anthropic

name	anthropic
description	Anthropic Claude Pro/Max OAuth compatibility workflow for this repo. Use when debugging Anthropic OAuth failures, misleading extra-usage errors, Pi request shaping, prompt fingerprinting, or deciding between hook-based fixes and deeper provider overrides.
compatibility	Intended for the pi-anthropic-auth repository and Pi Anthropic OAuth investigations.

Anthropic OAuth Compatibility

Use When

• Anthropic OAuth requests fail with You're out of extra usage.
• Pi Anthropic OAuth works for login but fails for actual requests.
• You need to compare Pi, OpenCode, and opencode-anthropic-auth behavior.
• You need to decide whether a fix belongs in before_provider_request, the streamSimple transport wrapper, or a deeper override.

Core Lessons

1. Treat Anthropic's You're out of extra usage. error as a possible disguised request rejection, not only a billing problem.
2. Prefer the thinnest fix that works.
3. Preserve Pi's built-in Anthropic behavior by default.
4. Prefer request shaping before prompt rewriting.
5. Avoid streamSimple unless hooks are clearly insufficient — they are insufficient for compaction and background-agent calls, which is why this repo wraps the transport (Issue #18).

Repo-Specific Findings

Confirmed Pi upstream behavior

• Pi already handles Claude Code OAuth headers, Claude Code identity injection, native Anthropic OAuth login, and tool-name normalization.
• Pi auth storage already refreshes OAuth tokens under a lock.

Confirmed local fixes

• Refresh fallback preserves the previous refresh token when Anthropic omits refresh_token.
• OAuth Anthropic payload shaping prepends an x-anthropic-billing-header system block.
• The billing block must not add cache_control, or Anthropic can reject the request for exceeding the cache-control block limit.
• Assistant message ordering must be normalized when Pi serializes [tool_use..., text] for Anthropic.
• Pi's default system prompt can act as an Anthropic fingerprint and trigger disguised rejection errors.
• Shaping runs in a thin streamSimple transport wrapper (delegating to Pi's streamSimpleAnthropic), so it applies to every OAuth call path — main loop, completeSimple compaction, and agentLoop background agents — gated on the sk-ant-oat token.

Fast Debugging Workflow

1. Reproduce with the real pi CLI

Use the actual CLI rather than only unit tests:

pi \
  --model anthropic/claude-haiku-4-5 \
  --no-session \
  --tools read,grep,find,ls \
  -e /Users/chris/development/pi/pi-anthropic-auth/src/index.ts \
  -p "How many lines are in @AGENTS.md ?"

This gives the shortest reliable feedback loop for live Anthropic OAuth behavior. Prefer the latest Haiku alias for fast repros unless the bug appears model-specific.

If an installed copy of this extension is listed in ~/.pi/agent/settings.json, -e <local path> loads the local copy in addition to the installed one, so shaping appears to run twice. Add --no-extensions to the repro command to load only the -e copy when verifying local changes.

This workflow has already been used successfully in this repo to validate:

1. simple prompts
2. tool use
3. multi-turn continuation
4. structured output
5. expired-token refresh

2. Distinguish the failure class

• If a minimal custom --system-prompt succeeds but the default Pi prompt fails, suspect prompt fingerprinting.
• If failures happen only after tool use or multi-turn flows, inspect serialized Anthropic message ordering.
• Use PI_ANTHROPIC_AUTH_DEBUG=tool-use to log only tool-using Anthropic OAuth requests, or PI_ANTHROPIC_AUTH_DEBUG=all to log every shaped OAuth request.
• If validation errors mention block counts or payload shape, inspect system[], cache_control, and messages ordering.

Implementation Guidance

Shape in the streamSimple transport wrapper

All request shaping runs in the transport wrapper (src/oauth-transport.ts), which delegates to Pi's streamSimpleAnthropic and injects an onPayload step:

• billing-header injection
• system[] block ordering
• cache-control adjustments
• assistant message ordering normalization
• system prompt de-fingerprinting (replaces Pi's default preamble with a minimal neutral prompt)

Gate on the sk-ant-oat access-token prefix (options.apiKey), the same signal Pi uses internally. This covers every OAuth call path, including compaction and background agents.

Why not before_provider_request or before_agent_start

before_provider_request only fires for the interactive agent loop, so it never reaches compaction or background-agent calls (Issue #18).

before_agent_start has no provider or model context, and there is no reliable way to gate provider-specific logic there:

• model_select does not fire for the initial model at startup (Pi assigns it directly to agent.state.model without calling setModel).
• The event itself does not expose which provider is active.

Avoid by default

• wholesale OpenCode debranding logic
• mcp_ tool prefix transport hacks
• reimplementing Pi's Anthropic transport (the wrapper delegates to streamSimpleAnthropic instead)

Useful References

• AGENTS.md
• docs/plans/minimal-anthropic-override.md
• docs/plans/gap-analysis-and-next-steps.md
• src/index.ts
• src/oauth-transport.ts
• src/request-shaping.ts
• src/system-prompt-shaping.ts
• src/anthropic-oauth.ts
• test/pi-anthropic-ordering-experiment.test.ts
• test/system-prompt-shaping.test.ts

Decision Rule

When debugging a new Anthropic OAuth failure in this repo:

1. Reproduce with pi -p ... -e ....
2. Decide whether the failure is prompt fingerprinting, request shape, or transport.
3. Fix it in the shallowest seam that can solve it — but remember before_provider_request covers only the interactive loop, so cross-call-path fixes belong in the transport wrapper.