1. Vulnerability Assessment and Penetration Test Exercise (Individual)
1.1 Project Overview
Artworks Pte Ltd is a Singapore-based SME that is well-known for displaying high-profile artwork in a virtual setting. The business has just won a local productivity award using cloud technologies to run their virtual gallery platform called ‘The Artisan’s Gallery’.
The client had called (as part of an annual internal review) a tender to perform a Vulnerability Assessment and Penetration Test (VAPT) on a specific set of assets hosted on the Staging environment before being pushed to the production cloud. The awarded vendor is to report any findings and provide recommendations.
Your company, CDF Pte Ltd, has responded to the tender and is awarded the deal. Your managing consultant has assigned your team to perform the assessment for Artworks Pte Ltd.
This assessment allows you to ethically use AI tools as collaborative partners in planning, structuring, and evaluating your work. You are required to critically reflect on your use of AI and verify the accuracy of all AI-supported work.
1.2 General Requirements
- Students are to form groups of 4 to 5 for this assignment. The main objective for all groups is to identify and exploit security vulnerabilities on 3 target machines (CS-BOX1, CS-BOX2, CS-BOX3).
- Each target is configured with 3 levels of challenges, and the logical network diagram for each target is shown below:
- A quick descriptions of the levels are as follows:
- LEVEL1 – Network vulnerability assessment & penetration testing
- LEVEL2 – Web application vulnerability assessment & penetration testing
- LEVEL3 – ‘RANDOM CATEGORY’ vulnerability assessment & penetration testing
- Each level is also designed with the following exploits that you are to discover during your case study attempt:
- Initial Entry / Initial Exploitation (security misconfiguration / vulnerability to low-privileged user)
- Privilege Escalation Exploit (low-privileged user to high-privileged root user)
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- The table below shows an overview of vulnerabilities (14 vulnerabilities in total) for all three target boxes:
CS-BOX1 | CS-BOX2 | CS-BOX3 |
---|---|---|
LEVEL1 1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
LEVEL2 1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
LEVEL3 (ALL THREE TARGETS SHARE THE SAME LEVEL3 CHALLENGE) 1x Initial Entry / Initial Exploitation 1x Privilege Escalation Exploit |
- Each student in the group is to do a write-up on ONE vulnerability (initial entry OR privilege escalation) on any one of the level challenges (except LEVEL3). Template for the writeup will be provided in POLITEMall.
- Attempt for the LEVEL3 challenge is OPTIONAL as it covers another set of topics that are NOT included in this module, which is on Binary Exploitation. If you require additional resources for this challenge, you can visit the following website for more information:
- https://ctf101.org/binary-exploitation/overview/
- More marks will be awarded for successfully exploiting (EITHER getting low privileges OR full ‘root’/administrative access of the target machine) a higher-level challenge due to the effort and complexity of the challenge, except for the LEVEL3 challenge which bears no additional marks.
- Use AI tools ethically and document how they were used:
- Which AI tool(s) you used
- How you used it (e.g., structuring ideas, debugging scripts)
- Critically evaluate and reflect on the accuracy and usefulness of AI support.
- You are NOT to perform vulnerability assessments and penetration tests beyond the scope given, such as scanning other networks and systems. Anyone caught doing so could result in immediate failure of this subject or even more severe disciplinary action.
1.3 AI Tool Usage Guidelines
- Students may use AI for:
- Brainstorming and planning testing strategies
- Clarifying technical concepts
- Structuring and editing the report
- Suggesting exploit techniques (to be tested and verified manually)
- Debugging scripts (e.g., Bash, Python)
- Providing feedback or summarizing documentation
- Do NOT use AI for:
- Fabricating or simulating test results
- Submitting content without critical review or personal understanding
- Sharing AI-generated answers without verification
1.4 Submission Requirements
- All groups are to submit a combined report that contains the following:
- Cover Page
- Declaration of Originality (with complete signatures)
- Executive Summary
- Findings Overview
- Detailed Findings and Recommendations (compiled finding writeups written by all 4-5 members)
- For the title of each finding, you are only allowed to use ONE title per vulnerability. Here is the list of accepted titles:
- Misconfigured Scheduled Task Permissions
- Weak/Known Password of User Account ‘___________’
- Misconfigured Sudo Privileges
- Default/Weak Administrator Password
- SQL Injection
- Cross-Site Scripting (Stored)
- For more information regarding the various sections of the report template, view the comments for more information.
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Get A Free Quote - You are expected to submit the Final Report as a PDF document with all the necessary requirements listed 1.3(a). To generate the PDF file, follow the instructions below:
- Open your Word document and go to File > Save as Adobe PDF
- Once done, go to Options and ensure that you tick the following boxes:
- Create Bookmarks
- Convert Word Headings to Bookmarks
- Be warned that plagiarism is a serious offence!
Students are to submit via Brightspace LMS based on the stipulated deadline specified in the Teaching Plan. Submissions via any other communication channels (e.g Emails, WhatsApp, Microsoft Teams) will not be accepted.
Late submissions:
- Late and < 1 day: 10% deduction from absolute mark given for the assignment. E.g., 75 marks (100 marks max) → 65 marks (10% of 100 marks).
- Late ≥ 1 and < 2 days: 20% deduction from the absolute mark.
- Late ≥ 2 days: No marks awarded.
1.5 Marking Rubrics
Each individual finding in the report – 30% (in Section 4 of your Case Study Report) will be evaluated based on the following criteria:
Criteria (5m each) | Description / Expectation |
---|---|
CVSSv3.1 Calculation | • Risk Rating, Vector String and Risk Score are all thoroughly checked, appropriate and in unison. • The chosen CVSS metric values must be reflected/described inside the Impact and Technical Details section of the finding to show the synergy of the finding. |
Impact | • Explains the impact of the vulnerability as listed in the CVSS metric value selected. • It must be in sync with both the CVSSv3.1 Calculation and Technical Details section of the finding. |
Technical Details | • Steps are well-documented and presented sequentially. • Example payloads/commands are provided and the expected outcomes are shown as part of the replication of steps. • Replication of steps are supplemented with screenshots that are relevant to depict the steps taken. |
Recommendation | • Provided recommendation is clear, succinct and actionable, allowing the client to perform the necessary steps to fix the vulnerability if possible. • Links/sources to support the recommendations are also included. |
References | • Identify at least the Common Weakness Enumeration (CWE) and Common Attack Pattern Enumeration and Classification (CAPEC) reference numbers for the vulnerability. |
Affected Assets and Formatting | • Formatting of the headers and text are justified in alignment. • Correct use of affected assets table based on the nature of the documented vulnerability. • Images are properly resized to reduce unnecessary whitespaces within the report. |
2. Findings Walkthrough Presentation (Individual)
2.1 Overview
After performing the vulnerability assessment and penetration test exercise with your team, the Head of IT has instructed your team to conduct a walkthrough of your report with him. As the Head of IT has a bad experience with previous penetration testing vendors submitting quite several false positives to the organisation, he tends to be far more wary and will tend to second-guess every single detail that is being listed out in the report.
Your team is confident of the submitted vulnerabilities and will do whatever it takes to prevent the Head of IT from discouraging you to remove the vulnerabilities due to the lack of supporting evidence.
2.2 Presentation Requirements
- Only the submitted PDF report will be used for the walkthrough. No demonstrations or PowerPoint slides are allowed.
- The template for the case study report dictates the flow of the presentation:
- Cover Page – The team Leader to introduce the team to the client.
- Executive Summary – The team Leader provides a quick overview of what the testing is about (e.g how long did it took, how many targets)
- Findings Overview – The team Leader to list the number of vulnerabilities that have been classified into their respective risk ratings.
- Detailed Findings and Recommendations – Team members are to step out one by one to present their vulnerabilities (no questions will be asked until the end of the presentation, assessor will take note of questions).
- Question and Answer segment will only be conducted at the end of the presentation.
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2.3 Marking Rubrics
For the Findings Walkthrough Presentation component – 10%, the following items will be assessed:
Report Criteria (2.5m each) | Description / Expectation |
---|---|
Executive Summary | Wrote introductory paragraph indicating the duration of the test. Wrote a summary for three or more findings, mentioned business impact and mentioned recommendations to fix findings. Provide recommendations to client on how to improve the overall security posture for the organization. |
Findings Overview | Names of findings, their respective risk ratings, and the total number of findings per risk rating are correct based on the report content. List of findings is presented and arranged in sequential order, from Critical to Advisory findings (top to bottom) |
Presentation Criteria (2.5m each) | Description / Expectation |
---|---|
Findings Defense | Is the tester able to defend the finding based on the requirements of the client? |
Presentation & Professionalism | Is the team able to use the sequencing of the report as part of the presentation workflow? (e.g Executive Summary, Findings Overview, Detailed Findings) Is the team able to provide an opinion as to what findings should be fixed first to the client? (consider time and complexity of the fixes). |
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