diff --git a/Lib/shutil.py b/Lib/shutil.py
index a4aa0dfdd10b09..fcb3975ba33445 100644
--- a/Lib/shutil.py
+++ b/Lib/shutil.py
@@ -5,6 +5,7 @@
 """
 
 import os
+import platform
 import sys
 import stat
 import fnmatch
@@ -311,6 +312,31 @@ def _copyxattr(src, dst, *, follow_symlinks=True):
     def _copyxattr(*args, **kwargs):
         pass
 
+if sys.platform == 'darwin':
+    # As of macOS 10.10, the `copyfile` API changed to not copy certain flags.
+    # This corresponds to kernel version 14.0.
+    mac_ver = tuple(int(x) for x in os.uname().release.split('.'))
+    if mac_ver >= (14, 0, 0):
+        def _fix_flags(dst, flags, follow_symlinks):
+            """Perform any modifications to `flags` before they can be applied
+            to `dst` with `chflags()`.
+
+            """
+            # Based on copyfile's copyfile_stat()
+            omit_flags = (stat.UF_TRACKED | stat.SF_RESTRICTED)
+            add_flags  = 0
+
+            # If the kernel automatically put SF_RESTRICTED on the destination
+            # already, we don't want to clear it
+            st = os.stat(dst, follow_symlinks=follow_symlinks)
+            add_flags |= (st.st_flags & stat.SF_RESTRICTED)
+
+            return (flags & ~omit_flags) | add_flags
+
+if '_fix_flags' not in vars():
+    def _fix_flags(dst, flags, *args, **kwargs):
+        return flags
+
 def copystat(src, dst, *, follow_symlinks=True):
     """Copy all stat info (mode bits, atime, mtime, flags) from src to dst.
 
@@ -356,7 +382,8 @@ def lookup(name):
         pass
     if hasattr(st, 'st_flags'):
         try:
-            lookup("chflags")(dst, st.st_flags, follow_symlinks=follow)
+            flags = _fix_flags(dst, st.st_flags, follow_symlinks=follow)
+            lookup("chflags")(dst, flags, follow_symlinks=follow)
         except OSError as why:
             for err in 'EOPNOTSUPP', 'ENOTSUP':
                 if hasattr(errno, err) and why.errno == getattr(errno, err):
diff --git a/Lib/stat.py b/Lib/stat.py
index 46837c06dacfb8..61066eb9e8c691 100644
--- a/Lib/stat.py
+++ b/Lib/stat.py
@@ -100,11 +100,13 @@ def S_ISSOCK(mode):
 UF_APPEND    = 0x00000004  # file may only be appended to
 UF_OPAQUE    = 0x00000008  # directory is opaque when viewed through a union stack
 UF_NOUNLINK  = 0x00000010  # file may not be renamed or deleted
-UF_COMPRESSED = 0x00000020 # OS X: file is hfs-compressed
-UF_HIDDEN    = 0x00008000  # OS X: file should not be displayed
+UF_COMPRESSED = 0x00000020 # macOS: file is compressed (some file-systems)
+UF_TRACKED   = 0x00000040  # macOS: file renames and deletes are tracked
+UF_HIDDEN    = 0x00008000  # macOS: file should not be displayed
 SF_ARCHIVED  = 0x00010000  # file may be archived
 SF_IMMUTABLE = 0x00020000  # file may not be changed
 SF_APPEND    = 0x00040000  # file may only be appended to
+SF_RESTRICTED = 0x00080000 # macOS: entitlement required for writing
 SF_NOUNLINK  = 0x00100000  # file may not be renamed or deleted
 SF_SNAPSHOT  = 0x00200000  # file is a snapshot file
 
diff --git a/Lib/test/test_shutil.py b/Lib/test/test_shutil.py
index 7e0a3292e0f8a4..6759583ad239fd 100644
--- a/Lib/test/test_shutil.py
+++ b/Lib/test/test_shutil.py
@@ -33,7 +33,11 @@
 from test.support import TESTFN, FakePath
 
 TESTFN2 = TESTFN + "2"
+
 MACOS = sys.platform.startswith("darwin")
+if MACOS:
+    MACOS_VERS = tuple(int(x) for x in os.uname().release.split('.'))
+
 try:
     import grp
     import pwd
@@ -472,6 +476,19 @@ def _chflags_raiser(path, flags, *, follow_symlinks=True):
         finally:
             os.chflags = old_chflags
 
+    @unittest.skipUnless(MACOS and MACOS_VERS >= (14, 0, 0),
+                         "requires macOS 10.10 or newer")
+    def test_copystat_macos_restricted(self):
+        # A sample restricted file. This file has always been present on macOS.
+        src = '/System/Library/CoreServices/SystemVersion.plist'
+        dst = os.path.join(self.mkdtemp(), 'file1')
+        write_file(dst, 'foo')
+
+        # Check that the file is restricted befre, but not after copying
+        self.assertNotEqual(os.stat(src).st_flags & stat.SF_RESTRICTED, 0)
+        shutil.copystat(src, dst)
+        self.assertEqual(os.stat(dst).st_flags & stat.SF_RESTRICTED, 0)
+
     @support.skip_unless_xattr
     def test_copyxattr(self):
         tmp_dir = self.mkdtemp()
diff --git a/Misc/NEWS.d/next/Library/2017-12-18-02-19-43.bpo-32347.f8FJmS.rst b/Misc/NEWS.d/next/Library/2017-12-18-02-19-43.bpo-32347.f8FJmS.rst
new file mode 100644
index 00000000000000..88e70ab85ff9c8
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2017-12-18-02-19-43.bpo-32347.f8FJmS.rst
@@ -0,0 +1,2 @@
+``shutil.copystat`` now implements flag copy behavior from ``copyfile(3)``
+on macOS 10.10 and above. Patch by Ryan Govostes.
\ No newline at end of file