Grey-Box Penetration Testing: Steps and Assessment Criteria

Learning Outcomes and Assignment Brief

This Assignment assesses the following module Learning Outcomes (from Definitive Module Document):

1. Critically analyse and evaluate security techniques used to protect complex heterogeneous environments and apply their findings for offering advice regarding solutions to decision makers.
2. Apply advanced and current concepts/issues of computer systems risks, vulnerabilities, threats analysis, and software security in the context of a penetration test
3. Use initiative for autonomously conducting and managing a penetration test, within a complex and unpredictable environment, demonstrating a systematic approach of creatively applying knowledge in unfamiliar contexts for solving problems

Assignment Brief:

Assume that you are working as a consultant for an SME which is building its capability in penetration testing. Your client has asked your employer to conduct the penetration test against a server, as they fear they might have already been breached. To their best of their knowledge, the company assumes that the server offers only the following online services: http, b) ssh, and c) vnc.

Task 3

You are expected to undertake a grey-box Penetration Test. To guide your activities, you are expected

to use the plans that you have produced in Assignment 1.

Information about the IP address of target of your test as well as the schedule to access it is available on

Canvas. Specifically, please navigate to the module on Canvas and select the “Your Assignment IP address and your Access Schedule” page, which is available under the “Module Information” Unit, in order to find more information.

Please look at the Assessment Criteria table, which is provided below, for understanding the expected structure of your report. You are required to present your findings in a factual manner to convince decision makers of a large corporation on business strategies. Do not provide a narrative of your intelligence gathering activities in the main report. You may include this in an appendix.

In the Attack Narrative section, you are expected to discuss the attacks you have undertaken and what vulnerabilities you have tested in each attack. In the Vulnerability Details & Mitigation section you are expected to provide a technical explanation of the vulnerabilities you have tested and confirmed (e.g., with a working exploit), as well as offer advice on how to mitigate it. To get full marks for this section you are expected to provide confirmed details and mitigation for  that you have found on the target.

You must use the VPN for undertaking this assignment. You must use the allocated to you target (IP address) during your schedule. Failing to do this will result in the deduction of marks.

Submission Requirements:

You are required to submit a 1500 words text report in a PDF document using the submission link provided on Canvas. Please note it is your responsibility to ensure you will submit on time. Canvas is a stable platform with a large technical team supporting it. Apropos, it is a software platform. It is advisable to submit before the day of the deadline.

You are expected to demonstrate an insight into the implications of the problem introduced in each task by using clear and concise arguments. The report should be well written, showing good skills in creativity and design, as well as well-structured using sections and subsections to ensure its readability. Sentences should be of an appropriate length and the writing style should be brief but informative. Work that is not making sense will be marked down. Write to impress! Aim for excellence. Be pedantic about formatting and presentation.