diff --git a/pkgs/clan-cli/tests/test_api_dataclass_compat.py b/pkgs/clan-cli/tests/test_api_dataclass_compat.py
new file mode 100644
index 000000000..2a5683598
--- /dev/null
+++ b/pkgs/clan-cli/tests/test_api_dataclass_compat.py
@@ -0,0 +1,125 @@
+import ast
+import importlib.util
+import os
+import sys
+from dataclasses import is_dataclass
+from pathlib import Path
+
+from clan_cli.api.util import type_to_dict
+from clan_cli.errors import ClanError
+
+
+def find_dataclasses_in_directory(
+    directory: Path, exclude_paths: list[str] = []
+) -> list[tuple[str, str]]:
+    """
+    Find all dataclass classes in all Python files within a nested directory.
+
+    Args:
+        directory (str): The root directory to start searching from.
+
+    Returns:
+        List[Tuple[str, str]]: A list of tuples containing the file path and the dataclass name.
+    """
+    dataclass_files = []
+
+    excludes = [os.path.join(directory, d) for d in exclude_paths]
+
+    for root, _, files in os.walk(directory, topdown=False):
+        for file in files:
+            if not file.endswith(".py"):
+                continue
+
+            file_path = os.path.join(root, file)
+
+            if file_path in excludes:
+                print(f"Skipping dataclass check for file: {file_path}")
+                continue
+
+            with open(file_path, encoding="utf-8") as f:
+                try:
+                    tree = ast.parse(f.read(), filename=file_path)
+                    for node in ast.walk(tree):
+                        if isinstance(node, ast.ClassDef):
+                            for deco in node.decorator_list:
+                                if (
+                                    isinstance(deco, ast.Name)
+                                    and deco.id == "dataclass"
+                                ):
+                                    dataclass_files.append((file_path, node.name))
+                                elif (
+                                    isinstance(deco, ast.Call)
+                                    and isinstance(deco.func, ast.Name)
+                                    and deco.func.id == "dataclass"
+                                ):
+                                    dataclass_files.append((file_path, node.name))
+                except (SyntaxError, UnicodeDecodeError) as e:
+                    print(f"Error parsing {file_path}: {e}")
+
+    return dataclass_files
+
+
+def load_dataclass_from_file(
+    file_path: str, class_name: str, root_dir: str
+) -> type | None:
+    """
+    Load a dataclass from a given file path.
+
+    Args:
+        file_path (str): Path to the file.
+        class_name (str): Name of the class to load.
+
+    Returns:
+        List[Type]: The dataclass type if found, else an empty list.
+    """
+    module_name = (
+        os.path.relpath(file_path, root_dir).replace(os.path.sep, ".").rstrip(".py")
+    )
+    # spec = importlib.util.spec_from_file_location(module_name, file_path)
+    # module = importlib.util.module_from_spec(spec)
+    # spec.loader.exec_module(module)
+    # breakpoint()
+    try:
+        sys.path.insert(0, root_dir)
+        spec = importlib.util.spec_from_file_location(module_name, file_path)
+        if not spec:
+            raise ClanError(f"Could not load spec from file: {file_path}")
+
+        module = importlib.util.module_from_spec(spec)
+        if not module:
+            raise ClanError(f"Could not create module: {file_path}")
+
+        if not spec.loader:
+            raise ClanError(f"Could not load loader from spec: {spec}")
+
+        spec.loader.exec_module(module)
+
+    finally:
+        sys.path.pop(0)
+    dataclass_type = getattr(module, class_name, None)
+
+    if dataclass_type and is_dataclass(dataclass_type):
+        return dataclass_type
+    return None
+
+
+def test_all_dataclasses() -> None:
+    # Excludes:
+    # - API includes Type Generic wrappers, that are not known in the init file.
+    excludes = ["api/__init__.py"]
+
+    cli_path = Path("clan_cli").resolve()
+    dataclasses = find_dataclasses_in_directory(cli_path, excludes)
+
+    for file, dataclass in dataclasses:
+        print(f"Found dataclass {dataclass} in {file}")
+        # The parent directory of the clan_cli is the projects root directory
+        try:
+            dclass = load_dataclass_from_file(file, dataclass, str(cli_path.parent))
+            json_schema = type_to_dict(dclass, scope=f"FILE {file} {dataclass}")
+        except Exception as e:
+            print(f"Error loading dataclass {dataclass} from {file}: {e}")
+            raise ClanError(
+                f"Error loading dataclass {dataclass} from {file}: {e}",
+                location=__file__,
+            )