diff --git a/src/agent_env/agents/README.md b/src/agent_env/agents/README.md
index 43872d88c..1be4e6582 100644
--- a/src/agent_env/agents/README.md
+++ b/src/agent_env/agents/README.md
@@ -24,7 +24,8 @@ run it. The CLI's version is the Dockerfile's
 `node`, without npm or npx, and the Python packages `model-requirements.txt` pins. A `deploy_agent` `builtin_tools`
 selection picks the CLI's own tools: `{"disable": "*"}` and `{"only": [...]}` become its `--tools` list, a list to
 turn off becomes `--disallowedTools`, which keeps the CLI's defaults for the rest, and any selection adds
-`--strict-mcp-config`, so its MCP servers are only the task env's. The names are `ClaudeCodeTool`'s in
+`--strict-mcp-config`, so its MCP servers are only the task env's. Tool search is off unless the agent's environment sets
+`ENABLE_TOOL_SEARCH`, so the CLI sends the env's tools and its own up front. The names are `ClaudeCodeTool`'s in
 `claude_bridge.py`: every tool the pinned CLI has, though which it offers by default depends on the model. A test fails
 when the Dockerfile's `CLAUDE_CODE_VERSION` moves, until `ClaudeCodeTool` and `TOOLS_CLI_VERSION` move with it.
 
diff --git a/src/agent_env/agents/agents/claude-code/Dockerfile b/src/agent_env/agents/agents/claude-code/Dockerfile
index 99d8539ae..cbe95d6e6 100644
--- a/src/agent_env/agents/agents/claude-code/Dockerfile
+++ b/src/agent_env/agents/agents/claude-code/Dockerfile
@@ -6,7 +6,7 @@ FROM public.ecr.aws/docker/library/python:3.11-slim@sha256:c20888b6acdd1e63e1c43
 RUN apt-get update && apt-get install -y --no-install-recommends ca-certificates curl poppler-utils \
     && rm -rf /var/lib/apt/lists/*
 # Claude Code's native build for this machine's platform, checked against its release manifest.
-ARG CLAUDE_CODE_VERSION=2.1.280
+ARG CLAUDE_CODE_VERSION=2.1.322
 RUN set -eu; \
     case "$(uname -m)" in x86_64) platform=linux-x64 ;; aarch64) platform=linux-arm64 ;; \
       *) echo "Claude Code has no build for $(uname -m)" >&2; exit 1 ;; esac; \
diff --git a/src/agent_env/agents/agents/claude-code/claude_bridge.py b/src/agent_env/agents/agents/claude-code/claude_bridge.py
index cecd8286f..fad10df25 100644
--- a/src/agent_env/agents/agents/claude-code/claude_bridge.py
+++ b/src/agent_env/agents/agents/claude-code/claude_bridge.py
@@ -56,11 +56,11 @@ def project_dir(workspace: Path) -> Path:
 
 
 # The CLI version ClaudeCodeTool names the tools of; a test holds it to the Dockerfile's CLAUDE_CODE_VERSION.
-TOOLS_CLI_VERSION = "2.1.280"
+TOOLS_CLI_VERSION = "2.1.322"
 # The CLI's own tools, by the names its model sees. Which of them it offers by default depends on the model, and its MCP
 # resource tools come only with MCP servers.
 ClaudeCodeTool = Literal["Agent", "Bash", "CronCreate", "CronDelete", "CronList", "Edit", "EnterWorktree",
-                         "ExitWorktree", "ListAgents", "ListMcpResourcesTool", "NotebookEdit", "Read",
+                         "ExitWorktree", "ListAgents", "ListMcpResourcesTool", "Monitor", "NotebookEdit", "Read",
                          "ReadMcpResourceDirTool", "ReadMcpResourceTool", "ReportFindings", "ScheduleWakeup",
                          "SendMessage", "Skill", "TaskCreate", "TaskGet", "TaskList", "TaskStop", "TaskUpdate",
                          "WebFetch", "WebSearch", "Workflow", "Write"]
@@ -194,6 +194,8 @@ def cli_env(environ: Mapping[str, str], *, model: str | None = None, project_id:
         env["ANTHROPIC_CUSTOM_HEADERS"] = "\n".join(f"{name}: {value}" for name, value in headers.items())
     if max_thinking_tokens:
         env["MAX_THINKING_TOKENS"] = str(max_thinking_tokens)
+    # Left on, the CLI sends no MCP tool and only some of its own until the model searches for them.
+    env.setdefault("ENABLE_TOOL_SEARCH", "false")
     # Older CLIs prepend a changing attribution block to the system prompt on custom base URLs, which defeats the
     # provider's prefix cache.
     env["CLAUDE_CODE_ATTRIBUTION_HEADER"] = "0"
@@ -593,8 +595,8 @@ async def feed_stdin() -> None:
 
 # Behind a gateway the CLI gives a bare id of these a 200K window, and envs whose tool definitions alone pass that
 # make it exit with "Autocompact is thrashing". Add a model only once the pinned CLI maps its [1m] form.
-_NATIVE_1M_MODELS = frozenset({"claude-opus-5", "claude-opus-5-5", "claude-fable-5-1", "claude-opus-4-8",
-                               "claude-opus-4-7"})
+_NATIVE_1M_MODELS = frozenset({"claude-opus-5", "claude-opus-5-5", "claude-fable-5-1", "claude-fable-5-2",
+                               "claude-opus-4-8", "claude-opus-4-7"})
 
 
 def _with_1m_window(model: str) -> str:
diff --git a/tst/integration/cli/run_bundle_claude_code_install_test.py b/tst/integration/cli/run_bundle_claude_code_install_test.py
index f3b76d0af..47b4fc068 100644
--- a/tst/integration/cli/run_bundle_claude_code_install_test.py
+++ b/tst/integration/cli/run_bundle_claude_code_install_test.py
@@ -135,7 +135,8 @@ def test_a_retried_install_replaces_the_agent_an_earlier_attempt_left_running_in
     """The first turn fails, and its retry installs again into the same container, on the same port, while the
     first install's agent still runs there."""
     endpoint.respond = tool_then_answer("Bash", {"command": f"cat notes.txt; pwd; {READ_SKILL}"})
-    endpoint.fail_next(Fault("status", status=400))
+    # A 403, which the CLI never resends; a 400 it resends without some of its betas.
+    endpoint.fail_next(Fault("status", status=403))
     bundle = _bundle(state / "bundle", "debian")
     task = bundle / "tasks/install.json"
     steps = json.loads(task.read_text())
@@ -190,7 +191,8 @@ def test_a_retried_host_install_stops_the_agent_an_earlier_attempt_started(monke
     """install_agent empties its work dir before each attempt, so the first install's agent must live outside it:
     found there, it is stopped, rather than keeping the port the retry's agent needs."""
     endpoint.respond = tool_then_answer("Bash", {"command": f"echo {NOTES}; {READ_SKILL}"})
-    endpoint.fail_next(Fault("status", status=400))
+    # A 403, which the CLI never resends; a 400 it resends without some of its betas.
+    endpoint.fail_next(Fault("status", status=403))
     bundle = _bundle(state / "bundle", None, agents=("helper",))
     task = bundle / "tasks/install.json"
     steps = json.loads(task.read_text())
diff --git a/tst/unit/agents/claude_code/test_claude_bridge_model.py b/tst/unit/agents/claude_code/test_claude_bridge_model.py
index 702f2208f..c8f876a3b 100644
--- a/tst/unit/agents/claude_code/test_claude_bridge_model.py
+++ b/tst/unit/agents/claude_code/test_claude_bridge_model.py
@@ -11,8 +11,8 @@ def _cli_model(model: str | None) -> str | None:
     return cmd[cmd.index("--model") + 1] if "--model" in cmd else None
 
 
-@pytest.mark.parametrize("model", ["claude-opus-5-5", "claude-opus-5", "claude-fable-5-1", "claude-opus-4-8",
-                                   "claude-opus-4-7"])
+@pytest.mark.parametrize("model", ["claude-opus-5-5", "claude-opus-5", "claude-fable-5-1", "claude-fable-5-2",
+                                   "claude-opus-4-8", "claude-opus-4-7"])
 def test_a_native_1m_model_gets_its_1m_window(model):
     assert _cli_model(model) == f"{model}[1m]"
 
diff --git a/tst/unit/agents/claude_code/test_cli_env.py b/tst/unit/agents/claude_code/test_cli_env.py
index 443f4940a..7c92fcc82 100644
--- a/tst/unit/agents/claude_code/test_cli_env.py
+++ b/tst/unit/agents/claude_code/test_cli_env.py
@@ -41,6 +41,11 @@ def test_anthropic_variables_already_set_are_kept():
     assert (env["ANTHROPIC_AUTH_TOKEN"], env["ANTHROPIC_BASE_URL"]) == ("own", "https://own.example")
 
 
+def test_the_cli_offers_its_tools_up_front_unless_tool_search_is_asked_for():
+    assert claude_bridge.cli_env(GATEWAY)["ENABLE_TOOL_SEARCH"] == "false"
+    assert claude_bridge.cli_env({**GATEWAY, "ENABLE_TOOL_SEARCH": "auto"})["ENABLE_TOOL_SEARCH"] == "auto"
+
+
 def test_no_endpoint_leaves_the_cli_to_its_own_and_an_api_key_alone():
     env = claude_bridge.cli_env({"ANTHROPIC_API_KEY": "direct"}, model="claude-x")
 
@@ -141,7 +146,7 @@ async def _exec(*cmd, **kwargs):
 
 @pytest.mark.parametrize("workspace, project", [
     ("/app", "-app"),
-    ("/workspaces/my_ws.x-y/Sub Dir", "-workspaces-my-ws-x-y-Sub-Dir"),  # as the CLI names it, checked against 2.1.280
+    ("/workspaces/my_ws.x-y/Sub Dir", "-workspaces-my-ws-x-y-Sub-Dir"),  # as the CLI names it, checked against 2.1.322
 ])
 def test_a_sessions_transcripts_are_where_the_cli_keeps_them_for_its_workspace(workspace, project):
     assert claude_bridge.project_dir(Path(workspace)) == claude_bridge.CLAUDE_STATE_DIR / "projects" / project