Most bad outputs are not mysterious. They trace back to a small number of preventable mistakes, two of which (injection and leakage) are security problems rather than writing problems.
Missing context
The model fills gaps with the statistically typical case, which is rarely yours. A request with no audience, purpose or constraints produces a fluent average.
Ask: Who is this for, what will they do with it, and what do I know that the model cannot?
Repair: Add two or three sentences of situation. Paste the actual error, document or data instead of describing it.
Invented sources (confabulation)
Language models can produce plausible citations, statistics and quotes that do not exist. NIST AI 600-1 lists confabulation among its generative-AI risks; OWASP's 2025 list includes misinformation (LLM09).
Ask: Could I check every factual claim in the answer, and did I give the model a way to say “I don't know”?
Repair: Ground answers in material you supply, require checkable references, and give an explicit UNVERIFIED or 'not stated' escape hatch. Then actually check.
Over-constraint
Piling on absolute rules (always, never, exactly) creates contradictions and crowds out the goal. The model satisfies the easiest rules and quietly drops the important one.
Ask: If two of my rules conflicted, which would I want to win?
Repair: Keep rules that protect the outcome; convert style wishes into one example. Rank priorities explicitly.
Leakage
Prompts get logged, shared, pasted into tools and sometimes reflected back. OWASP's 2025 list names sensitive information disclosure (LLM02) and system prompt leakage (LLM07).
Ask: Would I be comfortable if this whole prompt appeared in a screenshot?
Repair: Redact before sending. Never put keys or passwords in prompts. Do not rely on a system prompt staying secret.
Prompt injection
Text the model reads (a web page, email, PDF) can contain instructions that override yours. OWASP ranks prompt injection first (LLM01:2025) and notes there may be no fool-proof prevention, only mitigations.
Ask: Does my prompt mix my instructions with content written by someone else?
Repair: Delimit untrusted content, state that it is data, limit what tools can do, and require human approval for consequential actions. Wording alone is not a security control.