chopratejas--headroom/REALIGNMENT/07-phase-E-cache-stabilization.md

Phase E — Phase 3 Cache Stabilization

Goal: Add the cache-stabilization surface that today is completely missing: tool array deterministic sort, recursive JSON Schema key sort, auto cache_control placement (Anthropic), prompt_cache_key auto-injection (OpenAI), volatile-content detector with customer warning (no rewrite), cache-bust drift telemetry. These are guide §8.5, §9.11, §6.2, §4.17 implementations and the "Phase 3" of the guide's implementation checklist.

Calendar: 1 week.

Shape: 6 PRs. Mostly parallel; E3 + E4 should land paired (per-mode policy).

---

PR-E1 — Tool array deterministic sort (Rust)

Branch: realign-E1-tool-array-sort Worktree: ~/claude-projects/headroom-worktrees/realign-E1-tool-array-sort Risk: LOW LOC: +200

Scope

Eliminate P3-28. Sort tools[] alphabetically by name on the way out. Idempotent: re-sorting an already-sorted array is a no-op. Implementation matches Python's existing _sort_tools_deterministically (headroom/proxy/handlers/anthropic.py:34-58) — same sort key, same output bytes (modulo serialization).

Files

Add:

• crates/headroom-proxy/src/compression/tool_def_normalize.rs:

  pub fn sort_tools_deterministically(tools: &mut Vec<&RawValue>) -> Result<()> {
      // Sort key: tool["name"] string, fallback to MD5(serialized) for unnamed tools.
      tools.sort_by_key(|t| {
          let parsed: serde_json::Value = serde_json::from_str(t.get()).unwrap_or_default();
          parsed.get("name").and_then(|v| v.as_str()).unwrap_or("").to_string()
      });
      Ok(())
  }
  

Modify:

• crates/headroom-proxy/src/compression/live_zone_anthropic.rs — call sort_tools_deterministically on the request body's tools array before forwarding (only on PAYG; gated by Phase F PR-F2).
• crates/headroom-proxy/src/compression/live_zone_openai.rs — same.
• crates/headroom-proxy/src/compression/live_zone_responses.rs — same.

Tests added:

• crates/headroom-proxy/tests/integration_tool_sort.rs::sort_alphabetic_by_name
• crates/headroom-proxy/tests/integration_tool_sort.rs::idempotent_resort_no_change
• crates/headroom-proxy/tests/integration_tool_sort.rs::byte_stable_across_runs

Acceptance criteria

• Tests pass.
• Output tools[] byte-equal between Rust and Python sort implementations.

Blocked by

PR-B2.

Blocks

PR-E2.

Rollback

git revert. Rust path matches client's tool order (subject to the cache-bust risk).

---

PR-E2 — Recursive JSON Schema key sort

Branch: realign-E2-schema-key-sort Worktree: ~/claude-projects/headroom-worktrees/realign-E2-schema-key-sort Risk: MEDIUM (recursive sort over tool schemas; risk of breaking schema semantics if there's an if/then/else or oneOf ordering invariant — there isn't, but verify) LOC: +300

Scope

Eliminate P3-29. Recursively sort JSON Schema object keys in every tool's input_schema. This includes nested properties, definitions, oneOf, anyOf, allOf, if/then/else, additionalProperties, etc.

Files

Modify:

• crates/headroom-proxy/src/compression/tool_def_normalize.rs — add sort_schema_keys_recursive. Walks every Object node; replaces with IndexMap rebuilt in alphabetic key order. Preserves Array order (JSON Schema arrays are ordered: prefixItems, oneOf alternatives, etc.).

Tests added:

• crates/headroom-proxy/tests/integration_schema_sort.rs::flat_schema_keys_sorted
• crates/headroom-proxy/tests/integration_schema_sort.rs::nested_properties_sorted
• crates/headroom-proxy/tests/integration_schema_sort.rs::oneof_array_order_preserved
• crates/headroom-proxy/tests/integration_schema_sort.rs::definitions_keys_sorted
• crates/headroom-proxy/tests/integration_schema_sort.rs::idempotent_resort

Acceptance criteria

• Tests pass.
• Snapshot test on a real production tool schema (e.g., Claude Code's Read tool) — pin the sorted bytes.

Blocked by

PR-E1.

Blocks

PR-E5.

Rollback

git revert. Schema keys reflect customer ordering.

---

PR-E3 — Auto cache_control breakpoint placement (Anthropic)

Branch: realign-E3-cache-control-auto-place Worktree: ~/claude-projects/headroom-worktrees/realign-E3-cache-control-auto-place Risk: MEDIUM-HIGH (auto-adds bytes to client request — only on PAYG) LOC: +400

Scope

Eliminate P3-31. When PAYG mode is detected (Phase F PR-F1) and the customer has not set any cache_control markers, auto-place up to 4 ephemeral markers at:

1. End of system prompt (1 marker)
2. End of tools[] (1 marker)
3. After the last stable conversation history boundary (1 marker; configurable threshold for "stable")
4. Before the latest user message (1 marker)

OAuth and subscription modes: never auto-place (could void scope).

Files

Add:

• crates/headroom-proxy/src/compression/cache_control.rs — pub fn auto_place_breakpoints(body: &mut serde_json::Value, auth_mode: AuthMode). Walks the structure; appends cache_control: {type: "ephemeral"} to the trailing block of system, tools, history, and current user message.

Modify:

• crates/headroom-proxy/src/compression/live_zone_anthropic.rs — call auto_place_breakpoints on PAYG only.

Tests added:

• crates/headroom-proxy/tests/integration_cache_control_auto.rs::payg_auto_places_4_markers
• crates/headroom-proxy/tests/integration_cache_control_auto.rs::oauth_no_auto_placement
• crates/headroom-proxy/tests/integration_cache_control_auto.rs::subscription_no_auto_placement
• crates/headroom-proxy/tests/integration_cache_control_auto.rs::customer_set_markers_respected_no_addition
• crates/headroom-proxy/tests/integration_cache_control_auto.rs::ttl_ordering_correct_1h_before_5m

Acceptance criteria

• Tests pass.
• Customer requests with existing markers are unmodified.
• A representative PAYG request gets 4 markers in the right positions.

Blocked by

PR-A4, PR-F1, PR-F2.

Blocks

None.

Rollback

git revert. Customers without their own cache_control markers don't get auto-placement; cache benefit smaller but correct.

---

PR-E4 — prompt_cache_key auto-injection (OpenAI)

Branch: realign-E4-prompt-cache-key-inject Worktree: ~/claude-projects/headroom-worktrees/realign-E4-prompt-cache-key-inject Risk: MEDIUM LOC: +250

Scope

Eliminate P3-30. For OpenAI Chat Completions and Responses requests on PAYG mode where the customer has not set prompt_cache_key, auto-inject one derived from a stable session hash. OAuth/subscription modes: never inject (the CLI may already populate this and Headroom must preserve byte-for-byte).

Files

Modify:

• crates/headroom-proxy/src/compression/live_zone_openai.rs — add inject_prompt_cache_key step.
• crates/headroom-proxy/src/compression/live_zone_responses.rs — same.

Add:

• crates/headroom-proxy/src/session.rs — pub fn derive_prompt_cache_key(session_id: &str, model: &str) -> String — returns {session_id}_{model_family} (deterministic per session+model).

Tests added:

• crates/headroom-proxy/tests/integration_prompt_cache_key.rs::payg_auto_injects_when_absent
• crates/headroom-proxy/tests/integration_prompt_cache_key.rs::customer_value_preserved
• crates/headroom-proxy/tests/integration_prompt_cache_key.rs::oauth_no_injection
• crates/headroom-proxy/tests/integration_prompt_cache_key.rs::subscription_no_injection
• crates/headroom-proxy/tests/integration_prompt_cache_key.rs::same_session_same_key_deterministic

Acceptance criteria

• Tests pass.

Blocked by

PR-F1, PR-F2.

Blocks

None.

Rollback

git revert. OpenAI cache routing less sticky on PAYG; functional.

---

PR-E5 — Volatile-content detector with customer warning (no rewrite)

Branch: realign-E5-volatile-detector Worktree: ~/claude-projects/headroom-worktrees/realign-E5-volatile-detector Risk: LOW LOC: +400

Scope

Eliminate P3-32. Detect dynamic content in the early prompt (timestamps, UUIDs, JWT tokens, build hashes, randomized IDs) and surface to the customer via a log line and a Prometheus metric. Do not rewrite. This is what Python's cache_aligner.py was trying to do correctly (the rewrite path is gone in Phase A PR-A2).

Files

Add:

• crates/headroom-core/src/transforms/volatile_detector.rs:

  pub struct VolatileDetector { /* compiled regex set */ }
  
  impl VolatileDetector {
      pub fn scan(&self, content: &str) -> Vec<VolatileFinding>;
  }
  
  pub struct VolatileFinding {
      pub kind: VolatileKind,  // Timestamp | Uuid | Jwt | BuildHash | ...
      pub byte_offset: usize,
      pub matched: String,
      pub recommendation: String,  // "Move to metadata"
  }
  

  Patterns:
  • ISO 8601 timestamp regex
  • UUID v4 regex
  • JWT shape (eyJ...)
  • Long hex strings >=32 chars (build hashes)
  • Unix epoch timestamps within an order of magnitude of now

Modify:

• crates/headroom-proxy/src/compression/live_zone_anthropic.rs — run scanner on system prompt; if findings, log warning and increment metric.
• crates/headroom-proxy/src/compression/live_zone_openai.rs — same on instructions field.
• crates/headroom-proxy/src/compression/live_zone_responses.rs — same.

Tests added:

• crates/headroom-core/tests/volatile_detector.rs::detects_iso_8601_timestamp
• crates/headroom-core/tests/volatile_detector.rs::detects_uuid_v4
• crates/headroom-core/tests/volatile_detector.rs::detects_jwt_shape
• crates/headroom-core/tests/volatile_detector.rs::detects_build_hash
• crates/headroom-core/tests/volatile_detector.rs::no_false_positives_on_normal_prose
• crates/headroom-proxy/tests/integration_volatile.rs::warning_logged_on_volatile_system_prompt
• crates/headroom-proxy/tests/integration_volatile.rs::system_prompt_bytes_unchanged

Acceptance criteria

• Tests pass.
• Detector runs in <1ms on a 4KB system prompt (don't slow the request path).

Blocked by

PR-E2.

Blocks

None.

Rollback

git revert. Detector loses; no functional regression.

---

PR-E6 — Cache-bust drift detector telemetry

Branch: realign-E6-cache-bust-detector Worktree: ~/claude-projects/headroom-worktrees/realign-E6-cache-bust-detector Risk: LOW LOC: +500

Scope

Eliminate P3-35. Hash the prefix (system + tools + first N stable messages) of every request. Track per-session prefix hashes. When the prefix hash changes between turns, increment a counter and log a prefix_drift event with which subsystem mutated (likely none after Phase A — but if it happens, we want to know).

Files

Add:

• crates/headroom-proxy/src/observability/prefix_drift.rs:

  pub struct PrefixDriftDetector {
      // Keyed by session_id; stores last-seen prefix hash + timestamp.
      cache: Cache<SessionId, (PrefixHash, Instant)>,
  }
  
  impl PrefixDriftDetector {
      pub fn check(&self, session_id: &str, body: &serde_json::Value) -> DriftCheck;
  }
  
  pub enum DriftCheck {
      FirstSeen,
      Stable,
      Drifted { previous_hash: PrefixHash, new_hash: PrefixHash, age: Duration },
  }
  

Modify:

• crates/headroom-proxy/src/observability/prometheus.rs — add prefix_drift_detected_total{provider, model} counter.

Tests added:

• crates/headroom-proxy/tests/integration_prefix_drift.rs::stable_prefix_no_drift
• crates/headroom-proxy/tests/integration_prefix_drift.rs::system_change_detected_as_drift
• crates/headroom-proxy/tests/integration_prefix_drift.rs::tools_reorder_detected

Acceptance criteria

• Tests pass.
• A canary request that mutates the system prompt mid-session triggers the counter.

Blocked by

PR-B2.

Blocks

None.

Rollback

git revert. Loses observability; no functional regression.

---

Phase E acceptance summary

After all 6 PRs land:

• ✅ Tools alphabetically sorted (deterministic, idempotent)
• ✅ JSON Schema keys recursively sorted
• ✅ cache_control auto-placement on PAYG (4 markers)
• ✅ prompt_cache_key auto-injection on PAYG (OpenAI)
• ✅ Volatile-content detector + customer warning (no rewrite)
• ✅ Cache-bust drift telemetry per session

Phase E retires P3-28 through P3-32, P3-35.