What this error means
HTTP 400: This model does not support assistant message prefill. The conversation must end with a user message. is a LiteLLM failure pattern reported for developers trying to fix litellm streaming fallback sending unsupported assistant prefill to claude models causing 400 error. Based on the imported evidence, treat this as a tool-specific troubleshooting page rather than a generic API error.
Why this happens
Filed 2026-05-14. Detailed bug report with repro code. Affects LiteLLM Router with streaming fallbacks to Claude Sonnet 4.6/Opus 4.7. The escape hatches (disable_fallbacks, CustomLogger hooks) don't work. Users resort to monkey-patching.
Common causes
- When a streaming request fails mid-stream, LiteLLM's fallback mechanism unconditionally appends an assistant prefill block. Claude Sonnet 4.6/Opus 4.7 don't support this, so fallback silently fails with 400. Users see the wrong error instead of the real upstream failure.
- Filed 2026-05-14. Detailed bug report with repro code. Affects LiteLLM Router with streaming fallbacks to Claude Sonnet 4.6/Opus 4.7. The escape hatches (disable_fallbacks, CustomLogger hooks) don't work. Users resort to monkey-patching.
Quick fixes
- Confirm the exact error signature matches
HTTP 400: This model does not support assistant message prefill. The conversation must end with a user message.. - Check the LiteLLM account, local tool state, and provider configuration involved in the failing workflow.
- Compare the failing environment with a known working setup, then change one configuration value at a time.
Platform/tool-specific checks
- Verify the command, editor, extension, or API client that produced the error.
- Compare local settings with CI, deployment, or editor-level settings when the error appears in only one environment.
- Avoid deleting credentials, local model data, or project settings until the failing scope is clear.
Step-by-step troubleshooting
- Capture the exact error message and the command, editor action, or request that triggered it.
- Check whether the failure is account/auth, quota/rate, model/provider, local runtime, or deployment configuration.
- Review the source evidence below and compare it with your environment.
- Apply one change at a time and rerun the smallest failing action.
- Keep the working fix documented for the team or deployment environment.
How to prevent it
- Keep provider/tool configuration documented.
- Record non-secret diagnostics such as tool version, provider name, model name, and command path.
- Add a lightweight check before CI or production workflows depend on the tool.