diff --git a/src/outline_tool.py b/src/outline_tool.py
index 49cef487..41d94236 100644
--- a/src/outline_tool.py
+++ b/src/outline_tool.py
@@ -34,12 +34,14 @@ import ast
 
 from pathlib import Path
 
+from src.result_types import Result, ErrorInfo, ErrorKind
+
 
 class CodeOutliner:
  def __init__(self) -> None:
   pass
 
- def outline(self, code: str) -> str:
+ def outline(self, code: str) -> Result[str]:
   """
   [C: tests/test_outline_tool.py:test_code_outliner_imgui_scopes, tests/test_outline_tool.py:test_code_outliner_nested_ifs, tests/test_outline_tool.py:test_code_outliner_type_hints]
   """
@@ -47,8 +49,9 @@ class CodeOutliner:
   try:
    tree = ast.parse(code)
   except SyntaxError as e:
-   return f"ERROR parsing code: {e}"
-  output = []
+   return Result(data=f"ERROR parsing code: {e}", errors=[ErrorInfo(kind=ErrorKind.INVALID_INPUT, message=str(e), source="outline_tool.outline", original=e)])
+  output: list[str] = []
+  parse_errors: list[ErrorInfo] = []
 
   def get_docstring(node: ast.AST) -> str | None:
    if isinstance(node, (ast.AsyncFunctionDef, ast.FunctionDef, ast.ClassDef, ast.Module)):
@@ -87,8 +90,8 @@ class CodeOutliner:
     if getattr(node, "returns", None):
      try:
       returns = f" -> {ast.unparse(node.returns)}"
-     except (ValueError, TypeError):
-      pass
+     except (ValueError, TypeError) as e:
+      parse_errors.append(ErrorInfo(kind=ErrorKind.INTERNAL, message=f"ast.unparse failed for {node.name}.returns: {e}", source="outline_tool.walk", original=e))
     output.append(f"{'  ' * indent}{prefix} {node.name}{returns} (Lines {start_line}-{end_line})")
     doc = get_docstring(node)
     if doc:
@@ -106,8 +109,8 @@ class CodeOutliner:
        output.append(f"{'  ' * indent}[ImGui Scope] {ctx_str} (Lines {start_line}-{end_line})")
        is_imgui = True
        break
-    except (ValueError, TypeError, AttributeError):
-     pass
+    except (ValueError, TypeError, AttributeError) as e:
+     parse_errors.append(ErrorInfo(kind=ErrorKind.INTERNAL, message=f"ast.unparse failed for ImGui context: {e}", source="outline_tool.walk", original=e))
     for item in node.body:
      walk(item, indent + 1 if is_imgui else indent)
    else:
@@ -119,12 +122,12 @@ class CodeOutliner:
   
   for node in tree.body:
    walk(node)
-  return "\n".join(output)
+  return Result(data="\n".join(output), errors=parse_errors)
 
-def get_outline(path: Path, code: str) -> str:
+def get_outline(path: Path, code: str) -> Result[str]:
  suffix = path.suffix.lower()
  if suffix == ".py":
   outliner = CodeOutliner()
   return outliner.outline(code)
  else:
-  return f"Outlining not supported for {suffix} files yet."
\ No newline at end of file
+  return Result(data=f"Outlining not supported for {suffix} files yet.")
\ No newline at end of file
diff --git a/tests/test_outline_tool.py b/tests/test_outline_tool.py
index 034ff0be..5bc8a7ff 100644
--- a/tests/test_outline_tool.py
+++ b/tests/test_outline_tool.py
@@ -8,14 +8,15 @@ def test_code_outliner_type_hints():
 class Test:
     def my_method(self, x: int) -> str:
         return "hello"
-        
+
 def my_func(a: bool) -> None:
     pass
 """
     outliner = CodeOutliner()
     result = outliner.outline(code)
-    assert "[Method] my_method -> str (Lines 3-4)" in result
-    assert "[Func] my_func -> None (Lines 6-7)" in result
+    assert result.ok, f"outline failed: {result.errors}"
+    assert "[Method] my_method -> str (Lines 3-4)" in result.data
+    assert "[Func] my_func -> None (Lines 6-7)" in result.data
 
 def test_code_outliner_imgui_scopes():
     code = """
@@ -27,8 +28,9 @@ def render_gui() -> None:
 """
     outliner = CodeOutliner()
     result = outliner.outline(code)
-    assert "[ImGui Scope] imscope.window('My Window') (Lines 3-6)" in result
-    assert "[ImGui Scope] imscope.child('My Child') (Lines 5-6)" in result
+    assert result.ok, f"outline failed: {result.errors}"
+    assert "[ImGui Scope] imscope.window('My Window') (Lines 3-6)" in result.data
+    assert "[ImGui Scope] imscope.child('My Child') (Lines 5-6)" in result.data
 
 def test_code_outliner_nested_ifs():
     code = """
@@ -39,4 +41,5 @@ def render_gui() -> None:
 """
     outliner = CodeOutliner()
     result = outliner.outline(code)
-    assert "[ImGui Scope] imscope.window('My Window') (Lines 4-5)" in result
+    assert result.ok, f"outline failed: {result.errors}"
+    assert "[ImGui Scope] imscope.window('My Window') (Lines 4-5)" in result.data