diff --git a/beets/dbcore/pathutils.py b/beets/dbcore/pathutils.py
index 16071a3c8..49d76cf2f 100644
--- a/beets/dbcore/pathutils.py
+++ b/beets/dbcore/pathutils.py
@@ -8,6 +8,15 @@ from beets import context, util
 MaybeBytes = TypeVar("MaybeBytes", bytes, None)
 
 
+def _is_same_path_or_child(path: bytes, music_dir: bytes) -> bool:
+    """Check if path is the music directory itself or resides within it."""
+    path_cmp = os.path.normcase(os.fsdecode(path))
+    music_dir_cmp = os.path.normcase(os.fsdecode(music_dir))
+    return path_cmp == music_dir_cmp or path_cmp.startswith(
+        os.path.join(music_dir_cmp, "")
+    )
+
+
 def normalize_path_for_db(path: MaybeBytes) -> MaybeBytes:
     """Convert an absolute library path to its database representation."""
     if not path or not os.path.isabs(path):
@@ -17,10 +26,7 @@ def normalize_path_for_db(path: MaybeBytes) -> MaybeBytes:
     if not music_dir:
         return path
 
-    if path == music_dir:
-        return os.path.relpath(path, music_dir)
-
-    if path.startswith(os.path.join(music_dir, b"")):
+    if _is_same_path_or_child(path, music_dir):
         return os.path.relpath(path, music_dir)
 
     return path
diff --git a/beets/library/models.py b/beets/library/models.py
index 18a7f413c..0c0f88fc3 100644
--- a/beets/library/models.py
+++ b/beets/library/models.py
@@ -12,8 +12,9 @@ from typing import TYPE_CHECKING, ClassVar
 from mediafile import MediaFile, UnreadableFileError
 
 import beets
-from beets import context, dbcore, logging, plugins, util
+from beets import dbcore, logging, plugins, util
 from beets.dbcore import types
+from beets.dbcore.pathutils import normalize_path_for_db
 from beets.util import (
     MoveOperation,
     bytestring_path,
@@ -104,19 +105,15 @@ class LibModel(dbcore.Model["Library"]):
         if (
             cls._type(field).query is dbcore.query.PathQuery
             and query_cls is not dbcore.query.PathQuery
-            and (music_dir := context.get_music_dir())
         ):
             # Regex, exact, and string queries operate on the raw DB value, so
             # strip the library prefix to match the stored relative path.
             if isinstance(pattern, bytes):
-                prefix = os.path.join(music_dir, b"")
-                if pattern.startswith(prefix):
-                    pattern = os.path.relpath(pattern, music_dir)
+                pattern = normalize_path_for_db(pattern)
             else:
-                music_dir_str = os.fsdecode(music_dir)
-                prefix = music_dir_str + os.sep
-                if pattern.startswith(prefix):
-                    pattern = pattern.removeprefix(prefix)
+                pattern = os.fsdecode(
+                    normalize_path_for_db(util.bytestring_path(pattern))
+                )
         if field in cls.shared_db_fields:
             # This field exists in both tables, so SQLite will encounter
             # an OperationalError if we try to use it in a query.
diff --git a/test/library/test_migrations.py b/test/library/test_migrations.py
index 34710f67f..53c52fa74 100644
--- a/test/library/test_migrations.py
+++ b/test/library/test_migrations.py
@@ -161,7 +161,7 @@ class TestRelativePathMigration:
         helper.teardown_beets()
 
     def test_migrate(self, helper: TestHelper):
-        relative_path = "foo/bar/baz.mp3"
+        relative_path = os.path.join("foo", "bar", "baz.mp3")
         absolute_path = os.fsencode(helper.lib_path / relative_path)
 
         # need to insert the path directly into the database to bypass the path setter
diff --git a/test/plugins/test_ipfs.py b/test/plugins/test_ipfs.py
index 5481b8585..00d6f0512 100644
--- a/test/plugins/test_ipfs.py
+++ b/test/plugins/test_ipfs.py
@@ -15,9 +15,9 @@
 import os
 from unittest.mock import Mock, patch
 
+from beets import util
 from beets.test import _common
 from beets.test.helper import PluginTestCase
-from beets.util import bytestring_path
 from beetsplug.ipfs import IPFSPlugin
 
 
@@ -37,10 +37,9 @@ class IPFSPluginTest(PluginTestCase):
             try:
                 if check_item.get("ipfs", with_album=False):
                     ipfs_item = os.fsdecode(os.path.basename(want_item.path))
-                    want_path = os.path.normpath(
-                        f"/ipfs/{test_album.ipfs}/{ipfs_item}"
+                    want_path = util.normpath(
+                        os.path.join("/ipfs", test_album.ipfs, ipfs_item)
                     )
-                    want_path = bytestring_path(want_path)
                     assert check_item.path == want_path
                     assert (
                         check_item.get("ipfs", with_album=False)
diff --git a/test/test_library.py b/test/test_library.py
index 274d2dea6..3f08feaeb 100644
--- a/test/test_library.py
+++ b/test/test_library.py
@@ -1094,7 +1094,7 @@ class PathStringTest(BeetsTestCase):
         assert isinstance(dest, bytes)
 
     def test_artpath_stores_special_chars(self):
-        path = b"b\xe1r"
+        path = bytestring_path("b\xe1r")
         alb = self.lib.add_album([self.i])
         alb.artpath = path
         alb.store()
@@ -1131,7 +1131,7 @@ class PathStringTest(BeetsTestCase):
         assert isinstance(alb.artpath, bytes)
 
     def test_relative_path_is_stored(self):
-        relative_path = b"abc/foo.mp3"
+        relative_path = os.path.join(b"abc", b"foo.mp3")
         absolute_path = os.path.join(self.libdir, relative_path)
         self.i.path = absolute_path
         self.i.store()