	
 	

        

	 	 	 	 	 	 	 	Printed Name:	 
	 	 	 	 	 	 	 	 	 	 	

	 	 	 	 	 	 	 	Title:	 	        

	

 	
 	

By:	
 	

        
	
 	

 	
 	

 	

 
	 	 	Printed Name:	 	 	 	 	 	 
	 	 	 	 	 	
	 	 	 	 	 
	 	 	Title:	 	        
	 	 	 	 	 
	

AGREED TO:	
 	

 	
 	

 	

 
	
PIONEER DRILLING COMPANY, a Texas corporation, formerly known as South Texas Drilling & Exploration, Inc., a Texas corporation (executing for purposes of joining in certain
specific provisions, as noted above)	
 	

 	
 	

 	

 
	

By:	
 	

        
	
 	

 	
 	

 	

 
	Printed Name:	 	        
	 	 	 	 	 
	Title:	 	        
	 	 	 	 	 

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Exhibit 4.4

THIRD AMENDMENT TO LOAN AGREEMENTQuickLinks
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Exhibit 4.5    
  

 
 

PROMISSORY NOTE
  (Floating Rate)    

	$8,000,000.00	 	 	 	September 29, 2002

        For
value received, PIONEER DRILLING SERVICES, LTD., a Texas limited partnership (formerly known as Pioneer Drilling
Co., Ltd.), as principal ("Borrower"), promises to pay to the order of THE FROST NATIONAL BANK, a
national banking association ("Lender") at P.O. Box 1600, San Antonio, Texas 78296, or at such other address as Lender shall from time to time
specify in writing, the principal sum of EIGHT MILLION AND 00/100 DOLLARS ($8,000,000.00), or so much thereof as may be advanced pursuant to the terms of that certain Loan Agreement (herein so called)
dated March 30, 2001, as amended, in legal and lawful money of the United States of America, with interest on the outstanding principal from the date advanced until paid at the rate set out
below. Interest shall be computed on a per annum basis of a year of 360 days and for the actual number of days elapsed, unless such calculation would result in a rate greater than the highest
rate permitted by applicable law, in which case interest shall be computed on a per annum basis of a year of 365 days or 366 days in a leap year, as the case may be. 

        1.    Payment Terms.    Interest only shall be due and payable monthly as it accrues on the last day of each and every
calendar month, beginning October 31, 2002 and continuing regularly and monthly thereafter until June 30, 2003, when the entire amount hereof, principal and interest then remaining
unpaid, shall be then due and payable; interest being calculated on the unpaid principal each day principal is outstanding and all payments made credited to any collection costs and late charges, to
the discharge of the interest accrued and to the reduction of the principal, in such order as Lender shall determine. 

        2.    Late Charge.    If a payment is made 10 days or more late, Borrower will be charged, in addition to
interest, a delinquency charge of (i) 5% of the unpaid portion of the regularly scheduled payment, or (ii) $250.00, whichever is less. Additionally, upon maturity of this Note, if the
outstanding principal balance (plus all accrued but unpaid interest) is not paid within 10 days of the maturity date, Borrower will be charged a delinquency charge of (i) 5% of the sum
of the outstanding principal balance (plus all accrued but unpaid interest), or (ii) $250.00, whichever is less. Borrower agrees with Lender that the charges set forth herein are reasonable
compensation to Lender for the handling of such late payments. 

        3.    Interest Rate.    Interest on the outstanding and unpaid principal balance hereof shall be computed at a per
annum rate equal to the lesser of (a) a rate equal to the Prime Rate of Lender, plus one percent (1%) per annum, with said rate to be adjusted to reflect any change in said Prime Rate at the
time of any such change or (b) the highest rate permitted by applicable law, but in no event shall interest contracted for, charged or received hereunder plus any other charges in connection
herewith which constitute interest exceed the maximum interest permitted by applicable law, said rate to be effective prior to maturity (however such maturity is brought about). The "Prime Rate" shall
mean the prime rate of interest charged by Lender as established from time to time. The Prime Rate is a reference rate and does not necessarily represent the lowest or best rate actually charged to
any customer. 

        4.    Default Rate.    Matured unpaid principal and interest shall bear interest from date of maturity until paid at
(a) the highest rate permitted by applicable law, or (b) if no such maximum rate is established by applicable law, at the rate stated above plus five percent (5%) per annum. 

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        5.    Prepayment.    Borrower reserves the right to prepay, prior to maturity, all or any part of the principal of
this Note without penalty. Any prepayments shall be applied first to accrued interest and then to principal. Borrower will provide written notice to the holder of this Note of any such prepayment of
all or any part of the principal at the time thereof. All payments and prepayments of principal or interest on this Note shall be made in lawful money of the United States of America in immediately
available funds, at the address of Lender indicated above, or such other place as the holder of this Note shall designate in writing to Borrower. All partial prepayments of principal shall be applied
to the last installments payable in their inverse order of maturity. 

        6.    Default.    It is expressly provided that upon default in the punctual payment of this Note or any part hereof,
principal or interest, as the same shall become due and payable, or upon the occurrence of an
event of default specified in any of the other Loan Documents (as defined below) and such default continues after the giving of written notice to Borrower and the passage of the applicable cure period
as provided in the Loan Agreement, the holder of this Note may, at its option, without further notice or demand, (i) declare the outstanding principal balance of and accrued but unpaid interest
on this Note at once due and payable, (ii) refuse to advance any additional amounts under this Note, (iii) foreclose all liens securing payment hereof, (iv) pursue any and all
other rights, remedies and recourses available to the holder hereof, including but not limited to any such rights, remedies or recourses under the Loan Documents, at law or in equity, or
(v) pursue any combination of the foregoing; and in the event default is made in the prompt payment of this Note when due or declared due, and the same is placed in the hands of an attorney for
collection, or suit is brought on same, or the same is collected through probate, bankruptcy or other judicial proceedings, then the Borrower agrees and promises to pay all costs of collection,
including reasonable attorney's fees. 

        7.    Joint and Several Liability; Waiver.    Each maker, signer, surety and endorser hereof, as well as all heirs,
successors and legal representatives of said parties, shall be directly and primarily, jointly and severally, liable for the payment of all indebtedness hereunder. Lender may release or modify the
obligations of any of the foregoing persons or entities, or guarantors hereof, in connection with this loan without affecting the obligations of the others. All such persons or entities expressly
waive presentment and demand for payment, notice of default, notice of intent to accelerate maturity, notice of acceleration of maturity, protest, notice of protest, notice of dishonor, and all other
notices and demands for which waiver is not prohibited by law, and diligence in the collection hereof; and agree to all renewals, extensions, indulgences, partial payments, releases or exchanges of
collateral, or taking of additional collateral, with or without notice, before or after maturity. No delay or omission of Lender in exercising any right hereunder shall be a waiver of such right or
any other right under this Note. 

        8.    No Usury Intended; Usury Savings Clause.    In no event shall interest contracted for, charged or received
hereunder, plus any other charges in connection herewith which constitute interest, exceed the maximum interest permitted by applicable law. The amounts of such interest or other charges previously
paid to the holder of the Note in excess of the amounts permitted by applicable law shall be applied by the holder of the Note to reduce the principal of the indebtedness evidenced by the Note, or, at
the option of the holder of the Note, be refunded. To the extent permitted by applicable law, determination of the legal maximum amount of interest shall at all times be made by amortizing, prorating,
allocating and spreading in equal parts during the period of the full stated term of the loan and indebtedness, all interest at any time contracted for, charged or received from the Borrower hereof in
connection with the loan and indebtedness evidenced hereby, so that the actual rate of interest on account of such indebtedness is uniform throughout the term hereof. 

        9.    Security.    This Note has been executed and delivered pursuant to the Loan Agreement, and is secured by,  inter alia, that certain Security
Agreement dated March 30, 2001, executed by and between Pioneer Drilling Co., Ltd. and Lender, as
amended, covering certain collateral as more particularly described therein. This Note, the Loan Agreement and all other documents evidencing, securing, governing, guaranteeing and/or pertaining to
this Note, including but not limited to those documents 

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described above, are hereinafter collectively referred to as the "Loan Documents." The holder of this Note is entitled to the benefits and security
provided in the Loan Documents. 

        10.  Texas Finance Code.    In no event shall Chapter 346 of the Texas Finance Code (which regulates certain
revolving loan accounts and revolving tri-party accounts) apply to this Note. To the extent that Chapter 303 of the Texas Finance Code is applicable to this Note, the "weekly ceiling" specified in
such article is the applicable ceiling; provided that, if any applicable law permits greater interest, the law permitting the greatest interest shall apply. 

        11.  Governing Law, Venue.    This Note is being executed and delivered, and is intended to be performed in the
State of Texas. Except to the extent that the laws of the United States may apply to the terms hereof, the substantive laws of the State of Texas shall govern the validity, construction, enforcement
and interpretation of this Note. In the event of a dispute involving this Note or any other instruments executed in connection herewith, the undersigned irrevocably agrees that venue for such dispute
shall lie in any court of competent jurisdiction in Bexar County, Texas. 

        12.  Purpose of Loan.    Borrower agrees that no advances under this Note shall be used for personal, family or
household purposes, and that all advances hereunder shall be used solely for business, commercial, investment, or other similar purposes. 

        13.  Captions.    The captions in this Note are inserted for convenience only and are not to be used to limit the
terms herein. 

        14.  Financial Information.    Borrower agrees to promptly furnish such financial information and statements,
including financial statements in a format acceptable to Lender, lists of assets and liabilities, agings of receivables and payables, inventory schedules, budgets, forecasts, tax returns, and other
reports with respect to Borrower's financial condition and business operations as Lender may request from time to time. This provision shall not alter the obligation of Borrower to deliver to Lender
any other financial statements or reports pursuant to the terms of any other loan documents executed in connection with this Note. 

        15.  Renewal and Extension.    This Note is given in renewal and extension, but not extinguishment, of all amounts
left owing and unpaid on that certain promissory note dated March 29, 2002 executed and delivered by Pioneer Drilling Co., Ltd. and payable to the order of Lender in the original
principal face amount of $6,000,000.00. 

[Balance of Page Intentionally Left Blank]

[Signature Appears on Next Page]

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	 	 	BORROWER:
	

 	
 	

PIONEER DRILLING SERVICES, LTD., a Texas limited partnership (formerly known as Pioneer Drilling Co., Ltd.)
	

 	
 	

By:	
 	

PDC Mgmt. Co., a Texas corporation, General Partner
	

 	
 	

 	
 	

By:	
 	

	 	 	 	 	Printed Name:
	 	 	 	 	 	 	

	 	 	 	 	Title:	 	

4

QuickLinks

Exhibit 4.5

PROMISSORY NOTE (Floating Rate)

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