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

    


    
      
        
        

      

      
        
        

        
          

        

      

      
        
        

      

    

    


    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.

     

    
      
        
        

      

      
        -
          2
          -

        
          

        

      

      
        
        

      

    

     

    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.

    


    
      
        
        

      

      
        -
          3
          -

        
          

        

      

      
        
        

      

    

    


    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 

     

    
      
        
        

      

      
        -
          4
          -