Challenging Logins | Explore cascading security vulnerabilities in login workflows | Exploratory Testing

Note: From the below post, "Prompt Template" and "Example Usage" are for you to copy/modify/reuse. The remaining fields are added for you to gain more knowledge about the Prompt. Happy learning!

Challenging Logins | Explore cascading security vulnerabilities in login workflows | Exploratory Testing | Chain-of-Thought Prompt

Purpose
Challenging Logins | Explore cascading security vulnerabilities in login workflows | Exploratory Testing | Chain-of-Thought Prompt

QE Category
Exploratory Testing

Prompt Type
Chain-of-Thought

Typical SUTs and Quality Phases
Exploratory testing focusing on identifying, exploiting, and mitigating cascading vulnerabilities in login workflows.

Prompt Template

Role: Security-focused exploratory tester uncovering cascading vulnerabilities.
Context: You are testing login workflows for a system where the username is an email address. The goal is to explore cascading vulnerabilities from an initial information leak to potential misuse scenarios.
Task: Follow these sequential steps:
1. Identify information leakage vulnerabilities:
- Test random email-password combinations.
- Observe if the system reveals whether the username (email) exists, such as through an 'Incorrect Password' message.
- Hypothesis: Revealing username validity might allow attackers to target specific accounts.
2. Exploit the leaked information:
- Use the identified valid email address to generate likely passwords.
- Test these passwords systematically, observing outcomes such as successful login or account lockout.
- Hypothesis: Likely passwords combined with brute force could compromise accounts or trigger a lockout.
3. Simulate the misuse of vulnerabilities:
- Draft a fake email pretending to be from the system's support team.
- The email warns the user about repeated lockouts and demands money to stop the attacks.
- Hypothesis: Such phishing emails might exploit user anxiety caused by the vulnerability.
Instructions: Document findings at each step. Use these findings to design mitigation strategies and explore how interconnected vulnerabilities escalate security risks.
Output: Generate exploratory tests with the following details:
- Test Charter
- Hypothesis
- Challenges
- Test Ideas
- Approximate Timebox
- TODO: Ask the tester to log observations and share results.
Output: Generate exploratory tests with the following details:
- Test Charter
- Hypothesis
- Challenges
- Test Ideas
- Approximate Timebox
- TODO: Ask the tester to log observations and share results.
Output: Generate exploratory tests with the following details:
- Test Charter
- Hypothesis
- Challenges
- Test Ideas
- Approximate Timebox
- TODO: Ask the tester to log observations and share results.

Example Usage

Role: Security-focused exploratory tester uncovering cascading vulnerabilities.
Context: You are testing login workflows for a system where the username is an email address. The goal is to explore cascading vulnerabilities from an initial information leak to potential misuse scenarios.
Task: Follow these sequential steps:
1. Identify information leakage vulnerabilities:
- Test random email-password combinations.
- Observe if the system reveals whether the username (email) exists, such as through an 'Incorrect Password' message.
- Charter: Identify information leakage vulnerabilities in login workflows.
2. Exploit the leaked information:
- Use the identified valid email address to generate likely passwords.
- Test these passwords systematically to observe successful login attempts or account lockouts.
- Charter: Investigate the impact of username leakage on account security.
3. Simulate the misuse of vulnerabilities:
- Draft a fake phishing email pretending to be from the system's support team.
- Warn the user about repeated lockouts and demand money to stop attacks.
- Charter: Explore how vulnerabilities might be exploited for social engineering attacks.
Instructions: Document findings at each step and design mitigation strategies to address cascading vulnerabilities in login workflows.
Output: Generate exploratory tests with the following details:
- Test Charter
- Hypothesis
- Challenges
- Test Ideas
- Approximate Timebox
- TODO: Ask the tester to log observations and share results.
Output: Generate exploratory tests with the following details:
- Test Charter
- Hypothesis
- Challenges
- Test Ideas
- Approximate Timebox
- TODO: Ask the tester to log observations and share results.

Tested in GenAI Tools
Extensively optimized for ChatGPT, Claude, Microsoft Copilot, Google Gemini, and Perplexity -- delivering reliable and actionable results across leading GenAI platforms.

Customized Prompt Engineering Techniques

Use exploratory charters to focus each step on a specific vulnerability, like username leakage or brute-force attacks.
Include scenarios where attackers might use machine-generated phishing emails for mass targeting.
Extend Step 3 to test phishing awareness among users by simulating realistic email responses.

Value of the Prompt
Demonstrates how small vulnerabilities can escalate into serious security risks when interconnected. Encourages testers to think critically and explore mitigation strategies.

Tips and Best Practices

Instructions for Use: Treat each step as part of a broader security narrative. Connect findings systematically to uncover cascading vulnerabilities.
Document observed weaknesses and their potential impact, linking them to real-world exploitation scenarios.
Propose mitigations for each identified vulnerability to enhance system security.

Hands-On Exercise
Simulate the described flow on a test environment. Begin by probing for username leakage, exploit identified weaknesses systematically, and conclude by drafting social engineering scenarios.

Appendix and Additional Information

Further Reading -- 'The Web Application Hacker’s Handbook' by Dafydd Stuttard and Marcus Pinto. This book covers cascading vulnerabilities and their real-world implications.
Additional Learning -- Study social engineering techniques and phishing mitigation strategies.

Want More?
Extend this chain to explore advanced scenarios, such as using automation tools for brute-force attacks or testing multi-factor authentication vulnerabilities.

Author
Ashwin Palaparthi

[kkstarratings]

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