Penetration Testing

As a penetration tester, you are hired as a consultant by a small- to mid-sized business that is interested in calculating its overall security risk today, January 1, 2012. The business specializes in providing private loans to college students. This business uses both an e-Commerce site and point-of-sales devices (credit card swipes) to collect payment. Also, there exist a number of file transfer operations where sensitive and confidential data is transferred to and from several external partnering companies. The typical volume of payment transactions totals is approximately $100 million. You decide that the risk assessments are to take into account the entire network of workstations, VoIP phone sets, servers, routers, switches and other networking gear. During your interview with one of the business’s IT staff members, you are told that many external vendors want to sell security networking products and software solutions. The staff member also claimed that their network was too “flat.” During the initial onsite visit, you captured the following pertinent data to use in creation of the Penetration Test Plan.
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Non-stateful packet firewall separates the business’s internal network from its DMZ.
All departments–including Finance, Marketing, Development, and IT–connect into the same enterprise switch and are therefore on the same LAN. Senior management (CEO, CIO, President, etc.) and the Help Desk are not on that LAN; they are connected via a common Ethernet hub and then to the switched LAN.
All of the workstations used by employees are either Windows 98 or Windows XP. None of the workstations have service packs or updates beyond service pack one.
Two (2) Web servers containing customer portals for logging in and ordering products exist on the DMZ running Windows 2000 Server SP1, and IIS v5.
One (1) internal server containing Active Directory (AD) services to authenticate users, a DB where all data for the company is stored (i.e. HR, financial, product design, customer, transactions). The AD server is using LM instead of NTLM.
Write a six page paper in which you:
Explain the tests you would run and the reason(s) for running them (e.g. to support the risk assessment plan).
Determine the expected results from tests and research based on the specific informational details provided. (i.e., IIS v5, Windows Server 2000, AD server not using NTLM)
Analyze the software tools you would use for your investigation and reasons for choosing them.
Describe the legal requirements and ethical issues involved.
Using Visio or its open source alternative, provide a diagram of how you would redesign this business’ network. Include a description of your drawing. Note: The graphically depicted solution is not included in the required page length.
Propose your final recommendations and reporting. Explain what risks exist and ways to either eliminate or reduce the risk.
Use at least three (3) quality resources in this assignment. Note: Wikipedia and similar Websites do not qualify as quality resources.
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