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Interview question · Prompt Injection & Jailbreaks

How do encoding and payload splitting get past filters, and what does that say about filter design?

Find representation and context mismatches without assuming a universal bypass. Place checks before the real release, preserve source authority and keep legitimate decoding useful.

mediumNewUpdated Nov 2026

Find representation and context mismatches without assuming a universal bypass. Place checks before the real release, preserve source authority and keep legitimate decoding useful.

Make your first attempt

What would you say before reading the answer?

  1. 01 State the assumptions your answer depends on.
  2. 02 Explain the mechanism and choose a control.
  3. 03 Name a condition that would change your decision.

The worked answer includes an approach, scoring criteria and follow-up questions. Compare the reasoning with your own.

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What if · the follow-ups in this answer

The answer works through 4 follow-ups like an interviewer would

Mateo explains exported support records containing prose, a declared encoded attachment field and earlier-message references. Customer delivery needs a separate audience grant.

  1. What if the input checker already inspects the decoded attachment?
  2. What if the answer filter blocks the response after a send tool completed?
  3. What if a customer legitimately needs the encoded export?
  4. What should a reviewer be able to verify?

Each rung has a nudge, a model answer, the principle that carries over and the weak answer to avoid. Premium opens every answer and ladder.

UP NEXT ON YOUR JOURNEY
Next in this trackWhat are invisible-character tricks in prompt injection, and where should text be normalised?Next in this trackArchitect a prompt injection detection system for production and show how you would know it works.Next in this trackWhat is a canary token in an LLM application, and what can it detect?
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