diff --git a/src/claude_agent_sdk/__init__.py b/src/claude_agent_sdk/__init__.py
index 4898bc0b..07a3ff25 100644
--- a/src/claude_agent_sdk/__init__.py
+++ b/src/claude_agent_sdk/__init__.py
@@ -10,6 +10,7 @@
     CLIJSONDecodeError,
     CLINotFoundError,
     ProcessError,
+    SandboxFileWatcherError,
 )
 from ._internal.transport import Transport
 from ._version import __version__
@@ -362,4 +363,5 @@ async def call_tool(name: str, arguments: dict[str, Any]) -> Any:
     "CLINotFoundError",
     "ProcessError",
     "CLIJSONDecodeError",
+    "SandboxFileWatcherError",
 ]
diff --git a/src/claude_agent_sdk/_errors.py b/src/claude_agent_sdk/_errors.py
index c86bf235..e0fbc36a 100644
--- a/src/claude_agent_sdk/_errors.py
+++ b/src/claude_agent_sdk/_errors.py
@@ -54,3 +54,26 @@ class MessageParseError(ClaudeSDKError):
     def __init__(self, message: str, data: dict[str, Any] | None = None):
         self.data = data
         super().__init__(message)
+
+
+class SandboxFileWatcherError(ClaudeSDKError):
+    """Raised when the CLI's sandbox file watcher fails.
+
+    This typically happens on macOS when the sandbox tries to watch
+    system temp directories containing socket files or other unwatchable
+    file types. The CLI's file watcher throws EOPNOTSUPP or EINTR errors
+    on these files.
+    """
+
+    def __init__(self, path: str, error_code: str):
+        self.path = path
+        self.error_code = error_code
+        message = (
+            f"Sandbox file watcher failed on '{path}' ({error_code}). "
+            "This is a known issue with the Claude CLI's sandbox on macOS. "
+            "The sandbox tries to watch system temp directories that contain "
+            "socket files (from VSCode, Docker, etc.) which cannot be watched. "
+            "Workarounds: 1) Disable sandbox (sandbox=None), "
+            "2) Run in a container with a clean /tmp directory."
+        )
+        super().__init__(message)
diff --git a/src/claude_agent_sdk/_internal/transport/subprocess_cli.py b/src/claude_agent_sdk/_internal/transport/subprocess_cli.py
index a4882db1..875663c2 100644
--- a/src/claude_agent_sdk/_internal/transport/subprocess_cli.py
+++ b/src/claude_agent_sdk/_internal/transport/subprocess_cli.py
@@ -20,7 +20,12 @@
 from anyio.abc import Process
 from anyio.streams.text import TextReceiveStream, TextSendStream
 
-from ..._errors import CLIConnectionError, CLINotFoundError, ProcessError
+from ..._errors import (
+    CLIConnectionError,
+    CLINotFoundError,
+    ProcessError,
+    SandboxFileWatcherError,
+)
 from ..._errors import CLIJSONDecodeError as SDKJSONDecodeError
 from ..._version import __version__
 from ...types import ClaudeAgentOptions
@@ -66,6 +71,9 @@ def __init__(
         )
         self._temp_files: list[str] = []  # Track temporary files for cleanup
         self._write_lock: anyio.Lock = anyio.Lock()
+        # Track sandbox file watcher errors from stderr
+        self._sandbox_watcher_error: SandboxFileWatcherError | None = None
+        self._sandbox_watcher_error_event: anyio.Event | None = None
 
     def _find_cli(self) -> str:
         """Find Claude Code CLI binary."""
@@ -391,12 +399,24 @@ async def connect(self) -> None:
             if self._cwd:
                 process_env["PWD"] = self._cwd
 
-            # Pipe stderr if we have a callback OR debug mode is enabled
+            # Check if sandbox is enabled - we need stderr to detect file watcher errors
+            sandbox_enabled = (
+                self._options.sandbox is not None
+                and self._options.sandbox.get("enabled", False)
+            )
+
+            # Pipe stderr if we have a callback, debug mode, or sandbox is enabled
+            # (sandbox needs stderr to detect file watcher errors)
             should_pipe_stderr = (
                 self._options.stderr is not None
                 or "debug-to-stderr" in self._options.extra_args
+                or sandbox_enabled
             )
 
+            # Initialize event for sandbox error detection
+            if sandbox_enabled:
+                self._sandbox_watcher_error_event = anyio.Event()
+
             # For backward compat: use debug_stderr file object if no callback and debug is on
             stderr_dest = PIPE if should_pipe_stderr else None
 
@@ -446,6 +466,13 @@ async def connect(self) -> None:
             self._exit_error = error
             raise error from e
 
+    # Regex pattern to detect sandbox file watcher errors from CLI stderr
+    # Matches: "EOPNOTSUPP: unknown error, watch '/path/...'"
+    #          "EINTR: interrupted system call, watch '/path/...'"
+    _SANDBOX_WATCHER_ERROR_PATTERN = re.compile(
+        r"(EOPNOTSUPP|EINTR):[^,]+,\s*watch\s+'([^']+)'"
+    )
+
     async def _handle_stderr(self) -> None:
         """Handle stderr stream - read and invoke callbacks."""
         if not self._stderr_stream:
@@ -457,6 +484,25 @@ async def _handle_stderr(self) -> None:
                 if not line_str:
                     continue
 
+                # Check for sandbox file watcher errors
+                match = self._SANDBOX_WATCHER_ERROR_PATTERN.search(line_str)
+                if match and self._sandbox_watcher_error is None:
+                    error_code = match.group(1)
+                    path = match.group(2)
+                    self._sandbox_watcher_error = SandboxFileWatcherError(
+                        path=path, error_code=error_code
+                    )
+                    logger.error(
+                        f"Sandbox file watcher error detected: {error_code} on {path}"
+                    )
+                    # Signal any waiters that an error occurred
+                    if self._sandbox_watcher_error_event:
+                        self._sandbox_watcher_error_event.set()
+                    # Terminate the process since it will hang
+                    if self._process and self._process.returncode is None:
+                        with suppress(ProcessLookupError):
+                            self._process.terminate()
+
                 # Call the stderr callback if provided
                 if self._options.stderr:
                     self._options.stderr(line_str)
@@ -569,6 +615,10 @@ async def _read_messages_impl(self) -> AsyncIterator[dict[str, Any]]:
         # Process stdout messages
         try:
             async for line in self._stdout_stream:
+                # Check for sandbox file watcher error before processing
+                if self._sandbox_watcher_error is not None:
+                    raise self._sandbox_watcher_error
+
                 line_str = line.strip()
                 if not line_str:
                     continue
@@ -612,6 +662,10 @@ async def _read_messages_impl(self) -> AsyncIterator[dict[str, Any]]:
             # Client disconnected
             pass
 
+        # Check for sandbox file watcher error after reading
+        if self._sandbox_watcher_error is not None:
+            raise self._sandbox_watcher_error
+
         # Check process completion and handle errors
         try:
             returncode = await self._process.wait()
@@ -620,6 +674,9 @@ async def _read_messages_impl(self) -> AsyncIterator[dict[str, Any]]:
 
         # Use exit code for error detection
         if returncode is not None and returncode != 0:
+            # Check if it was due to a sandbox file watcher error
+            if self._sandbox_watcher_error is not None:
+                raise self._sandbox_watcher_error
             self._exit_error = ProcessError(
                 f"Command failed with exit code {returncode}",
                 exit_code=returncode,
diff --git a/tests/test_errors.py b/tests/test_errors.py
index 9490d075..f7cfcb4d 100644
--- a/tests/test_errors.py
+++ b/tests/test_errors.py
@@ -6,6 +6,7 @@
     CLIJSONDecodeError,
     CLINotFoundError,
     ProcessError,
+    SandboxFileWatcherError,
 )
 
 
@@ -50,3 +51,17 @@ def test_json_decode_error(self):
             assert error.line == "{invalid json}"
             assert error.original_error == e
             assert "Failed to decode JSON" in str(error)
+
+    def test_sandbox_file_watcher_error(self):
+        """Test SandboxFileWatcherError."""
+        error = SandboxFileWatcherError(
+            path="/var/folders/abc/T/vscode-git-123.sock",
+            error_code="EOPNOTSUPP"
+        )
+        assert isinstance(error, ClaudeSDKError)
+        assert error.path == "/var/folders/abc/T/vscode-git-123.sock"
+        assert error.error_code == "EOPNOTSUPP"
+        assert "Sandbox file watcher failed" in str(error)
+        assert "vscode-git-123.sock" in str(error)
+        assert "EOPNOTSUPP" in str(error)
+        assert "socket files" in str(error)  # Helpful message
diff --git a/tests/test_transport.py b/tests/test_transport.py
index fe9b6b22..5dc1159b 100644
--- a/tests/test_transport.py
+++ b/tests/test_transport.py
@@ -826,3 +826,33 @@ async def do_write(i: int):
                 await process.wait()
 
         anyio.run(_test, backend="trio")
+
+    def test_sandbox_watcher_error_pattern_detection(self):
+        """Test that sandbox file watcher error patterns are correctly detected."""
+        transport = SubprocessCLITransport(
+            prompt="test",
+            options=make_options(sandbox={"enabled": True}),
+        )
+
+        # Test EOPNOTSUPP error pattern
+        pattern = transport._SANDBOX_WATCHER_ERROR_PATTERN
+
+        # Test cases that should match
+        eopnotsupp_line = "EOPNOTSUPP: unknown error, watch '/var/folders/abc/T/vscode-git-123.sock'"
+        match = pattern.search(eopnotsupp_line)
+        assert match is not None
+        assert match.group(1) == "EOPNOTSUPP"
+        assert match.group(2) == "/var/folders/abc/T/vscode-git-123.sock"
+
+        eintr_line = "EINTR: interrupted system call, watch '/var/folders/pq/9xtx/T/python-test-discovery-5c4f'"
+        match = pattern.search(eintr_line)
+        assert match is not None
+        assert match.group(1) == "EINTR"
+        assert match.group(2) == "/var/folders/pq/9xtx/T/python-test-discovery-5c4f"
+
+        # Test cases that should NOT match
+        normal_error = "Error: Something went wrong"
+        assert pattern.search(normal_error) is None
+
+        other_syscall = "ENOENT: no such file or directory, open '/path/to/file'"
+        assert pattern.search(other_syscall) is None