diff --git a/Lib/test/test_urlparse.py b/Lib/test/test_urlparse.py
index 80fb9e5cd2a445..dcdbb1cc64fd28 100644
--- a/Lib/test/test_urlparse.py
+++ b/Lib/test/test_urlparse.py
@@ -72,20 +72,20 @@ class UrlParseTestCase(unittest.TestCase):
 
     def checkRoundtrips(self, url, parsed, split):
         result = urllib.parse.urlparse(url)
-        self.assertEqual(result, parsed)
+        self.assertSequenceEqual(result, parsed)
         t = (result.scheme, result.netloc, result.path,
              result.params, result.query, result.fragment)
-        self.assertEqual(t, parsed)
+        self.assertSequenceEqual(t, parsed)
         # put it back together and it should be the same
         result2 = urllib.parse.urlunparse(result)
-        self.assertEqual(result2, url)
-        self.assertEqual(result2, result.geturl())
+        self.assertSequenceEqual(result2, url)
+        self.assertSequenceEqual(result2, result.geturl())
 
         # the result of geturl() is a fixpoint; we can always parse it
         # again to get the same result:
         result3 = urllib.parse.urlparse(result.geturl())
         self.assertEqual(result3.geturl(), result.geturl())
-        self.assertEqual(result3,          result)
+        self.assertSequenceEqual(result3, result)
         self.assertEqual(result3.scheme,   result.scheme)
         self.assertEqual(result3.netloc,   result.netloc)
         self.assertEqual(result3.path,     result.path)
@@ -99,18 +99,18 @@ def checkRoundtrips(self, url, parsed, split):
 
         # check the roundtrip using urlsplit() as well
         result = urllib.parse.urlsplit(url)
-        self.assertEqual(result, split)
+        self.assertSequenceEqual(result, split)
         t = (result.scheme, result.netloc, result.path,
              result.query, result.fragment)
-        self.assertEqual(t, split)
+        self.assertSequenceEqual(t, split)
         result2 = urllib.parse.urlunsplit(result)
-        self.assertEqual(result2, url)
-        self.assertEqual(result2, result.geturl())
+        self.assertSequenceEqual(result2, url)
+        self.assertSequenceEqual(result2, result.geturl())
 
         # check the fixpoint property of re-parsing the result of geturl()
         result3 = urllib.parse.urlsplit(result.geturl())
         self.assertEqual(result3.geturl(), result.geturl())
-        self.assertEqual(result3,          result)
+        self.assertSequenceEqual(result3, result)
         self.assertEqual(result3.scheme,   result.scheme)
         self.assertEqual(result3.netloc,   result.netloc)
         self.assertEqual(result3.path,     result.path)
@@ -162,10 +162,15 @@ def test_roundtrips(self):
              ('svn+ssh', 'svn.zope.org', '/repos/main/ZConfig/trunk/',
               '', '')),
             ('git+ssh://git@github.com/user/project.git',
-            ('git+ssh', 'git@github.com','/user/project.git',
-             '','',''),
-            ('git+ssh', 'git@github.com','/user/project.git',
-             '', '')),
+             ('git+ssh', 'git@github.com','/user/project.git',
+              '','',''),
+             ('git+ssh', 'git@github.com','/user/project.git',
+              '', '')),
+            ('itms-services://?action=download-manifest&url=https://example.com/app',
+             ('itms-services', '', '', '',
+              'action=download-manifest&url=https://example.com/app', ''),
+             ('itms-services', '', '',
+              'action=download-manifest&url=https://example.com/app', '')),
             ]
         def _encode(t):
             return (t[0].encode('ascii'),
diff --git a/Lib/urllib/parse.py b/Lib/urllib/parse.py
index 5f95c5ff7f9c1c..777b7c53efe565 100644
--- a/Lib/urllib/parse.py
+++ b/Lib/urllib/parse.py
@@ -54,7 +54,7 @@
                'imap', 'wais', 'file', 'mms', 'https', 'shttp',
                'snews', 'prospero', 'rtsp', 'rtspu', 'rsync',
                'svn', 'svn+ssh', 'sftp', 'nfs', 'git', 'git+ssh',
-               'ws', 'wss']
+               'ws', 'wss', 'itms-services']
 
 uses_params = ['', 'ftp', 'hdl', 'prospero', 'http', 'imap',
                'https', 'shttp', 'rtsp', 'rtspu', 'sip', 'sips',
diff --git a/Misc/NEWS.d/next/Library/2023-05-08-23-01-59.gh-issue-104139.83Tnt-.rst b/Misc/NEWS.d/next/Library/2023-05-08-23-01-59.gh-issue-104139.83Tnt-.rst
new file mode 100644
index 00000000000000..145e75f6dea6f4
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2023-05-08-23-01-59.gh-issue-104139.83Tnt-.rst
@@ -0,0 +1,3 @@
+Teach :func:`urllib.parse.unsplit` to retain the ``"//"`` when assembling
+``itms-services://?action=generate-bugs`` style `Apple Platform Deployment
+<https://support.apple.com/en-gb/guide/deployment/depce7cefc4d/web>`_ URLs.