chopratejas--headroom/REALIGNMENT/08-phase-F-auth-mode.md

Phase F — Auth-Mode Policy Gates

Goal: Make auth mode a first-class policy axis. Detect (PAYG / OAuth / subscription) at request entry; gate compression behavior, header injection, and TOIN aggregation per mode. Stealth mode for subscription CLIs.

Calendar: 1 week.

Shape: 4 PRs. F1 first; F2 + F3 + F4 parallel after.

Reference: ~/.claude/projects/-Users-tchopra-claude-projects-headroom/memory/project_auth_mode_compression_nuances.md.

---

PR-F1 — classify_auth_mode helper

Branch: realign-F1-classify-auth-mode Worktree: ~/claude-projects/headroom-worktrees/realign-F1-classify-auth-mode Risk: LOW LOC: +500

Scope

Single helper called at request entry returning AuthMode = Payg | OAuth | Subscription. Pure-function classification from headers (Authorization shape, OpenAI-Beta, anthropic-beta) and User-Agent prefix.

Files

Add:

• crates/headroom-core/src/auth_mode.rs:

  #[derive(Debug, Clone, Copy, PartialEq, Eq, Hash)]
  pub enum AuthMode { Payg, OAuth, Subscription }
  
  pub fn classify(headers: &http::HeaderMap) -> AuthMode {
      let ua = headers.get("user-agent").and_then(|h| h.to_str().ok()).unwrap_or("").to_lowercase();
      const SUBSCRIPTION_UA_PREFIXES: &[&str] = &[
          "claude-cli/", "claude-code/", "codex-cli/", "cursor/",
          "claude-vscode/", "github-copilot/", "anthropic-cli/", "antigravity/",
      ];
      if SUBSCRIPTION_UA_PREFIXES.iter().any(|p| ua.contains(p)) {
          return AuthMode::Subscription;
      }
  
      let auth = headers.get("authorization").and_then(|h| h.to_str().ok()).unwrap_or("");
      if auth.starts_with("Bearer ") {
          let token = &auth[7..];
          if token.starts_with("sk-ant-api") || token.starts_with("sk-") {
              return AuthMode::Payg;
          }
          if token.starts_with("sk-ant-oat-") || token.split('.').count() >= 3 {
              // sk-ant-oat-* (Claude Pro OAuth) or JWT (Codex/Cursor OAuth)
              return AuthMode::OAuth;
          }
      }
  
      // Bedrock / Vertex (no Authorization header from client; signed downstream)
      if !auth.is_empty() == false
         && headers.get("x-api-key").is_none()
         && headers.get("x-goog-api-key").is_none()
      {
          return AuthMode::OAuth;
      }
  
      // x-api-key present (Anthropic API key style)
      if headers.contains_key("x-api-key") {
          return AuthMode::Payg;
      }
  
      AuthMode::Payg  // default
  }
  

Add (Python):

• headroom/proxy/auth_mode.py — Python port of the same logic. Used in Python paths until Phase H deletes them.

Modify:

• crates/headroom-core/src/lib.rs — pub mod auth_mode;.
• crates/headroom-proxy/src/proxy.rs — call classify at request entry; store in request extensions for downstream handlers.
• headroom/proxy/handlers/anthropic.py — call Python classify_auth_mode(headers) at request entry.
• headroom/proxy/handlers/openai.py — same.

Tests added:

• crates/headroom-core/tests/auth_mode.rs::api_key_classified_payg
• crates/headroom-core/tests/auth_mode.rs::oauth_jwt_classified_oauth
• crates/headroom-core/tests/auth_mode.rs::oauth_sk_ant_oat_classified_oauth
• crates/headroom-core/tests/auth_mode.rs::claude_code_ua_classified_subscription
• crates/headroom-core/tests/auth_mode.rs::cursor_ua_classified_subscription
• crates/headroom-core/tests/auth_mode.rs::no_auth_no_user_agent_default_payg
• crates/headroom-core/tests/auth_mode.rs::bedrock_no_auth_classified_oauth
• Python equivalents in tests/test_auth_mode.py.

Acceptance criteria

• Tests pass.
• Detection runs in <10us per call.
• Documented in docs/auth-modes.md with the detection rules and how to extend.

Blocked by

None.

Blocks

PR-F2, PR-F3, PR-F4.

Rollback

git revert. All requests treated as PAYG (current behavior).

---

PR-F2 — Per-mode compression policy gates

Branch: realign-F2-per-mode-policy Worktree: ~/claude-projects/headroom-worktrees/realign-F2-per-mode-policy Risk: MEDIUM-HIGH (changes compression behavior per request) LOC: +600

Scope

Wire AuthMode into every compression decision per the policy matrix in 02-architecture.md §2.4. PAYG = aggressive (current default). OAuth = passthrough-prefer (no auto-cache_control, no auto-prompt_cache_key, no lossy compressors). Subscription = stealth (everything OAuth does + preserve accept-encoding, never strip; never inject X-Headroom-*; never mutate User-Agent).

Files

Modify:

• crates/headroom-proxy/src/compression/live_zone_anthropic.rs — gate auto_place_breakpoints on auth_mode == Payg.
• crates/headroom-proxy/src/compression/live_zone_openai.rs — gate inject_prompt_cache_key on auth_mode == Payg.
• crates/headroom-proxy/src/compression/live_zone.rs — gate lossy compressors (Kompress text) on auth_mode == Payg. OAuth and Subscription get lossless-only compression.
• crates/headroom-proxy/src/headers.rs:103-117 — add_x_forwarded_headers becomes add_x_forwarded_headers_if(auth_mode). Skip on Subscription.
• crates/headroom-proxy/src/proxy.rs — accept-encoding strip becomes conditional on auth_mode != Subscription.
• headroom/proxy/handlers/anthropic.py — gate Python compression decisions identically.
• headroom/proxy/handlers/openai.py — same.

Tests added:

• crates/headroom-proxy/tests/integration_authmode_policy.rs::payg_aggressive_compression
• crates/headroom-proxy/tests/integration_authmode_policy.rs::oauth_no_auto_cache_control
• crates/headroom-proxy/tests/integration_authmode_policy.rs::oauth_no_auto_prompt_cache_key
• crates/headroom-proxy/tests/integration_authmode_policy.rs::oauth_lossless_only
• crates/headroom-proxy/tests/integration_authmode_policy.rs::subscription_no_x_forwarded
• crates/headroom-proxy/tests/integration_authmode_policy.rs::subscription_preserves_accept_encoding
• crates/headroom-proxy/tests/integration_authmode_policy.rs::subscription_lossless_only

Acceptance criteria

• Tests pass.
• Manual smoke test: a real Claude Code session through the proxy produces no X-Forwarded-* upstream and preserves accept-encoding.

Blocked by

PR-F1, PR-E3, PR-E4.

Blocks

None.

Rollback

git revert. All requests treated as PAYG. No functional regression for PAYG users; OAuth/Subscription users may see scope-rejection or revocation increase.

---

PR-F3 — TOIN per-tenant aggregation key

Branch: realign-F3-toin-per-tenant Worktree: ~/claude-projects/headroom-worktrees/realign-F3-toin-per-tenant Risk: MEDIUM LOC: -200 / +400

Scope

Eliminate P5-56. Extend TOIN's aggregation key from structure_hash to (auth_mode, model_family, structure_hash). Storage key prefix updated; in-memory dicts re-keyed. Existing observations from before this PR are preserved under a legacy/ prefix and deprecated over the next 30 days.

Files

Modify:

• headroom/telemetry/toin.py:103 — Pattern adds auth_mode: str = "unknown", model_family: str = "unknown". (Already covered by Phase B PR-B5; this PR ensures the wiring lands.)
• headroom/telemetry/toin.py:477, 496, 727, 729, 1248, 1256 — change aggregation key to tuple.
• headroom/telemetry/toin.py — migration helper that walks the legacy structure_hash-only store and copies entries under ("unknown", "unknown", structure_hash) for graceful degrade.
• headroom/telemetry/toin.py — bumping aggregation key invalidates earlier recommendations; re-publish via the deploy CLI.
• headroom/subscription/tracker.py:166 — replace _current_token: str (raw OAuth bearer storage) with _current_token_id: str (a one-way hash + last-4 chars for debugging). Polling code adapts to use the actual Authorization header per request rather than the stored copy.

Tests added:

• tests/test_toin_per_tenant.py::test_aggregation_key_includes_auth_mode_model
• tests/test_toin_per_tenant.py::test_legacy_observations_preserved_under_unknown
• tests/test_toin_per_tenant.py::test_publish_per_auth_mode_writes_separate_recommendations
• tests/test_subscription_tracker_token_hardening.py::test_raw_token_not_stored_in_memory

Acceptance criteria

• Tests pass.
• Recommendations file becomes structured recommendations.toml with sections per (auth_mode, model_family).
• The subscription tracker token-leak risk closed.

Blocked by

PR-B5, PR-F1.

Blocks

None.

Rollback

git revert. TOIN reverts to global aggregation. No functional break.

---

PR-F4 — X-Forwarded-* conditional in Rust path

Branch: realign-F4-x-forwarded-conditional Worktree: ~/claude-projects/headroom-worktrees/realign-F4-x-forwarded-conditional Risk: LOW LOC: +100

Scope

Eliminate P5-53. The Rust proxy currently always adds X-Forwarded-For, X-Forwarded-Proto, X-Forwarded-Host, X-Request-Id to upstream-bound requests. Make this conditional: PAYG → add; OAuth → add; Subscription → skip (fingerprint risk).

Files

Modify:

• crates/headroom-proxy/src/headers.rs:103-117 — add_x_forwarded_headers takes an AuthMode parameter; no-ops on Subscription.

Tests added:

• crates/headroom-proxy/tests/integration_x_forwarded_authmode.rs::payg_adds_xfwd
• crates/headroom-proxy/tests/integration_x_forwarded_authmode.rs::oauth_adds_xfwd
• crates/headroom-proxy/tests/integration_x_forwarded_authmode.rs::subscription_no_xfwd

Acceptance criteria

• Tests pass.

Blocked by

PR-F1.

Blocks

None.

Rollback

git revert. Headers always added. Mild fingerprint regression for Subscription users.

---

Phase F acceptance summary

After all 4 PRs land:

• ✅ classify_auth_mode helper detects PAYG / OAuth / Subscription
• ✅ Per-mode compression policy gates (auto-cache_control, prompt_cache_key, lossy compressors)
• ✅ TOIN aggregation key per (auth_mode, model_family, structure_hash)
• ✅ Subscription tracker doesn't store raw OAuth bearer
• ✅ X-Forwarded-* skipped on Subscription mode
• ✅ accept-encoding preserved on Subscription mode

Phase F retires P5-52, P5-53, P5-54, P5-55, P5-56.

After Phase F, fingerprint risk for Subscription CLI users is dramatically reduced.