diff --git a/changelog/11895.bugfix.rst b/changelog/11895.bugfix.rst
new file mode 100644
index 00000000000..4211213c1e5
--- /dev/null
+++ b/changelog/11895.bugfix.rst
@@ -0,0 +1 @@
+Fix collection on Windows where initial paths contain the short version of a path (for example ``c:\PROGRA~1\tests``).
diff --git a/src/_pytest/main.py b/src/_pytest/main.py
index f1c05754b2f..fd9dddfa318 100644
--- a/src/_pytest/main.py
+++ b/src/_pytest/main.py
@@ -902,6 +902,10 @@ def collect(self) -> Iterator[Union[nodes.Item, nodes.Collector]]:
                     # Path part e.g. `/a/b/` in `/a/b/test_file.py::TestIt::test_it`.
                     if isinstance(matchparts[0], Path):
                         is_match = node.path == matchparts[0]
+                        if sys.platform == "win32" and not is_match:
+                            # In case the file paths do not match, fallback to samefile() to
+                            # account for short-paths on Windows (#11895).
+                            is_match = os.path.samefile(node.path, matchparts[0])
                     # Name part e.g. `TestIt` in `/a/b/test_file.py::TestIt::test_it`.
                     else:
                         # TODO: Remove parametrized workaround once collection structure contains
diff --git a/testing/test_collection.py b/testing/test_collection.py
index b2780eb73ae..c7923c5efb6 100644
--- a/testing/test_collection.py
+++ b/testing/test_collection.py
@@ -3,9 +3,11 @@
 import pprint
 import shutil
 import sys
+import tempfile
 import textwrap
 from typing import List
 
+from _pytest.assertion.util import running_on_ci
 from _pytest.config import ExitCode
 from _pytest.fixtures import FixtureRequest
 from _pytest.main import _in_venv
@@ -1758,3 +1760,29 @@ def test_foo(): assert True
 
     assert result.ret == ExitCode.OK
     assert result.parseoutcomes() == {"passed": 1}
+
+
+@pytest.mark.skipif(not sys.platform.startswith("win"), reason="Windows only")
+def test_collect_short_file_windows(pytester: Pytester) -> None:
+    """Reproducer for #11895: short paths not colleced on Windows."""
+    short_path = tempfile.mkdtemp()
+    if "~" not in short_path:  # pragma: no cover
+        if running_on_ci():
+            # On CI, we are expecting that under the current GitHub actions configuration,
+            # tempfile.mkdtemp() is producing short paths, so we want to fail to prevent
+            # this from silently changing without us noticing.
+            pytest.fail(
+                f"tempfile.mkdtemp() failed to produce a short path on CI: {short_path}"
+            )
+        else:
+            # We want to skip failing this test locally in this situation because
+            # depending on the local configuration tempfile.mkdtemp() might not produce a short path:
+            # For example, user might have configured %TEMP% exactly to avoid generating short paths.
+            pytest.skip(
+                f"tempfile.mkdtemp() failed to produce a short path: {short_path}, skipping"
+            )
+
+    test_file = Path(short_path).joinpath("test_collect_short_file_windows.py")
+    test_file.write_text("def test(): pass", encoding="UTF-8")
+    result = pytester.runpytest(short_path)
+    assert result.parseoutcomes() == {"passed": 1}