diff --git a/jedi/inference/sys_path.py b/jedi/inference/sys_path.py
index 23068e4b..38d96221 100644
--- a/jedi/inference/sys_path.py
+++ b/jedi/inference/sys_path.py
@@ -1,6 +1,6 @@
 import os
 import re
-from pathlib import Path, PurePath
+from pathlib import Path
 from importlib.machinery import all_suffixes
 
 from jedi.inference.cache import inference_state_method_cache
@@ -15,7 +15,7 @@ _BUILDOUT_PATH_INSERTION_LIMIT = 10
 
 
 def _abs_path(module_context, path: str):
-    path = PurePath(path)
+    path = Path(path)
     if path.is_absolute():
         return path
 
@@ -219,7 +219,7 @@ def transform_path_to_dotted(sys_path, module_path):
     """
     Returns the dotted path inside a sys.path as a list of names. e.g.
 
-    >>> transform_path_to_dotted(["/foo"], Path('/foo/bar/baz.py'))
+    >>> transform_path_to_dotted([str(Path("/foo").absolute())], Path('/foo/bar/baz.py').absolute())
     (('bar', 'baz'), False)
 
     Returns (None, False) if the path doesn't really resolve to anything.
diff --git a/test/test_inference/test_buildout_detection.py b/test/test_inference/test_buildout_detection.py
index f15e9a78..4817339d 100644
--- a/test/test_inference/test_buildout_detection.py
+++ b/test/test_inference/test_buildout_detection.py
@@ -58,17 +58,17 @@ def test_sys_path_with_modifications(Script):
     """)
 
     paths = Script(code, path=path)._inference_state.get_sys_path()
-    assert '/tmp/.buildout/eggs/important_package.egg' in paths
+    assert os.path.abspath('/tmp/.buildout/eggs/important_package.egg') in paths
 
 
 def test_path_from_sys_path_assignment(Script):
-    code = dedent("""
+    code = dedent(f"""
         #!/usr/bin/python
 
         import sys
         sys.path[0:0] = [
-          '/usr/lib/python3.8/site-packages',
-          '/home/test/.buildout/eggs/important_package.egg'
+          {os.path.abspath('/usr/lib/python3.8/site-packages')!r},
+          {os.path.abspath('/home/test/.buildout/eggs/important_package.egg')!r},
           ]
 
         path[0:0] = [1]
diff --git a/test/test_inference/test_sys_path.py b/test/test_inference/test_sys_path.py
index e0c6d74e..2fa0e4df 100644
--- a/test/test_inference/test_sys_path.py
+++ b/test/test_inference/test_sys_path.py
@@ -2,7 +2,7 @@ import os
 from glob import glob
 import sys
 import shutil
-from pathlib import Path, PurePath
+from pathlib import Path
 
 import pytest
 
@@ -18,9 +18,9 @@ def test_paths_from_assignment(Script):
         return set(sys_path._paths_from_assignment(script._get_module_context(), expr_stmt))
 
     # Normalize paths for Windows.
-    path_a = PurePath('/foo/a')
-    path_b = PurePath('/foo/b')
-    path_c = PurePath('/foo/c')
+    path_a = Path('/foo/a').absolute()
+    path_b = Path('/foo/b').absolute()
+    path_c = Path('/foo/c').absolute()
 
     assert paths('sys.path[0:0] = ["a"]') == {path_a}
     assert paths('sys.path = ["b", 1, x + 3, y, "c"]') == {path_b, path_c}