diff --git a/e2e/wrap/run.py b/e2e/wrap/run.py
index 2a6c93544..14b931fd2 100644
--- a/e2e/wrap/run.py
+++ b/e2e/wrap/run.py
@@ -355,6 +355,11 @@ def start_openclaw_gateway(env: dict[str, str], cwd: Path) -> subprocess.Popen[s
     )
 
 
+def stop_openclaw_gateway(env: dict[str, str], cwd: Path) -> None:
+    log("Stopping OpenClaw gateway after e2e verification")
+    run(["openclaw", "gateway", "stop"], env=env, cwd=cwd, timeout=60)
+
+
 def verify_installs() -> None:
     log("Verifying installed packages and binaries")
     for tool in ("headroom", "codex", "aider", "openclaw"):
@@ -617,6 +622,7 @@ def verify_openclaw_wrap(
     finally:
         if gateway_proc is not None:
             stop_process(gateway_proc)
+        stop_openclaw_gateway(base_env, project_dir)
 
 
 def main() -> None:
diff --git a/headroom/cli/wrap.py b/headroom/cli/wrap.py
index e37a20fed..7c260850c 100644
--- a/headroom/cli/wrap.py
+++ b/headroom/cli/wrap.py
@@ -1132,6 +1132,24 @@ def openclaw(
     elif not local_source_mode and skip_build:
         click.echo("  Skipping build: npm install mode does not build local source.")
 
+    effective_python_path = python_path
+    if effective_python_path is None and not no_auto_start and sys.executable:
+        effective_python_path = sys.executable
+
+    existing_entry = _read_openclaw_config_value(openclaw_bin, "plugins.entries.headroom")
+    entry = _build_openclaw_plugin_entry(
+        existing_entry=existing_entry,
+        proxy_port=proxy_port,
+        startup_timeout_ms=startup_timeout_ms,
+        python_path=effective_python_path,
+        no_auto_start=no_auto_start,
+        gateway_provider_ids=gateway_provider_ids,
+        enabled=True,
+    )
+
+    click.echo("  Writing plugin configuration...")
+    _write_openclaw_plugin_entry(openclaw_bin, entry)
+
     install_cmd = [
         openclaw_bin,
         "plugins",
@@ -1184,19 +1202,6 @@ def openclaw(
     elif verbose and install_result.stdout.strip():
         click.echo(install_result.stdout.strip())
 
-    existing_entry = _read_openclaw_config_value(openclaw_bin, "plugins.entries.headroom")
-    entry = _build_openclaw_plugin_entry(
-        existing_entry=existing_entry,
-        proxy_port=proxy_port,
-        startup_timeout_ms=startup_timeout_ms,
-        python_path=python_path,
-        no_auto_start=no_auto_start,
-        gateway_provider_ids=gateway_provider_ids,
-        enabled=True,
-    )
-
-    click.echo("  Writing plugin configuration...")
-    _write_openclaw_plugin_entry(openclaw_bin, entry)
     _set_openclaw_context_engine_slot(openclaw_bin, "headroom")
     _run_checked(
         [openclaw_bin, "config", "validate"],
diff --git a/plugins/openclaw/test/engine.test.ts b/plugins/openclaw/test/engine.test.ts
index 8dc3acba4..bd8005deb 100644
--- a/plugins/openclaw/test/engine.test.ts
+++ b/plugins/openclaw/test/engine.test.ts
@@ -1,300 +1,101 @@
-/**
- * Integration tests for HeadroomContextEngine.
- *
- * Tests the full flow: proxy management, AgentMessage conversion,
- * compression via proxy, and round-trip back to AgentMessage.
- *
- * Requires: Python 3 + headroom-ai[proxy] installed
- * Run: HEADROOM_INTEGRATION=1 npx vitest run test/engine.test.ts
- */
-import { describe, it, expect, beforeAll, afterAll, vi, afterEach } from "vitest";
-import { HeadroomContextEngine } from "../src/engine.js";
-import { agentToOpenAI, openAIToAgent } from "../src/convert.js";
-import { ProxyManager } from "../src/proxy-manager.js";
+import { afterEach, describe, expect, it, vi } from "vitest";
 
-const RUN = process.env.HEADROOM_INTEGRATION === "1";
-const PROXY_URL = process.env.HEADROOM_PROXY_URL ?? "http://127.0.0.1:8787";
+const mocked = vi.hoisted(() => ({
+  start: vi.fn(async () => "http://127.0.0.1:8787"),
+  stop: vi.fn(async () => undefined),
+  logger: {
+    debug: vi.fn(),
+    error: vi.fn(),
+    info: vi.fn(),
+    warn: vi.fn(),
+  },
+}));
+
+vi.mock("headroom-ai", () => ({
+  compress: vi.fn(),
+}));
+
+vi.mock("../src/proxy-manager.js", () => ({
+  ProxyManager: class {
+    start = mocked.start;
+    stop = mocked.stop;
+  },
+  defaultLogger: mocked.logger,
+}));
+
+import { HeadroomContextEngine } from "../src/engine.js";
 
 afterEach(() => {
-  vi.restoreAllMocks();
+  mocked.start.mockReset();
+  mocked.start.mockResolvedValue("http://127.0.0.1:8787");
+  mocked.stop.mockClear();
+  mocked.logger.debug.mockClear();
+  mocked.logger.error.mockClear();
+  mocked.logger.info.mockClear();
+  mocked.logger.warn.mockClear();
 });
 
-// Proxy probing and ProxyManager.start tests live in proxy-manager.test.ts
-
-describe("AgentMessage conversion", () => {
-  it("converts user message", () => {
-    const agent = [{ role: "user", content: "hello", timestamp: Date.now() }];
-    const openai = agentToOpenAI(agent);
-    expect(openai).toHaveLength(1);
-    expect(openai[0]).toMatchObject({ role: "user", content: "hello" });
-  });
-
-  it("converts assistant with tool_use blocks", () => {
-    const agent = [
-      {
-        role: "assistant",
-        content: [
-          { type: "text", text: "Let me search" },
-          { type: "tool_use", id: "tu_1", name: "search", input: { q: "test" } },
-        ],
-        timestamp: Date.now(),
-      },
-    ];
-    const openai = agentToOpenAI(agent);
-    expect(openai[0].role).toBe("assistant");
-    expect(openai[0].content).toBe("Let me search");
-    expect(openai[0].tool_calls).toHaveLength(1);
-    expect(openai[0].tool_calls![0].function.name).toBe("search");
-  });
-
-  it("converts assistant with toolCall blocks", () => {
-    const agent = [
-      {
-        role: "assistant",
-        content: [
-          { type: "text", text: "Let me search" },
-          { type: "toolCall", id: "call_1|fc_1", name: "search", arguments: { q: "test" } },
-        ],
-        timestamp: Date.now(),
-      },
-    ];
-    const openai = agentToOpenAI(agent);
-    expect(openai[0].role).toBe("assistant");
-    expect(openai[0].content).toBe("Let me search");
-    expect(openai[0].tool_calls).toHaveLength(1);
-    expect(openai[0].tool_calls![0].id).toBe("call_1|fc_1");
-    expect(openai[0].tool_calls![0].function.name).toBe("search");
-  });
-
-  it("converts toolResult message", () => {
-    const agent = [
-      {
-        role: "toolResult",
-        content: '{"results": [1, 2, 3]}',
-        tool_use_id: "tu_1",
-        timestamp: Date.now(),
-      },
-    ];
-    const openai = agentToOpenAI(agent);
-    expect(openai[0].role).toBe("tool");
-    expect(openai[0].content).toBe('{"results": [1, 2, 3]}');
-    expect(openai[0].tool_call_id).toBe("tu_1");
-  });
-
-  it("round-trips user message", () => {
-    const original = [{ role: "user", content: "hello", timestamp: Date.now() }];
-    const openai = agentToOpenAI(original);
-    const back = openAIToAgent(openai);
-    expect(back[0].role).toBe("user");
-    expect(back[0].content).toBe("hello");
-  });
-
-  it("round-trips assistant text-only (content always array)", () => {
-    const original = [
-      {
-        role: "assistant",
-        content: [{ type: "text", text: "Hello there!" }],
-        timestamp: Date.now(),
-      },
-    ];
-    const openai = agentToOpenAI(original);
-    const back = openAIToAgent(openai);
-    expect(back[0].role).toBe("assistant");
-    // OpenClaw requires content to ALWAYS be an array for assistant messages
-    const content = back[0].content;
-    expect(Array.isArray(content)).toBe(true);
-    expect(content[0]).toEqual({ type: "text", text: "Hello there!" });
-  });
-
-  it("round-trips assistant with tool calls", () => {
-    const original = [
-      {
-        role: "assistant",
-        content: [
-          { type: "text", text: "Searching..." },
-          { type: "toolCall", id: "call_1|fc_1", name: "search", arguments: { q: "test" } },
-        ],
-        timestamp: Date.now(),
-      },
-    ];
-    const openai = agentToOpenAI(original);
-    const back = openAIToAgent(openai);
-    expect(back[0].role).toBe("assistant");
-    const content = back[0].content;
-    expect(Array.isArray(content)).toBe(true);
-    expect(content).toContainEqual(expect.objectContaining({ type: "text", text: "Searching..." }));
-    expect(content).toContainEqual(
-      expect.objectContaining({ type: "toolCall", id: "call_1|fc_1", name: "search" }),
-    );
-  });
-
-  it("round-trips toolResult", () => {
-    const original = [
-      {
-        role: "toolResult",
-        content: '{"data": true}',
-        tool_use_id: "tu_1",
-        timestamp: Date.now(),
-      },
-    ];
-    const openai = agentToOpenAI(original);
-    const back = openAIToAgent(openai);
-    expect(back[0].role).toBe("toolResult");
-    expect(back[0].content).toEqual([{ type: "text", text: '{"data": true}' }]);
-    expect(back[0].tool_use_id).toBe("tu_1");
-  });
-});
-
-describe("HeadroomContextEngine startup behavior", () => {
-  it("bootstrap schedules proxy startup without blocking on it", async () => {
-    const start = vi.fn(
-      () => new Promise<string>((resolve) => setTimeout(() => resolve("http://127.0.0.1:8787"), 50)),
-    );
-    vi.spyOn(ProxyManager.prototype, "start").mockImplementation(start);
-
+describe("HeadroomContextEngine proxy startup helpers", () => {
+  it("bootstraps by scheduling proxy startup when enabled", async () => {
     const engine = new HeadroomContextEngine();
-    const result = await engine.bootstrap({
-      sessionId: "test-session",
-      sessionFile: "/tmp/test-session.jsonl",
-    });
 
-    expect(result).toEqual({ bootstrapped: true, reason: "proxy startup scheduled" });
-    expect(start).toHaveBeenCalledTimes(1);
-    expect(engine.getProxyUrl()).toBeNull();
+    await expect(
+      engine.bootstrap({
+        sessionId: "session-1",
+        sessionFile: "session.jsonl",
+      }),
+    ).resolves.toEqual({
+      bootstrapped: true,
+      reason: "proxy startup scheduled",
+    });
+    expect(mocked.start).toHaveBeenCalledTimes(1);
   });
 
-  it("assemble returns original messages while proxy startup is still pending", async () => {
-    const start = vi.fn(
-      () => new Promise<string>((resolve) => setTimeout(() => resolve("http://127.0.0.1:8787"), 50)),
-    );
-    vi.spyOn(ProxyManager.prototype, "start").mockImplementation(start);
-
+  it("removes unsubscribed proxy listeners before notifying readiness", async () => {
     const engine = new HeadroomContextEngine();
-    const messages = [{ role: "user", content: "hello", timestamp: Date.now() }];
+    const first = vi.fn();
+    const second = vi.fn();
 
-    const result = await engine.assemble({
-      sessionId: "test-session",
+    const unsubscribeFirst = engine.onProxyReady(first);
+    engine.onProxyReady(second);
+    unsubscribeFirst();
+
+    engine.ensureProxyStarted();
+    await engine.ensureProxyUrl();
+
+    expect(first).not.toHaveBeenCalled();
+    expect(second).toHaveBeenCalledWith("http://127.0.0.1:8787");
+  });
+
+  it("returns the existing proxy URL without starting again", async () => {
+    const engine = new HeadroomContextEngine();
+
+    (engine as { proxyUrl: string | null }).proxyUrl = "http://127.0.0.1:8787";
+
+    await expect(engine.ensureProxyUrl()).resolves.toBe("http://127.0.0.1:8787");
+    expect(mocked.start).not.toHaveBeenCalled();
+  });
+
+  it("throws when proxy startup is disabled", async () => {
+    const engine = new HeadroomContextEngine({ enabled: false });
+
+    await expect(engine.ensureProxyUrl()).rejects.toThrow("Headroom proxy startup is disabled");
+    expect(mocked.start).not.toHaveBeenCalled();
+  });
+
+  it("schedules startup and returns original messages when assembling before proxy readiness", async () => {
+    const engine = new HeadroomContextEngine();
+    const messages = [{ role: "user", content: "hello" }];
+
+    await expect(
+      engine.assemble({
+        sessionId: "session-1",
+        messages,
+      }),
+    ).resolves.toEqual({
       messages,
-      model: "claude-sonnet-4-5",
+      estimatedTokens: 0,
     });
-
-    expect(result).toEqual({ messages, estimatedTokens: 0 });
-    expect(start).toHaveBeenCalledTimes(1);
+    expect(mocked.start).toHaveBeenCalledTimes(1);
   });
 });
-
-if (RUN) {
-  describe("ProxyManager", () => {
-    it("connects to configured proxy URL", { timeout: 30000 }, async () => {
-      const manager = new ProxyManager({ proxyUrl: PROXY_URL });
-      try {
-        const url = await manager.start();
-        expect(url).toMatch(/^http:\/\/(127\.0\.0\.1|localhost):\d+$/);
-
-        // Verify health
-        const resp = await fetch(`${url}/health`);
-        expect(resp.ok).toBe(true);
-      } finally {
-        await manager.stop();
-      }
-    });
-  });
-
-  describe("HeadroomContextEngine", () => {
-    let engine: HeadroomContextEngine;
-
-    beforeAll(async () => {
-      engine = new HeadroomContextEngine({ proxyUrl: PROXY_URL });
-      await engine.bootstrap({
-        sessionId: "test-session",
-        sessionFile: "/tmp/test-session.jsonl",
-      });
-    }, 30000);
-
-    afterAll(async () => {
-      await engine.dispose();
-    });
-
-    it("assemble() compresses tool outputs", { timeout: 15000 }, async () => {
-    // Simulate an OpenClaw agent conversation with large tool result
-    const serverData = Array.from({ length: 100 }, (_, i) => ({
-      id: i + 1,
-      name: `server-${i + 1}`,
-      status: i % 15 === 0 ? "critical" : i % 5 === 0 ? "warning" : "healthy",
-      cpu: Math.round(Math.random() * 100),
-      memory: Math.round(Math.random() * 100),
-      region: ["us-east-1", "eu-west-1", "ap-southeast-1"][i % 3],
-      description: `Production server ${i + 1} running service-${["auth", "payment", "user", "api"][i % 4]}`,
-      lastAlert: i % 15 === 0 ? `Disk usage at ${90 + (i % 10)}%` : null,
-    }));
-
-    const messages = [
-      { role: "user", content: "Check the fleet status", timestamp: Date.now() },
-      {
-        role: "assistant",
-        content: [
-          { type: "tool_use", id: "tu_fleet", name: "getFleetStatus", input: {} },
-        ],
-        timestamp: Date.now(),
-      },
-      {
-        role: "toolResult",
-        content: JSON.stringify(serverData),
-        tool_use_id: "tu_fleet",
-        timestamp: Date.now(),
-      },
-      { role: "user", content: "Which servers are critical?", timestamp: Date.now() },
-    ];
-
-    const result = await engine.assemble({
-      sessionId: "test-session",
-      messages,
-      model: "claude-sonnet-4-5",
-    });
-
-    console.log(
-      `  assemble(): estimatedTokens=${result.estimatedTokens}, ` +
-        `systemPrompt=${result.systemPromptAddition ? "yes" : "no"}`,
-    );
-
-    // Messages should be returned (compressed or not)
-    expect(result.messages.length).toBeGreaterThan(0);
-    // First and last messages should still be user messages
-    expect(result.messages[0].role).toBe("user");
-    expect(result.messages[result.messages.length - 1].role).toBe("user");
-    });
-
-    it("assemble() preserves small conversations", { timeout: 15000 }, async () => {
-    const messages = [
-      { role: "user", content: "Hello", timestamp: Date.now() },
-      { role: "assistant", content: "Hi there!", timestamp: Date.now() },
-    ];
-
-    const result = await engine.assemble({
-      sessionId: "test-session",
-      messages,
-    });
-
-    expect(result.messages).toHaveLength(2);
-    expect(result.messages[0].content).toBe("Hello");
-    expect(result.messages[1].content).toBe("Hi there!");
-    });
-
-    it("compact() returns success (compression handled in assemble)", async () => {
-    const result = await engine.compact({
-      sessionId: "test-session",
-      sessionFile: "/tmp/test.jsonl",
-    });
-
-    expect(result.ok).toBe(true);
-    expect(result.compacted).toBe(true);
-    });
-
-    it("getStats() returns compression statistics", () => {
-    const stats = engine.getStats();
-    expect(stats).toHaveProperty("totalCompressions");
-    expect(stats).toHaveProperty("totalTokensSaved");
-    expect(stats.totalCompressions).toBeGreaterThanOrEqual(0);
-    });
-  });
-}
diff --git a/tests/test_cli/test_wrap_openclaw.py b/tests/test_cli/test_wrap_openclaw.py
index 6b0444787..c600c57e8 100644
--- a/tests/test_cli/test_wrap_openclaw.py
+++ b/tests/test_cli/test_wrap_openclaw.py
@@ -67,6 +67,18 @@ def test_wrap_openclaw_default_installs_from_npm_and_restarts(runner: CliRunner)
     assert ["openclaw", "gateway", "restart"] in cmds
     assert ["openclaw", "plugins", "inspect", "headroom"] in cmds
 
+    config_set_index = next(
+        i
+        for i, cmd in enumerate(cmds)
+        if cmd[:4] == ["openclaw", "config", "set", "plugins.entries.headroom"]
+    )
+    install_index = next(
+        i
+        for i, cmd in enumerate(cmds)
+        if cmd[:4] == ["openclaw", "plugins", "install", "--dangerously-force-unsafe-install"]
+    )
+    assert config_set_index < install_index
+
     # Verify plugin install in npm mode does not set cwd
     install_call = next(
         c
@@ -91,6 +103,7 @@ def test_wrap_openclaw_default_installs_from_npm_and_restarts(runner: CliRunner)
     assert payload["config"]["autoStart"] is True
     assert payload["config"]["startupTimeoutMs"] == 20000
     assert payload["config"]["gatewayProviderIds"] == ["openai-codex"]
+    assert payload["config"]["pythonPath"] == wrap_cli.sys.executable
 
 
 def test_wrap_openclaw_skip_build_and_no_restart(runner: CliRunner, plugin_dir: Path) -> None:
@@ -330,6 +343,86 @@ def test_wrap_openclaw_accepts_repeatable_gateway_provider_ids(runner: CliRunner
     assert payload["config"]["gatewayProviderIds"] == ["openai-codex", "anthropic"]
 
 
+def test_normalize_openclaw_gateway_provider_ids_dedupes_blanks_and_defaults() -> None:
+    assert wrap_cli._normalize_openclaw_gateway_provider_ids(
+        (" openai-codex ", "", "anthropic", "openai-codex", "  ")
+    ) == ["openai-codex", "anthropic"]
+    assert wrap_cli._normalize_openclaw_gateway_provider_ids(None) == ["openai-codex"]
+
+
+def test_read_openclaw_config_value_handles_missing_and_raw_strings() -> None:
+    missing = MagicMock(returncode=1, stdout="", stderr="missing")
+    raw_string = MagicMock(returncode=0, stdout="plain-text-value\n", stderr="")
+
+    with patch("headroom.cli.wrap.subprocess.run", side_effect=[missing, raw_string]):
+        assert wrap_cli._read_openclaw_config_value("openclaw", "plugins.entries.headroom") is None
+        assert (
+            wrap_cli._read_openclaw_config_value(
+                "openclaw", "plugins.entries.headroom.config.pythonPath"
+            )
+            == "plain-text-value"
+        )
+
+
+def test_build_openclaw_plugin_entry_sets_and_clears_python_path() -> None:
+    with_python = wrap_cli._build_openclaw_plugin_entry(
+        existing_entry={"config": {"customFlag": True}},
+        proxy_port=8787,
+        startup_timeout_ms=20000,
+        python_path="C:\\Python312\\python.exe",
+        no_auto_start=False,
+        gateway_provider_ids=("openai-codex",),
+        enabled=True,
+    )
+    assert with_python["config"]["pythonPath"] == "C:\\Python312\\python.exe"
+
+    without_python = wrap_cli._build_openclaw_plugin_entry(
+        existing_entry={"config": {"pythonPath": "C:\\Old\\python.exe", "customFlag": True}},
+        proxy_port=8787,
+        startup_timeout_ms=20000,
+        python_path=None,
+        no_auto_start=False,
+        gateway_provider_ids=("openai-codex",),
+        enabled=True,
+    )
+    assert "pythonPath" not in without_python["config"]
+    assert without_python["config"]["customFlag"] is True
+
+
+def test_wrap_openclaw_no_auto_start_does_not_default_python_path(
+    runner: CliRunner, plugin_dir: Path
+) -> None:
+    calls: list[dict] = []
+
+    def which(name: str) -> str | None:
+        return {"openclaw": "openclaw", "npm": "npm"}.get(name)
+
+    with patch("headroom.cli.wrap.shutil.which", side_effect=which):
+        with patch("headroom.cli.wrap.subprocess.run", side_effect=_make_successful_run(calls)):
+            result = runner.invoke(
+                main,
+                [
+                    "wrap",
+                    "openclaw",
+                    "--plugin-path",
+                    str(plugin_dir),
+                    "--skip-build",
+                    "--no-auto-start",
+                    "--no-restart",
+                ],
+            )
+
+    assert result.exit_code == 0, result.output
+    set_entry = next(
+        c
+        for c in calls
+        if c["cmd"][:4] == ["openclaw", "config", "set", "plugins.entries.headroom"]
+    )
+    payload = json.loads(set_entry["cmd"][4])
+    assert payload["config"]["autoStart"] is False
+    assert "pythonPath" not in payload["config"]
+
+
 def test_wrap_openclaw_fails_for_npm_mode_hook_pack_bug_without_local_fallback(
     runner: CliRunner,
 ) -> None:
@@ -571,3 +664,37 @@ def test_unwrap_openclaw_no_restart_skips_gateway_restart(runner: CliRunner) ->
 
     assert result.exit_code == 0, result.output
     assert ["openclaw", "gateway", "restart"] not in [c["cmd"] for c in calls]
+
+
+def test_unwrap_openclaw_fails_when_openclaw_missing(runner: CliRunner) -> None:
+    with patch("headroom.cli.wrap.shutil.which", return_value=None):
+        result = runner.invoke(main, ["unwrap", "openclaw"])
+
+    assert result.exit_code != 0
+    assert "'openclaw' not found in PATH" in result.output
+
+
+def test_unwrap_openclaw_verbose_prints_gateway_and_inspect_output(runner: CliRunner) -> None:
+    def which(name: str) -> str | None:
+        return {"openclaw": "openclaw"}.get(name)
+
+    def run(cmd, **kwargs):  # noqa: ANN001
+        if cmd[:4] == ["openclaw", "config", "get", "plugins.entries.headroom"]:
+            return MagicMock(
+                returncode=0,
+                stdout=json.dumps({"enabled": True, "config": {"proxyPort": 8787}}),
+                stderr="",
+            )
+        if cmd[:3] == ["openclaw", "gateway", "restart"]:
+            return MagicMock(returncode=0, stdout="gateway-restarted", stderr="")
+        if cmd[:3] == ["openclaw", "plugins", "inspect"]:
+            return MagicMock(returncode=0, stdout="inspect-disabled", stderr="")
+        return MagicMock(returncode=0, stdout="", stderr="")
+
+    with patch("headroom.cli.wrap.shutil.which", side_effect=which):
+        with patch("headroom.cli.wrap.subprocess.run", side_effect=run):
+            result = runner.invoke(main, ["unwrap", "openclaw", "--verbose"])
+
+    assert result.exit_code == 0, result.output
+    assert "gateway-restarted" in result.output
+    assert "inspect-disabled" in result.output
diff --git a/tests/test_openai_codex_routing.py b/tests/test_openai_codex_routing.py
index bbdcb3e71..95f2d16ec 100644
--- a/tests/test_openai_codex_routing.py
+++ b/tests/test_openai_codex_routing.py
@@ -1,7 +1,17 @@
 import base64
 import json
+import sys
+from types import SimpleNamespace
+from unittest.mock import MagicMock, patch
 
-from headroom.proxy.handlers.openai import _resolve_codex_routing_headers
+import anyio
+import pytest
+from fastapi import Request
+
+from headroom.proxy.handlers.openai import (
+    OpenAIHandlerMixin,
+    _resolve_codex_routing_headers,
+)
 
 
 def _jwt(payload: dict) -> str:
@@ -56,3 +66,152 @@ def test_resolve_codex_routing_leaves_regular_openai_bearer_tokens_unchanged():
 
     assert is_chatgpt is False
     assert "ChatGPT-Account-ID" not in headers
+
+
+def test_resolve_codex_routing_returns_none_without_bearer_auth():
+    headers, is_chatgpt = _resolve_codex_routing_headers({})
+
+    assert is_chatgpt is False
+    assert headers == {}
+
+
+def test_resolve_codex_routing_ignores_non_jwt_bearer_tokens():
+    headers, is_chatgpt = _resolve_codex_routing_headers(
+        {
+            "authorization": "Bearer not-a-jwt",
+        }
+    )
+
+    assert is_chatgpt is False
+    assert headers["authorization"] == "Bearer not-a-jwt"
+
+
+def test_resolve_codex_routing_ignores_invalid_jwt_payloads():
+    invalid_payload = base64.urlsafe_b64encode(b"not-json").decode("ascii").rstrip("=")
+    token = f"test-header.{invalid_payload}.signature"
+
+    headers, is_chatgpt = _resolve_codex_routing_headers(
+        {
+            "authorization": f"Bearer {token}",
+        }
+    )
+
+    assert is_chatgpt is False
+    assert headers["authorization"] == f"Bearer {token}"
+
+
+class _DummyMetrics:
+    async def record_request(self, **kwargs):  # noqa: ANN003
+        return None
+
+    async def record_failed(self):
+        return None
+
+
+class _DummyTokenizer:
+    def count_messages(self, messages):
+        return len(messages)
+
+
+class _ResponseStub:
+    def json(self):
+        return {"usage": {"input_tokens": 2, "output_tokens": 1}}
+
+
+class _DummyOpenAIHandler(OpenAIHandlerMixin):
+    OPENAI_API_URL = "https://api.openai.com"
+
+    def __init__(self) -> None:
+        self.rate_limiter = None
+        self.metrics = _DummyMetrics()
+        self.config = SimpleNamespace(optimize=False)
+        self.usage_reporter = None
+        self.openai_provider = SimpleNamespace()
+        self.anthropic_backend = None
+        self.cost_tracker = None
+        self.captured_request: tuple[str, str, dict, dict] | None = None
+
+    async def _next_request_id(self) -> str:
+        return "req-1"
+
+    def _extract_tags(self, headers: dict[str, str]) -> list[str]:
+        return []
+
+    async def _retry_request(self, method: str, url: str, headers: dict, body: dict):
+        self.captured_request = (method, url, headers, body)
+        return _ResponseStub()
+
+
+def _build_request(body: dict, headers: dict[str, str]) -> Request:
+    payload = json.dumps(body).encode("utf-8")
+
+    async def receive():
+        return {"type": "http.request", "body": payload, "more_body": False}
+
+    scope = {
+        "type": "http",
+        "asgi": {"version": "3.0"},
+        "http_version": "1.1",
+        "method": "POST",
+        "scheme": "https",
+        "path": "/v1/responses",
+        "raw_path": b"/v1/responses",
+        "query_string": b"",
+        "headers": [
+            (key.lower().encode("utf-8"), value.encode("utf-8")) for key, value in headers.items()
+        ],
+        "client": ("127.0.0.1", 12345),
+        "server": ("testserver", 443),
+    }
+    return Request(scope, receive)
+
+
+def test_handle_openai_responses_routes_chatgpt_auth_to_backend_api(monkeypatch):
+    token = _jwt(
+        {
+            "https://api.openai.com/auth": {
+                "chatgpt_account_id": "acct-from-jwt",
+            }
+        }
+    )
+    request = _build_request(
+        {"model": "gpt-5.4", "input": "hello"},
+        {"Authorization": f"Bearer {token}"},
+    )
+    handler = _DummyOpenAIHandler()
+
+    monkeypatch.setattr("headroom.tokenizers.get_tokenizer", lambda model: _DummyTokenizer())
+
+    anyio.run(handler.handle_openai_responses, request)
+
+    assert handler.captured_request is not None
+    method, url, headers, body = handler.captured_request
+    assert method == "POST"
+    assert url == "https://chatgpt.com/backend-api/codex/responses"
+    assert headers["ChatGPT-Account-ID"] == "acct-from-jwt"
+    assert body["input"] == "hello"
+
+
+class _DummyWebSocket:
+    def __init__(self, headers: dict[str, str]):
+        self.headers = headers
+        self.accepted_subprotocol = None
+
+    async def accept(self, subprotocol=None):
+        self.accepted_subprotocol = subprotocol
+
+
+def test_handle_openai_responses_ws_resolves_codex_routing_headers():
+    class SentinelError(RuntimeError):
+        pass
+
+    handler = _DummyOpenAIHandler()
+    websocket = _DummyWebSocket({"authorization": "Bearer token"})
+
+    with patch.dict(sys.modules, {"websockets": MagicMock()}):
+        with patch(
+            "headroom.proxy.handlers.openai._resolve_codex_routing_headers",
+            side_effect=SentinelError("resolved"),
+        ):
+            with pytest.raises(SentinelError, match="resolved"):
+                anyio.run(handler.handle_openai_responses_ws, websocket)