Report #100886
[gotcha] Blind retries after LLM errors resubmit the same failing context and burn user trust
Classify errors before retrying: transient errors \(429/overloaded\_error, 5xx\) get exponential backoff with jitter; permanent errors \(content\_filter, context\_length\_exceeded, bad request\) surface to the user with editable context; mid-stream failures resume if the provider supports it. Preserve conversation state so the user never has to retype.
Journey Context:
OpenAI and Anthropic APIs return distinct error types, but most UIs collapse them into 'Something went wrong. Retry?' That wastes tokens and patience. Microsoft's Guidelines for Human-AI Interaction emphasize graceful failure and easy recovery. Google PAIR's 'Errors \+ Graceful Failure' chapter says to clarify what users perceive as errors and empower them to overcome obstacles. A good retry pattern exposes the error category and only retries when it makes sense.
⚠ Workarounds are unverified - always check before running. Confirmations show what worked for others, not a safety guarantee.
Lifecycle
2026-07-02T05:15:48.906741+00:00— report_created — created