Exhibit 10.1
 
AMENDMENT NO. 4 TO CONVERTIBLE DEBENTURE

This Amendment No. 4 (“Amendment”) to the Convertible Debenture in the original
principal amount of $15,149,650 dated June 30, 2006, as amended (the
“Convertible Debenture”) is made as of January 16, 2008, by and among YA Global
Investments, L.P. (f/k/a Cornell Capital Partners, LP), a Cayman Islands limited
partnership, with its principal place of business at 101 Hudson Street, Suite
3700, Jersey City, New Jersey 07302 (“YA Global”) and Mobilepro Corp. (the
“Company”).
 
WHEREAS, the Company owes YA Global weekly payments of $250,000 in principal
payments plus interest on the outstanding principal balance of the Convertible
Debenture commencing November 15, 2006;

WHEREAS, pursuant to Amendment No. 2 to Convertible Debenture YA Global agreed
to allow the Company to suspend all principal and interest payments under the
Convertible Debenture until July 8, 2007;

WHEREAS, the Company executed on June 29, 2007 a Purchase Agreement pursuant to
which it sold certain of its telephony businesses to United Systems Access, Inc.
d/b/a USA Telephone to enable it to extinguish all principal and interest owed
under the terms of the Convertible Debentures as those businesses are sold in
stages through December 31, 2007; and

WHEREAS, pursuant to the above Purchase Agreement USA Telephone agreed to pay
$2,000,000 of the purchase price at the earlier of January 1, 2008 or the second
closing of the ISP companies pursuant to a Promissory Note dated June 29, 2007
(the “Note”); and

WHEREAS, USA Telephone has informed the Company that it cannot make the
$2,000,000 Note payment on January 1, 2008 but intends to pay $500,000 by
January 4, 2008 , an additional $500,000 by January 11, 2008 and the remaining
$1,000,000 at the earlier of the Second Closing (as that term is defined in the
Purchase Agreement) or March 31, 2008; and

WHEREAS, the Company executed contemporaneously with the above Purchase
Agreement Amendment No. 3 to Convertible Debentures to suspend all Scheduled
Payments until January 1, 2008; and
 
WHEREAS, as a result of the delay in the closing of the sale of the CLEC assets
of Mobilepro, the Company requests YA Global to extend for thirty (30) days
until February 1, 2008 payment of principal and interest payments under this
Agreement; and

WHEREAS, the Company intends to pay YA Global $500,000 on January 4, 2008 and
$375,000 on January 11, 2008 when USA makes the Note payments in early January
2008 and all $1,000,000 of the Note payment when USA makes the remaining Note
payment at the earlier of the Second Closing (as that term is defined on the
Purchase Agrement) or March 31, 2008; and

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WHEREAS, the parties to this Agreement desire to amend the Convertible
Debentures to defer all principal and interest payments until February 1, 2008.

NOW THEREFORE, in consideration of the foregoing, and for other good and
valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties hereto agree as follows:

Section 1. Amendment to Section 1.02 of the Convertible Debenture. Section 1.02
of the Convertible Debenture is hereby amended and restated in its entirety as
follows:

Section 1.02 Payments.

(a) The Company shall be required to make weekly scheduled payments (“Scheduled
Payments”) consisting of at least $250,000 of principal, commencing with the
first Scheduled Payment which shall be due and payable on February 1, 2008.
Interest payments on the outstanding principal balance hereof shall commence on
February 1, 2008. The Company shall have the right to make each Scheduled
Payment in shares of Common Stock, which shares shall be valued at the lower of
$0.275 or a seven percent (7%) discount to the average of the two lowest daily
volume weighted average prices of the Company’s Common Stock as quoted by
Bloomberg, LP for the five (5) trading days immediately following the Scheduled
Payment date (the “Payment Conversion Price”), provided that all such shares may
only be issued by the Company if such shares are tradeable under Rule 144 of the
Securities and Exchange Commission (the “Commission”), are registered for sale
under the Securities Act of 1933 or are freely tradeable without restriction in
the hands of the Holder. All payments in respect of the indebtedness evidenced
hereby shall be made in collected funds (unless paid in shares of Common Stock),
and shall be applied to principal, accrued interest and charges and expenses
owing under or in connection with this Debenture in such order as the Holder
elects, except that payments shall be applied to accrued interest before
principal. Notwithstanding the foregoing, this Debenture shall become due and
immediately payable, including all accrued but unpaid interest, upon an Event of
Default (as defined in Section 3.01 hereof). Whenever any payment or other
obligation hereunder shall be due on a day other than a business day, such
payment shall be made on the next succeeding business day. Time is of the
essence of this Debenture. The Company shall be permitted to prepay any amounts
owed under this Debenture if the price of the shares of the Company’s Common
Stock is less than $0.275 per share and also may, at its option, increase any
scheduled payment to $750,000 (payable in cash or Common Stock as set forth
above) without incurring any penalties or fees. Nothing contained in this
paragraph shall limit the amount that the Holder can convert at any time.
 
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Section 2. Effect of Amendment. Except as amended hereby, the Convertible
Debenture shall continue in full force and effect and is hereby incorporated
herein by this reference. 

Section 3. Governing Law. This Amendment shall be governed by and construed
under the laws of the State of New Jersey.  

Section 4. Titles and Subtitles. The titles of the sections and subtitles of
this Amendment are for convenience of reference only and are not to be
considered in construing this Amendment.

Section 5. Counterparts. This Amendment may be executed in counterparts, each of
which shall be deemed an original, and all of which shall constitute one and the
same instrument.

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IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be signed
as of the date first set forth above.

 
MOBILEPRO CORP.
         
By:
/s/ Jay O. Wright    
Name: Jay O. Wright
   
Title: Chairman and CEO
         
YA GLOBAL INVESTMENTS L.P.
         
By:
/s/ Troy Rillo    
Name: Troy Rillo
   
Its: Senior Managing Director

 
 
Signature Page to Amendment No. 4 to Convertible Debenture
 
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