diff --git a/beets/library.py b/beets/library.py
index 10cddc69d..18b739902 100644
--- a/beets/library.py
+++ b/beets/library.py
@@ -24,7 +24,6 @@ import unicodedata
 import time
 import re
 from unidecode import unidecode
-import platform
 
 from beets import logging
 from beets.mediafile import MediaFile, MutagenError, UnreadableFileError
@@ -61,9 +60,11 @@ class PathQuery(dbcore.FieldQuery):
         """
         super(PathQuery, self).__init__(field, pattern, fast)
 
-        # By default, the case sensitivity depends on the platform.
+        # By default, the case sensitivity depends on the filesystem
+        # the library is located on.
         if case_sensitive is None:
-            case_sensitive = platform.system() != 'Windows'
+            case_sensitive = beets.util.is_filesystem_case_sensitive(
+                beets.config['directory'].get())
         self.case_sensitive = case_sensitive
 
         # Use a normalized-case pattern for case-insensitive matches.
diff --git a/beets/util/__init__.py b/beets/util/__init__.py
index 158a6c8e1..1f9279b25 100644
--- a/beets/util/__init__.py
+++ b/beets/util/__init__.py
@@ -16,6 +16,7 @@
 
 from __future__ import (division, absolute_import, print_function,
                         unicode_literals)
+import ctypes
 
 import os
 import sys
@@ -760,3 +761,52 @@ def interactive_open(targets, command=None):
     command += targets
 
     return os.execlp(*command)
+
+
+def is_filesystem_case_sensitive(path):
+    """Checks if the filesystem at the given path is case sensitive.
+    If the path does not exist, a case sensitive file system is
+    assumed if the system is not windows.
+
+    :param path: The path to check for case sensitivity.
+    :return: True if the file system is case sensitive, False else.
+    """
+    if os.path.exists(path):
+        # Check if the path to the library exists in lower and upper case
+        if os.path.exists(path.lower()) and \
+           os.path.exists(path.upper()):
+            # All the paths may exist on the file system. Check if they
+            # refer to different files
+            if platform.system() != 'Windows':
+                # os.path.samefile is only available on Unix systems for
+                # python < 3.0
+                return not os.path.samefile(path.lower(),
+                                            path.upper())
+
+            # On windows we use GetLongPathNameW to determine the real path
+            # using the actual case.
+            def get_long_path_name(short_path):
+                if not isinstance(short_path, unicode):
+                    short_path = unicode(short_path)
+                buf = ctypes.create_unicode_buffer(260)
+                get_long_path_name_w = ctypes.windll.kernel32.GetLongPathNameW
+                return_value = get_long_path_name_w(short_path, buf, 260)
+                if return_value == 0 or return_value > 260:
+                    # An error occurred
+                    return short_path
+                else:
+                    long_path = buf.value
+                    # GetLongPathNameW does not change the case of the drive
+                    # letter.
+                    if len(long_path) > 1 and long_path[1] == ':':
+                        long_path = long_path[0].upper() + long_path[1:]
+                    return long_path
+
+            lower = get_long_path_name(path.lower())
+            upper = get_long_path_name(path.upper())
+
+            return lower != upper
+        else:
+            return True
+    # By default, the case sensitivity depends on the platform.
+    return platform.system() != 'Windows'
diff --git a/docs/changelog.rst b/docs/changelog.rst
index 1aa89ef1e..825a8a36e 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -46,6 +46,8 @@ Fixes:
   written to files. Thanks to :user:`jdetrey`. :bug:`1303` :bug:`1589`
 * :doc:`/plugins/replaygain`: Avoid a crash when the PyAudioTools backend
   encounters an error. :bug:`1592`
+* The check whether the file system is case sensitive or not could lead to
+  wrong results. It is much more robust now.
 * Case-insensitive path queries might have returned nothing because of a
   wrong SQL query.
 * Fix a crash when a query contains a "+" or "-" alone in a component.
diff --git a/docs/reference/query.rst b/docs/reference/query.rst
index e2091bb14..e3ce68004 100644
--- a/docs/reference/query.rst
+++ b/docs/reference/query.rst
@@ -202,8 +202,8 @@ Note that this only matches items that are *already in your library*, so a path
 query won't necessarily find *all* the audio files in a directory---just the
 ones you've already added to your beets library.
 
-Path queries are case-sensitive on most platforms but case-insensitive on
-Windows.
+Path queries are case-sensitive if the file system the library is located on
+is case-sensitive, case-insensitive otherwise.
 
 .. _query-sort:
 
diff --git a/test/test_query.py b/test/test_query.py
index 04235906d..4dcf52a21 100644
--- a/test/test_query.py
+++ b/test/test_query.py
@@ -376,12 +376,17 @@ class PathQueryTest(_common.LibTestCase, TestHelper, AssertsMixin):
         self.i.store()
         self.lib.add_album([self.i])
 
-        self.patcher = patch('beets.library.os.path.exists')
-        self.patcher.start().return_value = True
+        self.patcher_exists = patch('beets.library.os.path.exists')
+        self.patcher_exists.start().return_value = True
+
+        self.patcher_samefile = patch('beets.library.os.path.samefile')
+        self.patcher_samefile.start().return_value = True
 
     def tearDown(self):
         super(PathQueryTest, self).tearDown()
-        self.patcher.stop()
+
+        self.patcher_samefile.stop()
+        self.patcher_exists.stop()
 
     def test_path_exact_match(self):
         q = 'path:/a/b/c.mp3'
@@ -503,7 +508,27 @@ class PathQueryTest(_common.LibTestCase, TestHelper, AssertsMixin):
         results = self.lib.items(makeq(case_sensitive=False))
         self.assert_items_matched(results, ['path item', 'caps path'])
 
-        # test platform-aware default sensitivity
+        # Check for correct case sensitivity selection (this check
+        # only works for non-windows os)
+        with _common.system_mock('Darwin'):
+            # exists = True and samefile = True => Case insensitive
+            q = makeq()
+            self.assertEqual(q.case_sensitive, False)
+
+            self.patcher_samefile.stop()
+            self.patcher_samefile.start().return_value = False
+
+            # exists = True and samefile = False => Case sensitive
+            q = makeq()
+            self.assertEqual(q.case_sensitive, True)
+
+            self.patcher_samefile.stop()
+            self.patcher_samefile.start().return_value = True
+
+        # test platform-aware default sensitivity when the library
+        # path does not exist (exist = False)
+        self.patcher_exists.stop()
+        self.patcher_exists.start().return_value = False
         with _common.system_mock('Darwin'):
             q = makeq()
             self.assertEqual(q.case_sensitive, True)
@@ -511,6 +536,8 @@ class PathQueryTest(_common.LibTestCase, TestHelper, AssertsMixin):
         with _common.system_mock('Windows'):
             q = makeq()
             self.assertEqual(q.case_sensitive, False)
+        self.patcher_exists.stop()
+        self.patcher_exists.start().return_value = True
 
     @patch('beets.library.os')
     def test_path_sep_detection(self, mock_os):
@@ -526,7 +553,7 @@ class PathQueryTest(_common.LibTestCase, TestHelper, AssertsMixin):
 
     def test_path_detection(self):
         # cover existence test
-        self.patcher.stop()
+        self.patcher_exists.stop()
         is_path = beets.library.PathQuery.is_path_query
 
         try:
@@ -546,7 +573,7 @@ class PathQueryTest(_common.LibTestCase, TestHelper, AssertsMixin):
             finally:
                 os.chdir(cur_dir)
         finally:
-            self.patcher.start()
+            self.patcher_exists.start()
 
 
 class IntQueryTest(unittest.TestCase, TestHelper):