diff --git a/projects/jdwp/tools/check_command_ids_order.py b/projects/jdwp/tools/check_command_ids_order.py
new file mode 100644
index 0000000..dccc08f
--- /dev/null
+++ b/projects/jdwp/tools/check_command_ids_order.py
@@ -0,0 +1,51 @@
+from argparse import ArgumentParser
+import os
+from projects.jdwp.defs.schema import CommandSet
+
+
+def check_command_ids(command_set: CommandSet) -> None:
+    """Verifies if command IDs in a command set are in ascending order."""
+    sorted_command_ids = [command.id for command in command_set.commands]
+    if sorted_command_ids != sorted(sorted_command_ids):
+        raise ValueError(
+            f"Command IDs in {command_set.name} are NOT in ascending order."
+        )
+
+
+def handle_file_error(file_path: str, e: Exception) -> None:
+    """Handles errors related to loading a command set file."""
+    print(f"Error loading file: {file_path} ({e})")
+    exit(1)
+
+
+def main() -> None:
+    parser = ArgumentParser(description="Check command IDs in command sets")
+    parser.add_argument("--verbose", action="store_true", help="Enable verbose output")
+    parser.add_argument(
+        "command_sets_dir", type=str, help="Directory containing command set files"
+    )
+    args = parser.parse_args()
+
+    command_sets_dir = os.path.abspath(args.command_sets_dir)
+    command_set_files = [f for f in os.listdir(command_sets_dir) if f.endswith(".py")]
+
+    for file in command_set_files:
+        try:
+            module_name = os.path.splitext(file)[0]
+            module_name_title = module_name.replace("_", " ").title().replace(" ", "")
+            module = __import__(
+                f"projects.jdwp.defs.command_sets.{module_name}", fromlist=[module_name]
+            )
+
+            if args.verbose:
+                print(f"Checking {module_name_title}...")
+
+            if any(isinstance(obj, CommandSet) for obj in vars(module).values()):
+                command_set = getattr(module, module_name_title)
+                check_command_ids(command_set)
+        except Exception as e:
+            handle_file_error(file, e)
+
+
+if __name__ == "__main__":
+    main()
diff --git a/projects/jdwp/tools/check_union_types.py b/projects/jdwp/tools/check_union_types.py
new file mode 100644
index 0000000..42ec00c
--- /dev/null
+++ b/projects/jdwp/tools/check_union_types.py
@@ -0,0 +1,107 @@
+import argparse
+import os
+from projects.jdwp.defs.constants import ModifierKind
+from projects.jdwp.defs.command_sets.event_request import (
+    CountModifier,
+    ConditionalModifier,
+    ThreadOnlyModifier,
+    ClassOnlyModifier,
+    ClassMatchModifier,
+    ClassExcludeModifier,
+    StepModifier,
+    LocationOnlyModifier,
+    ExceptionOnlyModifier,
+    FieldOnlyModifier,
+    InstanceOnlyModifier,
+    SourceNameMatchModifier,
+)
+from projects.jdwp.defs.schema import CommandSet, TaggedUnion, UnionTag, Array, Struct
+
+
+def expected_case_value_for_modifier_kind(modifier_kind: ModifierKind) -> Struct:
+    if modifier_kind == ModifierKind.COUNT:
+        return CountModifier
+    elif modifier_kind == ModifierKind.CONDITIONAL:
+        return ConditionalModifier
+    elif modifier_kind == ModifierKind.THREAD_ONLY:
+        return ThreadOnlyModifier
+    elif modifier_kind == ModifierKind.CLASS_ONLY:
+        return ClassOnlyModifier
+    elif modifier_kind == ModifierKind.CLASS_MATCH:
+        return ClassMatchModifier
+    elif modifier_kind == ModifierKind.CLASS_EXCLUDE:
+        return ClassExcludeModifier
+    elif modifier_kind == ModifierKind.STEP:
+        return StepModifier
+    elif modifier_kind == ModifierKind.LOCATION_ONLY:
+        return LocationOnlyModifier
+    elif modifier_kind == ModifierKind.EXCEPTION_ONLY:
+        return ExceptionOnlyModifier
+    elif modifier_kind == ModifierKind.FIELD_ONLY:
+        return FieldOnlyModifier
+    elif modifier_kind == ModifierKind.INSTANCE_ONLY:
+        return InstanceOnlyModifier
+    elif modifier_kind == ModifierKind.SOURCE_NAME_MATCH:
+        return SourceNameMatchModifier
+    else:
+        raise ValueError(f"Unknown modifierKind: {modifier_kind}")
+
+
+def check_tagged_union_mappings(command_set: CommandSet) -> None:
+    for command in command_set.commands:
+        if command.out is None:
+            continue
+
+        for field in command.out.fields:
+            mod_kind_value = None
+
+            if isinstance(field.type, Array):
+                for element in field.type.element_type.fields:
+                    if isinstance(element.type, UnionTag):
+                        mod_kind_value = element.type.value
+                    if isinstance(element.type, TaggedUnion):
+                        union_tag: UnionTag = element.type.tag
+                        union_cases: dict = element.type.cases
+                        if union_tag.type.value != mod_kind_value:
+                            print(
+                                f"Error in command '{command.name}': Invalid union tag for field '{field.name}'."
+                            )
+                            exit(1)
+                        for case_value, case_type in union_cases.items():
+                            expected_case_value = expected_case_value_for_modifier_kind(
+                                case_value
+                            )
+                            if expected_case_value != case_type:
+                                print(
+                                    f"Error in command '{command.name}': Invalid case type for field '{field.name}'."
+                                )
+                                exit(1)
+
+
+def main() -> None:
+    parser = argparse.ArgumentParser(
+        description="Check tagged union mappings in command sets"
+    )
+    parser.add_argument(
+        "command_sets_dir", type=str, help="Directory containing command set files"
+    )
+    args = parser.parse_args()
+
+    command_sets_dir: str = args.command_sets_dir
+    for file in os.listdir(command_sets_dir):
+        if file.endswith(".py"):
+            module_name: str = os.path.splitext(file)[0]
+            module_name_title: str = (
+                module_name.replace("_", " ").title().replace(" ", "")
+            )
+            module = __import__(
+                f"projects.jdwp.defs.command_sets.{module_name}", fromlist=[module_name]
+            )
+
+            command_set: CommandSet = getattr(module, module_name_title)
+            if isinstance(command_set, CommandSet):
+                check_tagged_union_mappings(command_set)
+
+
+if __name__ == "__main__":
+    main()