diff --git a/packaging/whl.py b/packaging/whl.py
index 35856a759c..f30575ae1b 100644
--- a/packaging/whl.py
+++ b/packaging/whl.py
@@ -18,9 +18,25 @@
 import os
 import pkg_resources
 import re
+import stat
 import zipfile
 
 
+def current_umask():
+    """Get the current umask which involves having to set it temporarily."""
+    mask = os.umask(0)
+    os.umask(mask)
+    return mask
+
+
+def set_extracted_file_to_default_mode_plus_executable(path):
+    """
+    Make file present at path have execute for user/group/world
+    (chmod +x) is no-op on windows per python docs
+    """
+    os.chmod(path, (0o777 & ~current_umask() | 0o111))
+
+
 class Wheel(object):
 
   def __init__(self, path):
@@ -107,8 +123,21 @@ def extras(self):
     return self.metadata().get('extras', [])
 
   def expand(self, directory):
-    with zipfile.ZipFile(self.path(), 'r') as whl:
-      whl.extractall(directory)
+    with zipfile.ZipFile(self.path(), "r", allowZip64=True) as whl:
+        whl.extractall(directory)
+        # The following logic is borrowed from Pip:
+        # https://github.com/pypa/pip/blob/cc48c07b64f338ac5e347d90f6cb4efc22ed0d0b/src/pip/_internal/utils/unpacking.py#L240
+        for info in whl.infolist():
+            name = info.filename
+            # Do not attempt to modify directories.
+            if name.endswith("/") or name.endswith("\\"):
+                continue
+            mode = info.external_attr >> 16
+            # if mode and regular file and any execute permissions for
+            # user/group/world?
+            if mode and stat.S_ISREG(mode) and mode & 0o111:
+                name = os.path.join(directory, name)
+                set_extracted_file_to_default_mode_plus_executable(name)
 
   # _parse_metadata parses METADATA files according to https://www.python.org/dev/peps/pep-0314/
   def _parse_metadata(self, content):