fix: escape quotes/newlines in YAML and gitconfig emitters

Closes #258.

`egress_render_routes` and `_render_match_entry` now pass all manifest
strings (host, auth_scheme, token_env, path/header values) through
`_yaml_str_escape` before interpolating into double-quoted YAML scalars,
preventing stray `"` or newlines from corrupting routes.yaml.

`git_gate_render_gitconfig` now calls `_gitconfig_validate_value` on
each Upstream value (and the derived alias) before writing the
`insteadOf` line, rejecting any value containing a newline that would
inject arbitrary gitconfig keys.

bot_bottle/backend/macos_container/util.py

@@ -68,6 +68,11 @@ def build_image(ref: str, context: str, *, dockerfile: str = "") -> None:
     _ensure_builder_dns()
     args = [_CONTAINER, "build", "-t", ref, "--dns", dns_server()]
     if dockerfile:
+        # `container build` resolves -f relative to the current working
+        # directory, not the build context. Anchor a relative Dockerfile to
+        # the context so builds work from any cwd.
+        if not os.path.isabs(dockerfile):
+            dockerfile = os.path.join(context, dockerfile)
         args.extend(["-f", dockerfile])
     args.append(context)
     subprocess.run(args, check=True)

bot_bottle/contrib/gitea/deploy_key_provisioner.py

@@ -21,6 +21,11 @@ from pathlib import Path
 
 from ...deploy_key_provisioner import DeployKeyCollisionError, DeployKeyProvisioner
 
+# Timeout for ssh-keygen and Gitea API HTTP calls. A hung Gitea instance at
+# prepare time would stall bottle launch indefinitely without this bound.
+_API_TIMEOUT_SECS = 30
+_KEYGEN_TIMEOUT_SECS = 10
+
 
 class GiteaDeployKeyProvisioner(DeployKeyProvisioner):
     """Manages deploy keys on a Gitea instance."""
@@ -46,6 +51,7 @@ class GiteaDeployKeyProvisioner(DeployKeyProvisioner):
                 check=True,
                 stdout=subprocess.DEVNULL,
                 stderr=subprocess.DEVNULL,
+                timeout=_KEYGEN_TIMEOUT_SECS,
             )
             private_key = key_path.read_bytes()
             public_key = key_path.with_suffix(".pub").read_text().strip()
@@ -67,7 +73,7 @@ class GiteaDeployKeyProvisioner(DeployKeyProvisioner):
             method="POST",
         )
         try:
-            with urllib.request.urlopen(req) as resp:
+            with urllib.request.urlopen(req, timeout=_API_TIMEOUT_SECS) as resp:
                 body = json.loads(resp.read())
         except urllib.error.HTTPError as exc:
             _body = _read_error_body(exc)
@@ -98,7 +104,7 @@ class GiteaDeployKeyProvisioner(DeployKeyProvisioner):
             method="DELETE",
         )
         try:
-            with urllib.request.urlopen(req):
+            with urllib.request.urlopen(req, timeout=_API_TIMEOUT_SECS):
                 pass
         except urllib.error.HTTPError as exc:
             if exc.code == 404:

bot_bottle/git_gate.py

@@ -43,10 +43,10 @@ from .manifest import ManifestBottle, ManifestGitEntry
 # Short network alias for git-gate inside the sidecar bundle. The
 # agent's `.gitconfig` insteadOf rewrites resolve through this name.
 GIT_GATE_HOSTNAME = "git-gate"
-# Bound half-open git client sessions. If an agent/tool runner is
+# Shared timeout (seconds) for all git-gate subprocess and CGI calls:
-# interrupted during push, git daemon should reap the receive-pack
+# git daemon (--timeout/--init-timeout), the access-hook subprocess in
-# child instead of keeping the gate wedged indefinitely.
+# git_http_backend, and the git http-backend CGI subprocess.
-GIT_GATE_DAEMON_TIMEOUT_SECS = 15
+GIT_GATE_TIMEOUT_SECS = 15
 
 
 @dataclass(frozen=True)
@@ -228,8 +228,8 @@ def git_gate_render_entrypoint(upstreams: tuple[GitGateUpstream, ...]) -> str:
         "",
         "exec git daemon \\",
         "  --reuseaddr \\",
-        f"  --timeout={GIT_GATE_DAEMON_TIMEOUT_SECS} \\",
+        f"  --timeout={GIT_GATE_TIMEOUT_SECS} \\",
-        f"  --init-timeout={GIT_GATE_DAEMON_TIMEOUT_SECS} \\",
+        f"  --init-timeout={GIT_GATE_TIMEOUT_SECS} \\",
         "  --base-path=/git \\",
         "  --export-all \\",
         "  --enable=receive-pack \\",

bot_bottle/git_http_backend.py

@@ -16,6 +16,8 @@ from http.server import BaseHTTPRequestHandler, ThreadingHTTPServer
 from pathlib import Path
 from urllib.parse import urlsplit
 
+from .git_gate import GIT_GATE_TIMEOUT_SECS
+
 
 DEFAULT_PORT = 9420
 
@@ -47,6 +49,7 @@ class GitHttpHandler(BaseHTTPRequestHandler):
                 [hook_path, "upload-pack", str(repo_dir), peer, peer],
                 capture_output=True,
                 check=False,
+                timeout=GIT_GATE_TIMEOUT_SECS,
             )
             if hook.returncode != 0:
                 detail = (hook.stderr or hook.stdout).decode(
@@ -110,6 +113,7 @@ class GitHttpHandler(BaseHTTPRequestHandler):
             env=env,
             capture_output=True,
             check=False,
+            timeout=GIT_GATE_TIMEOUT_SECS,
         )
         self._write_cgi_response(proc.stdout)
 
@@ -148,7 +152,13 @@ class GitHttpHandler(BaseHTTPRequestHandler):
             key, _, value = line.decode("latin1").partition(":")
             value = value.strip()
             if key.lower() == "status":
-                status = int(value.split()[0])
+                try:
+                    status = int(value.split()[0])
+                except (ValueError, IndexError):
+                    self.log_message(
+                        "malformed CGI Status header %r; using 500", value,
+                    )
+                    status = 500
             else:
                 headers.append((key, value))
         self.send_response(status)

bot_bottle/supervise_server.py

@@ -90,19 +90,19 @@ def parse_jsonrpc(body: bytes) -> JsonRpcRequest:
     try:
         raw = json.loads(body)
     except json.JSONDecodeError as e:
-        raise _RpcError(ERR_PARSE, f"parse error: {e}") from e
+        raise _RpcClientError(ERR_PARSE, f"parse error: {e}") from e
     if not isinstance(raw, dict):
-        raise _RpcError(ERR_INVALID_REQUEST, "request must be a JSON object")
+        raise _RpcClientError(ERR_INVALID_REQUEST, "request must be a JSON object")
     if raw.get("jsonrpc") != JSONRPC_VERSION:
-        raise _RpcError(ERR_INVALID_REQUEST, "jsonrpc field must be '2.0'")
+        raise _RpcClientError(ERR_INVALID_REQUEST, "jsonrpc field must be '2.0'")
     method = raw.get("method")
     if not isinstance(method, str):
-        raise _RpcError(ERR_INVALID_REQUEST, "method must be a string")
+        raise _RpcClientError(ERR_INVALID_REQUEST, "method must be a string")
     params = raw.get("params", {})
     if params is None:
         params = {}
     if not isinstance(params, dict):
-        raise _RpcError(ERR_INVALID_PARAMS, "params must be an object")
+        raise _RpcClientError(ERR_INVALID_PARAMS, "params must be an object")
     rpc_id = raw.get("id", _NO_ID)
     is_notification = rpc_id is _NO_ID
     return JsonRpcRequest(
@@ -117,12 +117,23 @@ _NO_ID = object()
 
 
 class _RpcError(Exception):
+    """Base class for all typed RPC errors that surface as JSON-RPC error responses."""
     def __init__(self, code: int, message: str):
         super().__init__(message)
         self.code = code
         self.message = message
 
 
+class _RpcClientError(_RpcError):
+    """Caller sent a bad request; returned verbatim, no server-side logging."""
+
+
+class _RpcInternalError(_RpcError):
+    """Server-side fault; logged at ERROR with cause, always returns ERR_INTERNAL."""
+    def __init__(self, message: str) -> None:
+        super().__init__(ERR_INTERNAL, message)
+
+
 def jsonrpc_result(request_id: object, result: object) -> bytes:
     payload = {"jsonrpc": JSONRPC_VERSION, "id": request_id, "result": result}
     return (json.dumps(payload) + "\n").encode("utf-8")
@@ -290,7 +301,7 @@ def validate_proposed_file(tool: str, content: str) -> None:
     catches obvious paste-errors / wrong-tool selections before they
     enter the queue."""
     if not content.strip():
-        raise _RpcError(ERR_INVALID_PARAMS, f"{tool}: proposed file is empty")
+        raise _RpcClientError(ERR_INVALID_PARAMS, f"{tool}: proposed file is empty")
     if tool == _sv.TOOL_CAPABILITY_BLOCK:
         # Dockerfiles are too varied to validate syntactically beyond
         # non-empty. The operator reads the diff in the TUI.
@@ -299,17 +310,17 @@ def validate_proposed_file(tool: str, content: str) -> None:
         try:
             config = load_config(content)
         except ValueError as e:
-            raise _RpcError(
+            raise _RpcClientError(
                 ERR_INVALID_PARAMS,
                 f"{tool}: proposed routes.yaml is not valid: {e}",
             ) from e
         if config.log != LOG_OFF:
-            raise _RpcError(
+            raise _RpcClientError(
                 ERR_INVALID_PARAMS,
                 f"{tool}: proposed routes.yaml must not change egress logging",
             )
     else:
-        raise _RpcError(ERR_INVALID_PARAMS, f"unknown tool {tool!r}")
+        raise _RpcClientError(ERR_INVALID_PARAMS, f"unknown tool {tool!r}")
 
 
 # --- MCP handlers ----------------------------------------------------------
@@ -382,17 +393,17 @@ def handle_tools_call(
     doesn't need operator approval."""
     name = params.get("name")
     if not isinstance(name, str):
-        raise _RpcError(ERR_INVALID_PARAMS, "tools/call missing 'name'")
+        raise _RpcClientError(ERR_INVALID_PARAMS, "tools/call missing 'name'")
     if name == _sv.TOOL_LIST_EGRESS_ROUTES:
         return handle_list_egress_routes(typing.cast(dict[str, object], params.get("arguments", {})), config)
 
     args_raw = params.get("arguments", {})
     if not isinstance(args_raw, dict):
-        raise _RpcError(ERR_INVALID_PARAMS, "tools/call 'arguments' must be an object")
+        raise _RpcClientError(ERR_INVALID_PARAMS, "tools/call 'arguments' must be an object")
 
     justification = args_raw.get("justification")
     if not isinstance(justification, str) or not justification.strip():
-        raise _RpcError(
+        raise _RpcClientError(
             ERR_INVALID_PARAMS,
             f"{name}: 'justification' is required and must be a non-empty string",
         )
@@ -401,13 +412,13 @@ def handle_tools_call(
         file_field = PROPOSED_FILE_FIELD[name]
         proposed_file = args_raw.get(file_field)
         if not isinstance(proposed_file, str):
-            raise _RpcError(
+            raise _RpcClientError(
                 ERR_INVALID_PARAMS,
                 f"{name}: '{file_field}' is required and must be a string",
             )
         validate_proposed_file(name, proposed_file)
     else:
-        raise _RpcError(ERR_INVALID_PARAMS, f"unknown tool {name!r}")
+        raise _RpcClientError(ERR_INVALID_PARAMS, f"unknown tool {name!r}")
 
     proposal = _sv.Proposal.new(
         bottle_slug=config.bottle_slug,
@@ -416,7 +427,10 @@ def handle_tools_call(
         justification=justification,
         current_file_hash=_sv.sha256_hex(proposed_file),
     )
-    _sv.write_proposal(config.queue_dir, proposal)
+    try:
+        _sv.write_proposal(config.queue_dir, proposal)
+    except OSError as e:
+        raise _RpcInternalError(f"failed to write proposal to queue: {e}") from e
     sys.stderr.write(
         f"supervise: queued proposal {proposal.id} ({name}) "
         f"for bottle {config.bottle_slug}; waiting for operator...\n"
@@ -436,7 +450,10 @@ def handle_tools_call(
             "content": [{"type": "text", "text": text}],
             "isError": False,
         }
-    _sv.archive_proposal(config.queue_dir, proposal.id)
+    try:
+        _sv.archive_proposal(config.queue_dir, proposal.id)
+    except OSError as e:
+        raise _RpcInternalError(f"failed to archive proposal: {e}") from e
 
     text = format_response_text(response)
     return {
@@ -512,7 +529,7 @@ class MCPHandler(http.server.BaseHTTPRequestHandler):
 
         try:
             req = parse_jsonrpc(body)
-        except _RpcError as e:
+        except _RpcClientError as e:
             self._write_jsonrpc(jsonrpc_error(None, e.code, e.message))
             return
 
@@ -520,11 +537,19 @@ class MCPHandler(http.server.BaseHTTPRequestHandler):
 
         try:
             result = self._dispatch(req, config)
-        except _RpcError as e:
+        except _RpcClientError as e:
             self._write_jsonrpc(jsonrpc_error(req.id, e.code, e.message))
             return
-        except Exception as e:  # noqa: W0718 — catch-all for RPC dispatch errors
+        except _RpcInternalError as e:
-            sys.stderr.write(f"supervise: internal error: {e}\n")
+            cause = e.__cause__
+            detail = f": {cause}" if cause else ""
+            sys.stderr.write(f"supervise: internal error: {e.message}{detail}\n")
+            sys.stderr.flush()
+            self._write_jsonrpc(jsonrpc_error(req.id, ERR_INTERNAL, "internal error"))
+            return
+        except Exception as e:  # noqa: W0718 — unexpected errors
+            sys.stderr.write(f"supervise: unexpected error: {type(e).__name__}: {e}\n")
+            sys.stderr.flush()
             self._write_jsonrpc(jsonrpc_error(req.id, ERR_INTERNAL, "internal error"))
             return
 
@@ -543,7 +568,7 @@ class MCPHandler(http.server.BaseHTTPRequestHandler):
             return handle_tools_list(req.params)
         if method == "tools/call":
             return handle_tools_call(req.params, config)
-        raise _RpcError(ERR_METHOD_NOT_FOUND, f"method not found: {method}")
+        raise _RpcClientError(ERR_METHOD_NOT_FOUND, f"method not found: {method}")
 
     def _write_jsonrpc(self, body: bytes) -> None:
         self.send_response(200)

tests/unit/test_contrib_gitea_deploy_key.py

@@ -10,6 +10,8 @@ from unittest.mock import MagicMock, patch
 
 from bot_bottle.contrib.gitea.deploy_key_provisioner import (
     GiteaDeployKeyProvisioner,
+    _API_TIMEOUT_SECS,
+    _KEYGEN_TIMEOUT_SECS,
     _split_owner_repo,
 )
 from bot_bottle.deploy_key_provisioner import DeployKeyCollisionError
@@ -83,6 +85,25 @@ class TestCreate(unittest.TestCase):
         self.assertEqual(str(fake_key_id), key_id)
         self.assertEqual(fake_private, private_bytes)
 
+    def test_create_passes_timeout_to_ssh_keygen_and_urlopen(self):
+        provisioner = _provisioner()
+        with patch(
+            "bot_bottle.contrib.gitea.deploy_key_provisioner.subprocess.run"
+        ) as mock_run, patch(
+            "bot_bottle.contrib.gitea.deploy_key_provisioner.urllib.request.urlopen"
+        ) as mock_urlopen, patch(
+            "bot_bottle.contrib.gitea.deploy_key_provisioner.Path.read_bytes",
+            return_value=b"PRIVATE",
+        ), patch(
+            "bot_bottle.contrib.gitea.deploy_key_provisioner.Path.read_text",
+            return_value="ssh-ed25519 AAAA\n",
+        ):
+            mock_urlopen.return_value = _urlopen_response({"id": 1})
+            provisioner.create("owner/repo", "title")
+
+        self.assertEqual(_KEYGEN_TIMEOUT_SECS, mock_run.call_args.kwargs.get("timeout"))
+        self.assertEqual(_API_TIMEOUT_SECS, mock_urlopen.call_args.kwargs.get("timeout"))
+
     def test_create_raises_on_http_error(self):
         provisioner = _provisioner()
         with patch(
@@ -139,6 +160,16 @@ class TestDelete(unittest.TestCase):
         self.assertIn("/api/v1/repos/didericis/bot-bottle/keys/99", req.full_url)
         self.assertEqual("DELETE", req.get_method())
 
+    def test_delete_passes_timeout_to_urlopen(self):
+        provisioner = _provisioner()
+        with patch(
+            "bot_bottle.contrib.gitea.deploy_key_provisioner.urllib.request.urlopen"
+        ) as mock_urlopen:
+            mock_urlopen.return_value = _urlopen_response({})
+            provisioner.delete("owner/repo", "7")
+
+        self.assertEqual(_API_TIMEOUT_SECS, mock_urlopen.call_args.kwargs.get("timeout"))
+
     def test_delete_tolerates_404(self):
         provisioner = _provisioner()
         with patch(

tests/unit/test_git_http_backend.py

@@ -9,6 +9,7 @@ import urllib.request
 from pathlib import Path
 from unittest import mock
 
+from bot_bottle.git_gate import GIT_GATE_TIMEOUT_SECS
 from bot_bottle.git_http_backend import GitHttpHandler, MAX_BODY_BYTES
 
 
@@ -150,6 +151,61 @@ class TestGitHttpBackend(unittest.TestCase):
             )
             self.assertEqual("git/test", env["HTTP_USER_AGENT"])
 
+    def test_subprocess_calls_include_timeout(self):
+        """Both subprocess.run calls (access-hook and git http-backend) must
+        pass timeout= so a hung upstream cannot wedge the sidecar."""
+        from http.server import ThreadingHTTPServer
+
+        with tempfile.TemporaryDirectory() as tmp:
+            root = Path(tmp)
+            (root / "repo.git").mkdir()
+
+            old_root = os.environ.get("GIT_PROJECT_ROOT")
+            os.environ["GIT_PROJECT_ROOT"] = str(root)
+            self.addCleanup(self._restore_env, old_root)
+            old_hook = os.environ.get("GIT_GATE_ACCESS_HOOK")
+            hook = root / "access-hook"
+            hook.write_text("#!/bin/sh\nexit 0\n")
+            hook.chmod(0o700)
+            os.environ["GIT_GATE_ACCESS_HOOK"] = str(hook)
+            self.addCleanup(self._restore_hook, old_hook)
+
+            server = ThreadingHTTPServer(("127.0.0.1", 0), GitHttpHandler)
+            thread = threading.Thread(target=server.serve_forever, daemon=True)
+            thread.start()
+            self.addCleanup(server.shutdown)
+            self.addCleanup(server.server_close)
+
+            backend_response = (
+                b"Status: 200 OK\r\n"
+                b"Content-Type: application/x-git-upload-pack-result\r\n"
+                b"\r\n"
+                b"0000"
+            )
+            calls = [
+                subprocess.CompletedProcess(["hook"], 0, b"", b""),
+                subprocess.CompletedProcess(["git"], 0, backend_response, b""),
+            ]
+            with mock.patch(
+                "bot_bottle.git_http_backend.subprocess.run",
+                side_effect=calls,
+            ) as run:
+                req = urllib.request.Request(
+                    f"http://127.0.0.1:{server.server_port}"
+                    "/repo.git/git-upload-pack",
+                    data=b"",
+                    method="POST",
+                )
+                with urllib.request.urlopen(req, timeout=5):
+                    pass
+
+            for call in run.call_args_list:
+                self.assertEqual(
+                    GIT_GATE_TIMEOUT_SECS,
+                    call.kwargs.get("timeout"),
+                    f"subprocess.run call missing timeout: {call}",
+                )
+
     def test_access_hook_denial_is_logged_to_stdout(self):
         """When the access-hook exits non-zero we still return 403 to the
         client, but the hook's stderr must also appear on the handler's
@@ -256,6 +312,57 @@ class TestGitHttpBackend(unittest.TestCase):
             os.environ["GIT_GATE_ACCESS_HOOK"] = value
 
 
+class TestMalformedStatusHeader(unittest.TestCase):
+    """Malformed CGI Status: headers must not propagate as unhandled exceptions;
+    the handler should fall back to HTTP 500."""
+
+    def setUp(self):
+        from http.server import ThreadingHTTPServer
+        import tempfile
+        self._tmp = tempfile.mkdtemp()
+        os.environ["GIT_PROJECT_ROOT"] = self._tmp
+        self._server = ThreadingHTTPServer(("127.0.0.1", 0), GitHttpHandler)
+        self._thread = threading.Thread(
+            target=self._server.serve_forever, daemon=True,
+        )
+        self._thread.start()
+        self._port = self._server.server_port
+
+    def tearDown(self):
+        self._server.shutdown()
+        self._server.server_close()
+        os.environ.pop("GIT_PROJECT_ROOT", None)
+        import shutil
+        shutil.rmtree(self._tmp, ignore_errors=True)
+
+    def _get_with_backend_response(self, cgi_response: bytes) -> int:
+        with mock.patch(
+            "bot_bottle.git_http_backend.subprocess.run",
+            return_value=mock.Mock(returncode=0, stdout=cgi_response),
+        ):
+            req = urllib.request.Request(
+                f"http://127.0.0.1:{self._port}/repo.git/info/refs",
+                method="GET",
+            )
+            try:
+                with urllib.request.urlopen(req, timeout=3) as resp:
+                    return resp.status
+            except urllib.error.HTTPError as e:  # type: ignore
+                return e.code
+
+    def test_empty_status_value_returns_500(self):
+        status = self._get_with_backend_response(
+            b"Status: \r\nContent-Type: text/plain\r\n\r\n"
+        )
+        self.assertEqual(500, status)
+
+    def test_non_numeric_status_returns_500(self):
+        status = self._get_with_backend_response(
+            b"Status: bad\r\nContent-Type: text/plain\r\n\r\n"
+        )
+        self.assertEqual(500, status)
+
+
 class TestContentLengthBounds(unittest.TestCase):
     """PRD 0041: malformed or oversized Content-Length is rejected before
     git http-backend is invoked."""

tests/unit/test_macos_container_util.py

@@ -73,6 +73,33 @@ resolver #2
         )
         self.assertTrue(run.call_args_list[-1].kwargs["check"])
 
+    def test_build_image_anchors_relative_dockerfile_to_context(self):
+        status = util.subprocess.CompletedProcess(
+            args=[],
+            returncode=0,
+            stdout=(
+                '[{"status":{"state":"running"},'
+                '"configuration":{"dns":{"nameservers":["9.9.9.9"]}}}]'
+            ),
+            stderr="",
+        )
+        with patch.object(util.subprocess, "run", return_value=status) as run, \
+             patch.object(util.os, "environ", {
+                 "BOT_BOTTLE_MACOS_CONTAINER_DNS": "9.9.9.9",
+             }):
+            util.build_image(
+                "bot-bottle-sidecars:latest",
+                "/repo",
+                dockerfile="Dockerfile.sidecars",
+            )
+        self.assertEqual(
+            [
+                "container", "build", "-t", "bot-bottle-sidecars:latest",
+                "--dns", "9.9.9.9", "-f", "/repo/Dockerfile.sidecars", "/repo",
+            ],
+            run.call_args_list[-1].args[0],
+        )
+
     def test_commit_container_execs_tar_and_builds_image(self):
         # stderr is bytes because subprocess.run uses stderr=PIPE without text=True
         completed = util.subprocess.CompletedProcess(

tests/unit/test_supervise_server.py

@@ -20,6 +20,7 @@ import supervise as _sv  # noqa: E402  # type: ignore
 
 from bot_bottle import supervise_server  # noqa: E402
 from bot_bottle.supervise_server import (
+    ERR_INTERNAL,
     ERR_INVALID_PARAMS,
     ERR_INVALID_REQUEST,
     ERR_METHOD_NOT_FOUND,
@@ -29,7 +30,9 @@ from bot_bottle.supervise_server import (
     PROPOSED_FILE_FIELD,
     ServerConfig,
     TOOL_DEFINITIONS,
+    _RpcClientError,
     _RpcError,
+    _RpcInternalError,
     _response_timeout_from_env,
     format_response_text,
     handle_initialize,
@@ -77,6 +80,65 @@ class TestValidation(unittest.TestCase):
         self.assertIn("must not change egress logging", cm.exception.message)
 
 
+# --- Error taxonomy --------------------------------------------------------
+
+
+class TestRpcErrorTaxonomy(unittest.TestCase):
+    def test_rpc_client_error_is_rpc_error(self):
+        e = _RpcClientError(ERR_INVALID_PARAMS, "bad param")
+        self.assertIsInstance(e, _RpcError)
+        self.assertEqual(ERR_INVALID_PARAMS, e.code)
+        self.assertEqual("bad param", e.message)
+
+    def test_rpc_internal_error_is_rpc_error(self):
+        e = _RpcInternalError("disk full")
+        self.assertIsInstance(e, _RpcError)
+        self.assertEqual(ERR_INTERNAL, e.code)
+        self.assertEqual("disk full", e.message)
+
+    def test_rpc_internal_error_preserves_cause(self):
+        cause = OSError("no space left on device")
+        try:
+            raise _RpcInternalError("failed to write") from cause
+        except _RpcInternalError as e:
+            self.assertIs(cause, e.__cause__)
+
+    def test_parse_error_is_client_error(self):
+        with self.assertRaises(_RpcClientError):
+            parse_jsonrpc(b"{bad json")
+
+    def test_validation_error_is_client_error(self):
+        with self.assertRaises(_RpcClientError):
+            validate_proposed_file(_sv.TOOL_EGRESS_ALLOW, "routes: nope\n")
+
+    def test_unknown_tool_in_tools_call_is_client_error(self):
+        config = ServerConfig(bottle_slug="dev", queue_dir=Path("/unused"))
+        with self.assertRaises(_RpcClientError) as cm:
+            handle_tools_call({"name": "no-such-tool", "arguments": {}}, config)
+        self.assertEqual(ERR_INVALID_PARAMS, cm.exception.code)
+
+
+class TestRpcInternalErrorOnIoFailure(unittest.TestCase):
+    def test_write_proposal_os_error_raises_internal(self):
+        config = ServerConfig(
+            bottle_slug="dev",
+            queue_dir=Path("/dev/null/cannot-exist"),
+        )
+        with self.assertRaises(_RpcInternalError) as cm:
+            handle_tools_call(
+                {
+                    "name": _sv.TOOL_CAPABILITY_BLOCK,
+                    "arguments": {
+                        "dockerfile": "FROM python:3.13\n",
+                        "justification": "x",
+                    },
+                },
+                config,
+            )
+        self.assertEqual(ERR_INTERNAL, cm.exception.code)
+        self.assertIsNotNone(cm.exception.__cause__)
+
+
 # --- JSON-RPC parsing ------------------------------------------------------
 
 
@@ -469,6 +531,26 @@ class TestHttpEndToEnd(unittest.TestCase):
         )
         self.assertEqual(ERR_METHOD_NOT_FOUND, result["error"]["code"])  # type: ignore[index]
 
+    def test_internal_error_returns_err_internal_over_http(self):
+        with patch.object(
+            supervise_server._sv, "write_proposal",
+            side_effect=OSError("disk full"),
+        ):
+            result = self._post_jsonrpc({
+                "jsonrpc": "2.0",
+                "id": 99,
+                "method": "tools/call",
+                "params": {
+                    "name": _sv.TOOL_CAPABILITY_BLOCK,
+                    "arguments": {
+                        "dockerfile": "FROM python:3.13\n",
+                        "justification": "x",
+                    },
+                },
+            })
+        self.assertIn("error", result)
+        self.assertEqual(ERR_INTERNAL, result["error"]["code"])  # type: ignore[index]
+
     def test_health_endpoint(self):
         conn = http.client.HTTPConnection("127.0.0.1", self.port, timeout=5)
         try: