diff --git a/ci/generate_checked_functions.py b/ci/generate_checked_functions.py
index 572d94646..f682fd676 100644
--- a/ci/generate_checked_functions.py
+++ b/ci/generate_checked_functions.py
@@ -2,10 +2,78 @@ from pycparser import c_parser, c_ast, parse_file
 import os
 
 
-# Updated generate_checked_function to dynamically update Result definition for new return types
+def collect_typedefs(ast):
+    """Collect all typedefs in the AST."""
+    typedefs = {}
+    for node in ast.ext:
+        if not isinstance(node, c_ast.Typedef):
+            continue
+
+        typedef_name = node.name
+        typedef_type = node.type
+        typedefs[typedef_name] = typedef_type
+    return typedefs
 
 
-def generate_checked_function(func):
+def resolve_typedef(typedefs, type_name):
+    """Resolve a typedef to its underlying type."""
+
+    def resolve_base_type(ptr_decl):
+        # handle cases like: typedef int******* ptr;
+        cur_type = ptr_decl
+        pointer_type_name = ""
+
+        while isinstance(cur_type, c_ast.PtrDecl) or isinstance(
+            cur_type, c_ast.TypeDecl
+        ):
+            if isinstance(cur_type, c_ast.PtrDecl):
+                cur_type = cur_type.type
+                pointer_type_name += "*"
+            elif isinstance(cur_type, c_ast.TypeDecl):
+                if isinstance(cur_type.type, c_ast.IdentifierType):
+                    base_type_name = " ".join(cur_type.type.names)
+                    pointer_type_name = base_type_name + pointer_type_name
+                    return pointer_type_name
+                else:
+                    pointer_type_name = "".join(cur_type.type.name) + pointer_type_name
+                    return pointer_type_name
+        return None
+
+    resolved_type = typedefs.get(type_name)
+
+    if resolved_type is None:
+        return type_name
+
+    if isinstance(resolved_type, c_ast.TypeDecl):
+        if isinstance(resolved_type.type, c_ast.Enum):
+            print(f"Resolved enum typedef {type_name}")
+            return type_name 
+
+        if isinstance(resolved_type.type, c_ast.Struct):
+            print(f"Resolved struct typedef {type_name}")
+            return type_name
+
+        if isinstance(resolved_type.type, c_ast.Union):
+            print(f"Resolved union typedef {type_name}")
+            return type_name
+
+        if isinstance(resolved_type.type, c_ast.IdentifierType):
+            base_type_name = " ".join(resolved_type.type.names)
+            print(f"Resolved base typedef {type_name} to {base_type_name}")
+            return type_name 
+
+        resolved_type.show()
+        raise Exception(f"Unhandled TypeDecl typedef {type_name}")
+    elif isinstance(resolved_type, c_ast.PtrDecl):
+        pointer_type_name = resolve_base_type(resolved_type)
+        print(f"Resolved pointer typedef {type_name} to {pointer_type_name}")
+        return pointer_type_name
+    else:
+        resolved_type.show()
+        raise Exception(f"Unhandled typedef {type_name}")
+
+
+def generate_checked_function(func, typedefs):
     func_name = func.name  # Access the name directly from Decl
     new_func_name = f"{func_name}_checked"
 
@@ -17,8 +85,9 @@ def generate_checked_function(func):
     return_type = "void"  # Default to void if no return type is specified
     if isinstance(func.type.type, c_ast.TypeDecl):
         return_type = " ".join(func.type.type.type.names)
-        # TODO: figure out a better way to detect typedef from pointer
-        if isinstance(func.type.type, c_ast.PtrDecl):
+
+        resolved_type = resolve_typedef(typedefs, return_type)
+        if resolved_type.endswith("*"):
             return_pointer = True
 
     # Start building the new function
@@ -88,12 +157,13 @@ def generate_checked_function(func):
     else:
         new_func.append(f"    if (original_result == 0) {{")
         new_func.append(f"        res.error_code = 0;")
-        new_func.append(f"        res.value._Bool_value = original_result;")
+        new_func.append(f"        res.value.{return_type}_value = original_result;")
         new_func.append(f"    }} else {{")
         new_func.append(f"        res.error_code = -2;")
         new_func.append(f"    }}")
 
     new_func.append(f"    return res;")
+    new_func.append(f"}}")
     return "\n".join(new_func)
 
 
@@ -139,6 +209,9 @@ def process_header():
         ],
     )
 
+    # Collect all typedefs
+    typedefs = collect_typedefs(ast)
+
     # Collect all function declarations
     functions = [
         node
@@ -151,7 +224,8 @@ def process_header():
     for func in functions:
         if isinstance(func.type.type, c_ast.TypeDecl):
             return_type = " ".join(func.type.type.type.names)
-            return_types.add(return_type)
+            resolved_type = resolve_typedef(typedefs, return_type)
+            return_types.add(resolved_type)
 
     # Update the Result struct with all return types
     for return_type in return_types:
@@ -180,7 +254,7 @@ def process_header():
         f.write(RESULT_STRUCT + "\n")
 
         for func in functions:
-            new_func = generate_checked_function(func)
+            new_func = generate_checked_function(func, typedefs)
             f.write(new_func + "\n\n")
 
         f.write("#endif // WASM_EXPORT_CHECKED_H\n")