diff --git a/jedi/evaluate/compiled/context.py b/jedi/evaluate/compiled/context.py
index 52bba972..36f1936b 100644
--- a/jedi/evaluate/compiled/context.py
+++ b/jedi/evaluate/compiled/context.py
@@ -5,7 +5,7 @@ import re
 from functools import partial
 
 from jedi import debug
-from jedi._compatibility import force_unicode, Parameter
+from jedi._compatibility import force_unicode, Parameter, cast_path
 from jedi.cache import underscore_memoization, memoize_method
 from jedi.evaluate.filters import AbstractFilter
 from jedi.evaluate.names import AbstractNameDefinition, ContextNameMixin
@@ -80,7 +80,7 @@ class CompiledObject(Context):
 
     @CheckAttribute()
     def py__path__(self):
-        return self.access_handle.py__path__()
+        return map(cast_path, self.access_handle.py__path__())
 
     @property
     def string_names(self):
@@ -97,7 +97,7 @@ class CompiledObject(Context):
         return self.access_handle.py__bool__()
 
     def py__file__(self):
-        return self.access_handle.py__file__()
+        return cast_path(self.access_handle.py__file__())
 
     def is_class(self):
         return self.access_handle.is_class()
diff --git a/jedi/evaluate/gradual/typeshed.py b/jedi/evaluate/gradual/typeshed.py
index 377d270b..f069c0c8 100644
--- a/jedi/evaluate/gradual/typeshed.py
+++ b/jedi/evaluate/gradual/typeshed.py
@@ -2,7 +2,7 @@ import os
 import re
 
 from parso.file_io import FileIO
-from jedi._compatibility import FileNotFoundError
+from jedi._compatibility import FileNotFoundError, cast_path
 from jedi.parser_utils import get_cached_code_lines
 from jedi.evaluate.cache import evaluator_function_cache
 from jedi.evaluate.base_context import ContextSet
@@ -31,6 +31,7 @@ def _create_stub_map(directory):
             return
 
         for entry in listed:
+            entry = cast_path(entry)
             path = os.path.join(directory, entry)
             if os.path.isdir(path):
                 init = os.path.join(path, '__init__.pyi')