diff --git a/send2trash/plat_osx.py b/send2trash/plat_osx.py
index ac6634c..ae3ffc3 100644
--- a/send2trash/plat_osx.py
+++ b/send2trash/plat_osx.py
@@ -4,53 +4,17 @@
 # which should be included with this package. The terms are also available at
 # http://www.hardcoded.net/licenses/bsd_license
 
-from __future__ import unicode_literals
+from platform import mac_ver
+from sys import version_info
 
-from ctypes import cdll, byref, Structure, c_char, c_char_p
-from ctypes.util import find_library
-
-from .compat import binary_type
-
-Foundation = cdll.LoadLibrary(find_library("Foundation"))
-CoreServices = cdll.LoadLibrary(find_library("CoreServices"))
-
-GetMacOSStatusCommentString = Foundation.GetMacOSStatusCommentString
-GetMacOSStatusCommentString.restype = c_char_p
-FSPathMakeRefWithOptions = CoreServices.FSPathMakeRefWithOptions
-FSMoveObjectToTrashSync = CoreServices.FSMoveObjectToTrashSync
-
-kFSPathMakeRefDefaultOptions = 0
-kFSPathMakeRefDoNotFollowLeafSymlink = 0x01
-
-kFSFileOperationDefaultOptions = 0
-kFSFileOperationOverwrite = 0x01
-kFSFileOperationSkipSourcePermissionErrors = 0x02
-kFSFileOperationDoNotMoveAcrossVolumes = 0x04
-kFSFileOperationSkipPreflight = 0x08
-
-
-class FSRef(Structure):
-    _fields_ = [("hidden", c_char * 80)]
-
-
-def check_op_result(op_result):
-    if op_result:
-        msg = GetMacOSStatusCommentString(op_result).decode("utf-8")
-        raise OSError(msg)
-
-
-def send2trash(paths):
-    if not isinstance(paths, list):
-        paths = [paths]
-    paths = [
-        path.encode("utf-8") if not isinstance(path, binary_type) else path
-        for path in paths
-    ]
-    for path in paths:
-        fp = FSRef()
-        opts = kFSPathMakeRefDoNotFollowLeafSymlink
-        op_result = FSPathMakeRefWithOptions(path, opts, byref(fp), None)
-        check_op_result(op_result)
-        opts = kFSFileOperationDefaultOptions
-        op_result = FSMoveObjectToTrashSync(byref(fp), None, opts)
-        check_op_result(op_result)
+# If macOS is 11.0 or newer try to use the pyobjc version to get around #51
+# NOTE: pyobjc only supports python >= 3.6
+if version_info >= (3, 6) and int(mac_ver()[0].split(".", 1)[0]) >= 11:
+    try:
+        from .plat_osx_pyobjc import send2trash
+    except ImportError:
+        # Try to fall back to ctypes version, although likely problematic still
+        from .plat_osx_ctypes import send2trash
+else:
+    # Just use the old version otherwise
+    from .plat_osx_ctypes import send2trash  # noqa: F401
diff --git a/send2trash/plat_osx_ctypes.py b/send2trash/plat_osx_ctypes.py
new file mode 100644
index 0000000..ac6634c
--- /dev/null
+++ b/send2trash/plat_osx_ctypes.py
@@ -0,0 +1,56 @@
+# Copyright 2017 Virgil Dupras
+
+# This software is licensed under the "BSD" License as described in the "LICENSE" file,
+# which should be included with this package. The terms are also available at
+# http://www.hardcoded.net/licenses/bsd_license
+
+from __future__ import unicode_literals
+
+from ctypes import cdll, byref, Structure, c_char, c_char_p
+from ctypes.util import find_library
+
+from .compat import binary_type
+
+Foundation = cdll.LoadLibrary(find_library("Foundation"))
+CoreServices = cdll.LoadLibrary(find_library("CoreServices"))
+
+GetMacOSStatusCommentString = Foundation.GetMacOSStatusCommentString
+GetMacOSStatusCommentString.restype = c_char_p
+FSPathMakeRefWithOptions = CoreServices.FSPathMakeRefWithOptions
+FSMoveObjectToTrashSync = CoreServices.FSMoveObjectToTrashSync
+
+kFSPathMakeRefDefaultOptions = 0
+kFSPathMakeRefDoNotFollowLeafSymlink = 0x01
+
+kFSFileOperationDefaultOptions = 0
+kFSFileOperationOverwrite = 0x01
+kFSFileOperationSkipSourcePermissionErrors = 0x02
+kFSFileOperationDoNotMoveAcrossVolumes = 0x04
+kFSFileOperationSkipPreflight = 0x08
+
+
+class FSRef(Structure):
+    _fields_ = [("hidden", c_char * 80)]
+
+
+def check_op_result(op_result):
+    if op_result:
+        msg = GetMacOSStatusCommentString(op_result).decode("utf-8")
+        raise OSError(msg)
+
+
+def send2trash(paths):
+    if not isinstance(paths, list):
+        paths = [paths]
+    paths = [
+        path.encode("utf-8") if not isinstance(path, binary_type) else path
+        for path in paths
+    ]
+    for path in paths:
+        fp = FSRef()
+        opts = kFSPathMakeRefDoNotFollowLeafSymlink
+        op_result = FSPathMakeRefWithOptions(path, opts, byref(fp), None)
+        check_op_result(op_result)
+        opts = kFSFileOperationDefaultOptions
+        op_result = FSMoveObjectToTrashSync(byref(fp), None, opts)
+        check_op_result(op_result)
diff --git a/send2trash/plat_osx_pyobjc.py b/send2trash/plat_osx_pyobjc.py
new file mode 100644
index 0000000..e34726e
--- /dev/null
+++ b/send2trash/plat_osx_pyobjc.py
@@ -0,0 +1,29 @@
+# Copyright 2017 Virgil Dupras
+
+# This software is licensed under the "BSD" License as described in the "LICENSE" file,
+# which should be included with this package. The terms are also available at
+# http://www.hardcoded.net/licenses/bsd_license
+
+from Foundation import NSFileManager, NSURL
+from .compat import text_type
+
+
+def check_op_result(op_result):
+    # First value will be false on failure
+    if not op_result[0]:
+        # Error is in third value, localized failure reason matchs ctypes version
+        raise OSError(op_result[2].localizedFailureReason())
+
+
+def send2trash(paths):
+    if not isinstance(paths, list):
+        paths = [paths]
+    paths = [
+        path.decode("utf-8") if not isinstance(path, text_type) else path
+        for path in paths
+    ]
+    for path in paths:
+        file_url = NSURL.fileURLWithPath_(path)
+        fm = NSFileManager.defaultManager()
+        op_result = fm.trashItemAtURL_resultingItemURL_error_(file_url, None, None)
+        check_op_result(op_result)
diff --git a/tox.ini b/tox.ini
index 416e921..6c69397 100644
--- a/tox.ini
+++ b/tox.ini
@@ -7,6 +7,7 @@ deps =
     flake8
     pytest
     pywin32; sys_platform == 'win32'
+    pyobjc-framework-Cocoa; sys_platform == 'darwin'
 commands =
     flake8
     pytest