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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 complex login scenarios with multiple examples | Exploratory Testing | Multi-Shot Prompt

Purpose
Challenging Logins | Explore complex login scenarios with multiple examples | Exploratory Testing | Multi-Shot Prompt

QE Category

Prompt Type
Multi-Shot

Typical SUTs and Quality Phases
Exploratory testing during test design and execution, leveraging 3+ examples to uncover complex issues.

Prompt Template

Role: A maverick exploratory tester investigating login scenarios with increasing complexity.
Context: Focus on interconnected login workflows to uncover edge cases and security vulnerabilities.
Task: Generate exploratory scenarios based on Hypothesis and Heuristics.
Focus on:
- Generate basic [Login Edge Cases], such as empty fields and invalid characters.
- Progress to layered attacks, like chained SQL injections combined with malformed payloads.
- Explore [Complex Session Management], such as token invalidation during multi-device logins.
- Analyze workflows involving dependent actions, like login followed by file uploads.
Instructions: Generate progressive exploratory test scenarios starting from simple cases to complex ones. Document each scenario in detail, ask the tester to submit the results as the next prompt, so that you can iterate based on observed results to refine the next steps.
Examples:
1. Test login attempts using empty username and password fields.
2. Explore behavior when passwords contain emojis or mixed encodings.
3. Simulate chained SQL injections combined with invalid payload formats.
4. Investigate simultaneous logins under rapid token expiration.
5. Analyze token invalidation and its effect on in-progress tasks, such as file uploads.
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: A maverick exploratory tester investigating login scenarios with increasing complexity.
Context: Focus on interconnected login workflows to uncover edge cases and security vulnerabilities.
Task: Generate exploratory scenarios based on Hypothesis and Heuristics.
Focus on:
- Generate basic login edge cases, like empty fields and invalid input formats.
- Progress to layered scenarios, such as combined SQL injections and malformed payloads.
- Explore complex session management, like token expiration during concurrent logins.
- Analyze workflows with dependent actions, such as login followed by file uploads.
Instructions: Generate progressive exploratory test scenarios starting from simple cases to complex ones. Document each scenario in detail, ask the tester to submit the results as the next prompt, so that you can iterate based on observed results to refine the next steps.
Examples:
1. Test login attempts with empty username and password fields.
2. Investigate behavior with mixed encoding in passwords, including emojis.
3. Combine chained SQL injections with malformed data payloads.
4. Simulate rapid token expiration during concurrent logins.
5. Analyze the system's response when token invalidation disrupts ongoing file uploads.
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

  1. Combine SQL injection tests with password brute-forcing to simulate real-world attacks.
  2. Explore edge cases involving mixed input encodings.
  3. Design tests around intentionally delayed session token renewals.

Value of the Prompt
Encourages testers to tackle complex scenarios by providing progressively challenging examples, ensuring comprehensive exploration of login workflows.

Tips and Best Practices

  1. Start with simpler examples to understand system responses, then layer complexity.
  2. Focus on scenarios that challenge session integrity, such as overlapping tokens.
  3. Track findings carefully to inform future security and performance improvements.

Hands-On Exercise
Investigate login workflows for a ride-sharing app. Start with SQL injection attempts and progress to simultaneous device logins.

Appendix and Additional Information

  1. Further Reading: 'The Web Application Hacker’s Handbook' by Dafydd Stuttard and Marcus Pinto. This book dives deep into vulnerabilities like SQL injection and token mismanagement.
  2. Additional Learning: Study session management in distributed systems.

Want More?
Create layered attacks with combinations of malformed payloads and simulated bot behaviors. Push boundaries to uncover deeper issues!

Author
Ashwin Palaparthi

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