diff --git a/src/deepwork/core/command_executor.py b/src/deepwork/core/command_executor.py
index 629b4f50..74288a13 100644
--- a/src/deepwork/core/command_executor.py
+++ b/src/deepwork/core/command_executor.py
@@ -159,15 +159,32 @@ def all_commands_succeeded(results: list[CommandResult]) -> bool:
     return all(r.success for r in results)
 
 
-def format_command_errors(results: list[CommandResult]) -> str:
-    """Format error messages from failed commands."""
+def format_command_errors(
+    results: list[CommandResult],
+    rule_name: str | None = None,
+) -> str:
+    """Format detailed error messages from failed commands.
+
+    Args:
+        results: List of command execution results
+        rule_name: Optional rule name to include in error message
+
+    Returns:
+        Formatted error message with command, exit code, stdout, and stderr
+    """
     errors: list[str] = []
     for result in results:
         if not result.success:
-            msg = f"Command failed: {result.command}\n"
-            if result.stderr:
-                msg += f"Error: {result.stderr}\n"
-            if result.exit_code != 0:
-                msg += f"Exit code: {result.exit_code}\n"
-            errors.append(msg)
-    return "\n".join(errors)
+            parts: list[str] = []
+            if rule_name:
+                parts.append(f"Rule: {rule_name}")
+            parts.append(f"Command: {result.command}")
+            parts.append(f"Exit code: {result.exit_code}")
+            if result.stdout and result.stdout.strip():
+                parts.append(f"Stdout:\n{result.stdout.strip()}")
+            if result.stderr and result.stderr.strip():
+                parts.append(f"Stderr:\n{result.stderr.strip()}")
+            if not result.stdout.strip() and not result.stderr.strip():
+                parts.append("(no output)")
+            errors.append("\n".join(parts))
+    return "\n\n".join(errors)
diff --git a/src/deepwork/hooks/rules_check.py b/src/deepwork/hooks/rules_check.py
index 024b94ad..3d71dcce 100644
--- a/src/deepwork/hooks/rules_check.py
+++ b/src/deepwork/hooks/rules_check.py
@@ -654,10 +654,10 @@ def rules_check_hook(hook_input: HookInput) -> HookOutput:
                             ),
                         )
                     else:
-                        # Command failed
-                        error_msg = format_command_errors(cmd_results)
-                        skip_hint = f"To skip, include `<promise>✓ {rule.name}</promise>` in your response.\n"
-                        command_errors.append(f"## {rule.name}\n{error_msg}{skip_hint}")
+                        # Command failed - format detailed error message
+                        error_msg = format_command_errors(cmd_results, rule_name=rule.name)
+                        skip_hint = f"\nTo skip, include `<promise>✓ {rule.name}</promise>` in your response."
+                        command_errors.append(f"{error_msg}{skip_hint}")
                         queue.update_status(
                             trigger_hash,
                             QueueEntryStatus.FAILED,
@@ -694,17 +694,33 @@ def rules_check_hook(hook_input: HookInput) -> HookOutput:
 
 def main() -> None:
     """Entry point for the rules check hook."""
-    # Determine platform from environment
     platform_str = os.environ.get("DEEPWORK_HOOK_PLATFORM", "claude")
     try:
         platform = Platform(platform_str)
     except ValueError:
         platform = Platform.CLAUDE
 
-    # Run the hook with the wrapper
     exit_code = run_hook(rules_check_hook, platform)
     sys.exit(exit_code)
 
 
 if __name__ == "__main__":
-    main()
+    # Wrap entry point to catch early failures (e.g., import errors in wrapper.py)
+    try:
+        main()
+    except Exception as e:
+        # Last resort error handling - output JSON manually since wrapper may be broken
+        import json
+        import traceback
+
+        error_output = {
+            "decision": "block",
+            "reason": (
+                "## Hook Script Error\n\n"
+                f"Error type: {type(e).__name__}\n"
+                f"Error: {e}\n\n"
+                f"Traceback:\n```\n{traceback.format_exc()}\n```"
+            ),
+        }
+        print(json.dumps(error_output))
+        sys.exit(0)
diff --git a/src/deepwork/hooks/wrapper.py b/src/deepwork/hooks/wrapper.py
index ef20899c..96dba3a9 100644
--- a/src/deepwork/hooks/wrapper.py
+++ b/src/deepwork/hooks/wrapper.py
@@ -321,6 +321,55 @@ def write_stdout(data: str) -> None:
     print(data)
 
 
+def format_hook_error(
+    error: Exception,
+    context: str = "",
+) -> dict[str, Any]:
+    """
+    Format an error into a blocking JSON response with detailed information.
+
+    This is used when the hook script itself fails, to provide useful
+    error information to the user instead of a generic "non-blocking status code" message.
+
+    Args:
+        error: The exception that occurred
+        context: Additional context about where the error occurred
+
+    Returns:
+        Dict with decision="block" and detailed error message
+    """
+    import traceback
+
+    error_type = type(error).__name__
+    error_msg = str(error)
+    tb = traceback.format_exc()
+
+    parts = ["## Hook Script Error", ""]
+    if context:
+        parts.append(f"Context: {context}")
+    parts.append(f"Error type: {error_type}")
+    parts.append(f"Error: {error_msg}")
+    parts.append("")
+    parts.append("Traceback:")
+    parts.append(f"```\n{tb}\n```")
+
+    return {
+        "decision": "block",
+        "reason": "\n".join(parts),
+    }
+
+
+def output_hook_error(error: Exception, context: str = "") -> None:
+    """
+    Output a hook error as JSON to stdout.
+
+    Use this in exception handlers to ensure the hook always outputs
+    valid JSON even when crashing.
+    """
+    error_dict = format_hook_error(error, context)
+    print(json.dumps(error_dict))
+
+
 def run_hook(
     hook_fn: Callable[[HookInput], HookOutput],
     platform: Platform,
@@ -340,24 +389,25 @@ def run_hook(
         platform: The platform calling this hook
 
     Returns:
-        Exit code (0 for success, 2 for blocking)
+        Exit code (0 for success)
     """
-    # Read and normalize input
-    raw_input = read_stdin()
-    hook_input = normalize_input(raw_input, platform)
-
-    # Call the hook
     try:
+        # Read and normalize input
+        raw_input = read_stdin()
+        hook_input = normalize_input(raw_input, platform)
+
+        # Call the hook
         hook_output = hook_fn(hook_input)
-    except Exception as e:
-        # On error, allow the action but log
-        print(f"Hook error: {e}", file=sys.stderr)
-        hook_output = HookOutput()
 
-    # Denormalize and write output
-    output_json = denormalize_output(hook_output, platform, hook_input.event)
-    write_stdout(output_json)
+        # Denormalize and write output
+        output_json = denormalize_output(hook_output, platform, hook_input.event)
+        write_stdout(output_json)
 
-    # Always return 0 when using JSON output format
-    # The decision field in the JSON controls blocking behavior
-    return 0
+        # Always return 0 when using JSON output format
+        # The decision field in the JSON controls blocking behavior
+        return 0
+
+    except Exception as e:
+        # On any error, output a proper JSON error response
+        output_hook_error(e, context=f"Running hook {hook_fn.__name__}")
+        return 0  # Return 0 so Claude Code processes our JSON output
diff --git a/tests/unit/test_command_executor.py b/tests/unit/test_command_executor.py
index 77d7b320..12472729 100644
--- a/tests/unit/test_command_executor.py
+++ b/tests/unit/test_command_executor.py
@@ -170,7 +170,7 @@ def test_single_error(self) -> None:
             ),
         ]
         output = format_command_errors(results)
-        assert "failing_cmd" in output
+        assert "Command: failing_cmd" in output
         assert "Something went wrong" in output
         assert "Exit code: 1" in output
 
@@ -195,3 +195,70 @@ def test_ignores_success(self) -> None:
         output = format_command_errors(results)
         assert "good_cmd" not in output
         assert "bad_cmd" in output
+
+    def test_includes_rule_name(self) -> None:
+        """Include rule name when provided."""
+        results = [
+            CommandResult(
+                success=False,
+                exit_code=1,
+                stdout="",
+                stderr="Error output",
+                command="test_cmd",
+            ),
+        ]
+        output = format_command_errors(results, rule_name="My Test Rule")
+        assert "Rule: My Test Rule" in output
+        assert "Command: test_cmd" in output
+        assert "Exit code: 1" in output
+        assert "Stderr:\nError output" in output
+
+    def test_includes_stdout(self) -> None:
+        """Include stdout when present."""
+        results = [
+            CommandResult(
+                success=False,
+                exit_code=1,
+                stdout="Standard output here",
+                stderr="Standard error here",
+                command="test_cmd",
+            ),
+        ]
+        output = format_command_errors(results)
+        assert "Stdout:\nStandard output here" in output
+        assert "Stderr:\nStandard error here" in output
+
+    def test_shows_no_output_message(self) -> None:
+        """Show '(no output)' when no stdout or stderr."""
+        results = [
+            CommandResult(
+                success=False,
+                exit_code=42,
+                stdout="",
+                stderr="",
+                command="silent_cmd",
+            ),
+        ]
+        output = format_command_errors(results)
+        assert "Command: silent_cmd" in output
+        assert "Exit code: 42" in output
+        assert "(no output)" in output
+
+    def test_full_error_format(self) -> None:
+        """Test complete error format with all fields."""
+        results = [
+            CommandResult(
+                success=False,
+                exit_code=42,
+                stdout="stdout output",
+                stderr="stderr output",
+                command="echo test && exit 42",
+            ),
+        ]
+        output = format_command_errors(results, rule_name="Command Failure Rule")
+        # Verify all parts are present in the correct format
+        assert "Rule: Command Failure Rule" in output
+        assert "Command: echo test && exit 42" in output
+        assert "Exit code: 42" in output
+        assert "Stdout:\nstdout output" in output
+        assert "Stderr:\nstderr output" in output
diff --git a/tests/unit/test_hook_wrapper.py b/tests/unit/test_hook_wrapper.py
index fd1a51d9..a0c84df6 100644
--- a/tests/unit/test_hook_wrapper.py
+++ b/tests/unit/test_hook_wrapper.py
@@ -32,7 +32,10 @@
     NormalizedEvent,
     Platform,
     denormalize_output,
+    format_hook_error,
     normalize_input,
+    output_hook_error,
+    run_hook,
 )
 
 
@@ -555,3 +558,76 @@ def sample_hook(hook_input: HookInput) -> HookOutput:
         assert claude_result["decision"] == "block"
         assert gemini_result["decision"] == "deny"
         assert claude_result["reason"] == gemini_result["reason"]
+
+
+class TestHookErrorHandling:
+    """Tests for hook script error handling.
+
+    When a hook script crashes, it should output valid JSON with detailed
+    error information rather than causing a generic "non-blocking status code" error.
+    """
+
+    def test_format_hook_error_basic(self) -> None:
+        """Test that format_hook_error produces blocking JSON with error details."""
+
+        error = ValueError("Something went wrong")
+        result = format_hook_error(error)
+
+        assert result["decision"] == "block"
+        assert "ValueError" in result["reason"]
+        assert "Something went wrong" in result["reason"]
+        assert "Traceback" in result["reason"]
+
+    def test_format_hook_error_with_context(self) -> None:
+        """Test that format_hook_error includes context when provided."""
+
+        error = RuntimeError("Test error")
+        result = format_hook_error(error, context="Loading rules")
+
+        assert result["decision"] == "block"
+        assert "Loading rules" in result["reason"]
+        assert "RuntimeError" in result["reason"]
+        assert "Test error" in result["reason"]
+
+    def test_format_hook_error_includes_traceback(self) -> None:
+        """Test that format_hook_error includes the full traceback."""
+
+        try:
+            raise KeyError("missing_key")
+        except KeyError as e:
+            result = format_hook_error(e)
+
+        assert "Traceback" in result["reason"]
+        assert "KeyError" in result["reason"]
+        assert "missing_key" in result["reason"]
+
+    def test_output_hook_error_produces_json(self, capsys: object) -> None:
+        """Test that output_hook_error writes valid JSON to stdout."""
+
+        error = TypeError("Type mismatch")
+        output_hook_error(error, context="test context")
+
+        captured = capsys.readouterr()  # type: ignore[attr-defined]
+        result = json.loads(captured.out.strip())
+
+        assert result["decision"] == "block"
+        assert "TypeError" in result["reason"]
+        assert "test context" in result["reason"]
+
+    def test_run_hook_catches_hook_function_errors(self, capsys: object) -> None:
+        """Test that run_hook outputs JSON when hook function raises an exception."""
+        from deepwork.hooks.wrapper import HookInput, HookOutput, Platform
+
+        def failing_hook(hook_input: HookInput) -> HookOutput:
+            raise RuntimeError("Hook crashed!")
+
+        exit_code = run_hook(failing_hook, Platform.CLAUDE)
+
+        captured = capsys.readouterr()  # type: ignore[attr-defined]
+        result = json.loads(captured.out.strip())
+
+        assert exit_code == 0  # Should return 0 so JSON is processed
+        assert result["decision"] == "block"
+        assert "RuntimeError" in result["reason"]
+        assert "Hook crashed!" in result["reason"]
+        assert "failing_hook" in result["reason"]  # Context includes function name