diff --git a/tools/release.py b/tools/release.py
index 0263d9a9e6f6ea9ca23cac69112e12a977b6b1df..689c1b26d8474c9356bcdfcf23d15b0c5eeb7728 100755
--- a/tools/release.py
+++ b/tools/release.py
@@ -207,7 +207,7 @@ def notary():
 
 
 def staple(bundle):
-    for attempt in range(2):
+    for attempt in range(5):
         with tempfile.TemporaryFile(mode='w+') as log:
             try:
                 try:
@@ -219,9 +219,10 @@ def staple(bundle):
                     print(diagnostic, end='', flush=True)
             except subprocess.CalledProcessError as error:
                 # EX_NOHOST alone also means the bundle has never been notarized.
-                if attempt or error.returncode != 68 or not re.search(
+                if attempt == 4 or error.returncode != 68 or not re.search(
                         r'^error is Error Domain=NSURLErrorDomain Code=-1005(?:\s|$)', diagnostic, re.M):
                     raise
+                time.sleep(10 * 2 ** attempt)
             else:
                 return
 
diff --git a/tools/test_release.py b/tools/test_release.py
index b3f6e5756bb0dd74b778eb2d432d02550a3edfd8..b49e1af7e5144c4e93668b52b93af025d6ace2b2 100644
--- a/tools/test_release.py
+++ b/tools/test_release.py
@@ -94,9 +94,9 @@ class ReleaseTest(unittest.TestCase):
         self.assertEqual(error.stderr, b'diagnostic')
         self.assertIn('codesign --verify Snowbound.app', printed.getvalue())
 
-    def test_staple_retries_only_a_lost_connection_and_propagates_second_failure(self):
+    def test_staple_retries_only_a_lost_connection_and_propagates_last_failure(self):
         network = 'error is Error Domain=NSURLErrorDomain Code=-1005 "The network connection was lost."\n'
-        for failures in ([(68, network)], [(68, network), (68, network)],
+        for failures in ([(68, network)], [(68, network)] * 4, [(68, network)] * 5,
                          [(68, 'The bundle has not been notarized.\n')],
                          [(77, network)], [(68, network.replace('-1005', '-10050'))]):
             with self.subTest(failures=failures), tempfile.TemporaryDirectory() as folder:
@@ -114,15 +114,18 @@ class ReleaseTest(unittest.TestCase):
                     kwargs['stdout'].write('The staple and validate action worked!\n')
 
                 printed = io.StringIO()
-                with patch.dict(release['staple'].__globals__, {'run': failing_tool}), redirect_stdout(printed):
-                    if len(failures) == 1 and failures[0] == (68, network):
+                sleep = Mock()
+                with patch.dict(release['staple'].__globals__, {'run': failing_tool}), \
+                        patch.object(release['time'], 'sleep', sleep), redirect_stdout(printed):
+                    if failures[0] == (68, network) and len(failures) < 5:
                         self.assertIsNone(release['staple'](Path(folder) / 'Snowbound.app'))
                     else:
                         with self.assertRaises(subprocess.CalledProcessError) as raised:
                             release['staple'](Path(folder) / 'Snowbound.app')
                         self.assertIs(raised.exception, errors[-1])
-                expected = 2 if failures[0] == (68, network) else 1
-                self.assertEqual(len(calls), expected)
+                retried = failures[0] == (68, network)
+                self.assertEqual(len(calls), min(len(failures) + 1, 5) if retried else 1)
+                self.assertEqual([wait for (wait,), _ in sleep.call_args_list], [10, 20, 40, 80][:len(calls) - 1])
                 self.assertEqual(printed.getvalue(), ''.join(text for _, text in failures) +
                                  ('The staple and validate action worked!\n' if len(errors) < len(calls) else ''))
                 for command, kwargs in calls: