From 9eace7e7317502720b4290ec39933220ef95fa6f Mon Sep 17 00:00:00 2001
From: Seth Michael Larson <seth@python.org>
Date: Tue, 3 Nov 2026 13:10:45 -0600
Subject: [PATCH 1/2] gh-161263: Skip MD5 algorithm challenge tests on FIPS

---
 Lib/test/test_urllib2.py                            | 13 +++++++------
 .../2026-11-03-13-12-50.gh-issue-161263.Voe8VM.rst  |  2 ++
 2 files changed, 9 insertions(+), 6 deletions(-)
 create mode 100644 Misc/NEWS.d/next/Tests/2026-11-03-13-12-50.gh-issue-161263.Voe8VM.rst

diff --git a/Lib/test/test_urllib2.py b/Lib/test/test_urllib2.py
index 52f77eaf85e589b..3606c7d9dc66a65 100644
--- a/Lib/test/test_urllib2.py
+++ b/Lib/test/test_urllib2.py
@@ -30,6 +30,11 @@
 
 support.requires_working_socket(module=True)
 
+skip_libssl_fips_mode = unittest.skipIf(
+    support.is_libssl_fips_mode(),
+    "conservative skip due to OpenSSL FIPS mode possible algorithm nerfing",
+)
+
 # XXX
 # Request
 # CacheFTPHandler (hard to write)
@@ -1782,6 +1787,7 @@ def test_proxy_basic_auth(self):
                               "proxy.example.com:3128",
                               )
 
+    @skip_libssl_fips_mode  # Uses MD5 algorithm in challenge
     def test_proxy_digest_auth(self):
         # gh-60299: ProxyDigestAuthHandler must look up credentials using
         # the proxy's authority
@@ -1845,6 +1851,7 @@ def test_proxy_digest_auth_uri(self):
         auth = http_handler.requests[1].get_header("Proxy-authorization")
         self.assertIn('uri="%s"' % request_url, auth)
 
+    @skip_libssl_fips_mode  # Uses MD5 algorithm in challenge
     def test_digest_auth_uses_full_url(self):
         # The non-proxy case must keep using the full request URL (not
         # just the host) for the password lookup, so that sub-URI realm
@@ -2355,12 +2362,6 @@ def test_parse_proxy(self):
         self.assertRaises(ValueError, _parse_proxy, 'file:/ftp.example.com'),
 
 
-skip_libssl_fips_mode = unittest.skipIf(
-    support.is_libssl_fips_mode(),
-    "conservative skip due to OpenSSL FIPS mode possible algorithm nerfing",
-)
-
-
 class TestDigestAuthAlgorithms(unittest.TestCase):
     def setUp(self):
         self.handler = AbstractDigestAuthHandler()
diff --git a/Misc/NEWS.d/next/Tests/2026-11-03-13-12-50.gh-issue-161263.Voe8VM.rst b/Misc/NEWS.d/next/Tests/2026-11-03-13-12-50.gh-issue-161263.Voe8VM.rst
new file mode 100644
index 000000000000000..98c631cc2f663a3
--- /dev/null
+++ b/Misc/NEWS.d/next/Tests/2026-11-03-13-12-50.gh-issue-161263.Voe8VM.rst
@@ -0,0 +1,2 @@
+Skip tests which use MD5 algorithm for WWW-Authenticate challenges when
+libssl is in FIPS mode.

From 2428022d3aa47e409394fe5d70677c0ecd30061a Mon Sep 17 00:00:00 2001
From: Seth Michael Larson <seth@python.org>
Date: Wed, 4 Nov 2026 08:58:32 -0600
Subject: [PATCH 2/2] Need to skip a few more

---
 Lib/lib2to3/Grammar3.11.18.final.0.pickle       | Bin 0 -> 15313 bytes
 .../PatternGrammar3.11.18.final.0.pickle        | Bin 0 -> 1225 bytes
 Lib/test/test_urllib2.py                        |   2 ++
 3 files changed, 2 insertions(+)
 create mode 100644 Lib/lib2to3/Grammar3.11.18.final.0.pickle
 create mode 100644 Lib/lib2to3/PatternGrammar3.11.18.final.0.pickle

diff --git a/Lib/lib2to3/Grammar3.11.18.final.0.pickle b/Lib/lib2to3/Grammar3.11.18.final.0.pickle
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z13VG#F$NaW0B>N3-i)Y=2Xl%>^f3u%bOno#@#?^O4eJ<xZMtk!$L$f*1+zvD7X_|-
iuo@_JyMS7UJBHd%3x#@n>w_*D72)x(u~$6Ny!;2V#C%Zz

literal 0
HcmV?d00001

diff --git a/Lib/test/test_urllib2.py b/Lib/test/test_urllib2.py
index 3606c7d9dc66a65..a5b5a3d706dd409 100644
--- a/Lib/test/test_urllib2.py
+++ b/Lib/test/test_urllib2.py
@@ -1974,6 +1974,7 @@ def check_digest_auth(self, headers, realm):
             self.assertIn('nonce="dcd98b7102dd2f0e8b11d0f600bfb0c093"', auth)
             self.assertIn('opaque="5ccc069c403ebaf9f0171e9517f40e41"', auth)
 
+    @skip_libssl_fips_mode
     def test_digest_auth_multiple_challenges(self):
         realm = "digest@example.com"
         digest = (f'Digest realm="{realm}", '
@@ -2039,6 +2040,7 @@ def test_digest_auth_parse_challenges(self):
             [('Negotiate', 'Negotiate'), ('Bearer', 'Bearer abc=='),
              ('Digest', 'Digest realm="a"')])
 
+    @skip_libssl_fips_mode
     def test_proxy_digest_auth_multiple_challenges(self):
         realm = "digest@example.com"
         digest = (f'Digest realm="{realm}", '