diff --git a/Doc/tools/removed-ids.txt b/Doc/tools/removed-ids.txt
index 3801e6d31199d69..059cbb9a8465496 100644
--- a/Doc/tools/removed-ids.txt
+++ b/Doc/tools/removed-ids.txt
@@ -16,6 +16,8 @@ deprecations/index.html: pending-removal-in-python-3-16
 deprecations/index.html: c-api-pending-removal-in-python-3-15
 deprecations/index.html: c-api-pending-removal-in-python-3-16
 
+tutorial/modules.html: packages-in-multiple-directories
+
 # Removed libmpdec
 using/configure.html: cmdoption-with-system-libmpdec
 
diff --git a/Doc/tutorial/modules.rst b/Doc/tutorial/modules.rst
index f8105cd5441fec2..46a226be606aeba 100644
--- a/Doc/tutorial/modules.rst
+++ b/Doc/tutorial/modules.rst
@@ -584,20 +584,6 @@ Since the main module does not have a package, modules intended for use
 as the main module of a Python application must always use absolute imports.
 
 
-Packages in Multiple Directories
---------------------------------
-
-Packages support one more special attribute, :attr:`~module.__path__`.  This is
-initialized to be a :term:`sequence` of strings containing the name of the
-directory holding the
-package's :file:`__init__.py` before the code in that file is executed.  This
-variable can be modified; doing so affects future searches for modules and
-subpackages contained in the package.
-
-While this feature is not often needed, it can be used to extend the set of
-modules found in a package.
-
-
 .. rubric:: Footnotes
 
 .. [#] In fact function definitions are also 'statements' that are 'executed'; the
diff --git a/Lib/test/test_re.py b/Lib/test/test_re.py
index d086fd521e73b59..ff106c1b3415668 100644
--- a/Lib/test/test_re.py
+++ b/Lib/test/test_re.py
@@ -2145,6 +2145,28 @@ def test_locale_flag(self):
         self.assertRaises(ValueError, re.compile, b'(?a)', re.LOCALE)
         self.assertRaises(re.PatternError, re.compile, b'(?aL)')
 
+    def test_locale_ignorecase_negated_set(self):
+        IL = re.LOCALE | re.IGNORECASE
+        # [bc] matches b'B', so [^bc] must not.
+        self.assertTrue(re.fullmatch(rb'[bc]', b'B', IL))
+        self.assertIsNone(re.fullmatch(rb'[^bc]', b'B', IL))
+        self.assertIsNone(re.fullmatch(rb'[^b-c]', b'C', IL))
+        self.assertIsNone(re.fullmatch(rb'[^bc]', b'c', IL))
+        self.assertTrue(re.fullmatch(rb'[^bc]', b'a', IL))
+        # A one-member set compiles to NOT_LITERAL_LOC_IGNORE.
+        self.assertIsNone(re.fullmatch(rb'[^b]', b'B', IL))
+        self.assertTrue(re.fullmatch(rb'[^b]', b'a', IL))
+        self.assertIsNone(re.fullmatch(rb'[^\wq]', b'Q', IL))
+        # A sparse set compiles to a bitmap instead of ranges.
+        self.assertTrue(re.fullmatch(rb'[ace]', b'C', IL))
+        self.assertIsNone(re.fullmatch(rb'[^ace]', b'C', IL))
+        self.assertTrue(re.fullmatch(rb'[^ace]', b'b', IL))
+        # An alternation folded into a set puts NEGATE in the middle of it.
+        self.assertIsNone(re.fullmatch(rb'(?:a|[^bc])', b'B', IL))
+        self.assertTrue(re.fullmatch(rb'(?:a|[^bc])', b'A', IL))
+        self.assertIsNone(re.fullmatch(rb'\w(?<!b)', b'B', IL))
+        self.assertTrue(re.fullmatch(rb'\w(?<!b)', b'A', IL))
+
     def test_scoped_flags(self):
         self.assertTrue(re.match(r'(?i:a)b', 'Ab'))
         self.assertIsNone(re.match(r'(?i:a)b', 'aB'))
diff --git a/Mac/BuildScript/build-installer.py b/Mac/BuildScript/build-installer.py
index 16ad3fd111f65d6..f22256c1f506cb9 100755
--- a/Mac/BuildScript/build-installer.py
+++ b/Mac/BuildScript/build-installer.py
@@ -246,9 +246,9 @@ def library_recipes():
 
     result.extend([
           dict(
-              name="OpenSSL 3.5.7",
-              url="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/openssl/openssl/releases/download/openssl-3.5.7/openssl-3.5.7.tar.gz",
-              checksum="a8c0d28a529ca480f9f36cf5792e2cd21984552a3c8e4aa11a24aa31aeac98e8",
+              name="OpenSSL 3.5.8",
+              url="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/openssl/openssl/releases/download/openssl-3.5.8/openssl-3.5.8.tar.gz",
+              checksum="a8f84a39918ec6415ce765d9b429d313ba97b8143169c172e734b9514464f5b2",
               buildrecipe=build_universal_openssl,
               configure=None,
               install=None,
@@ -359,9 +359,9 @@ def library_recipes():
                   ),
           ),
           dict(
-              name="SQLite 3.53.3",
-              url="https://www.sqlite.org/2026/sqlite-autoconf-3530300.tar.gz",
-              checksum="c917d7db16648ec95f714974ace5e5dcf46b7dc70e26600a0a102a3141125db0",
+              name="SQLite 3.53.4",
+              url="https://www.sqlite.org/2026/sqlite-autoconf-3530400.tar.gz",
+              checksum="0e9483900e92cd5de8fd48d16bf9200145a61f7fd5be542a5ac81d8a9516eb9c",
               extra_cflags=('-Os '
                             '-DSQLITE_ENABLE_FTS5 '
                             '-DSQLITE_ENABLE_FTS4 '
diff --git a/Misc/NEWS.d/next/Library/2026-08-27-08-31-29.gh-issue-156444.klcySy.rst b/Misc/NEWS.d/next/Library/2026-08-27-08-31-29.gh-issue-156444.klcySy.rst
new file mode 100644
index 000000000000000..cae73e534c47ddd
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-08-27-08-31-29.gh-issue-156444.klcySy.rst
@@ -0,0 +1,3 @@
+Fix matching of a negated character set in a bytes pattern compiled with both
+:const:`re.IGNORECASE` and :const:`re.LOCALE`.  The case closure is now applied
+to the members of the set, so that ``[^bc]`` no longer matches ``b'B'``.
diff --git a/Misc/NEWS.d/next/macOS/2026-08-27-03-19-21.gh-issue-156369.FKlSGY.rst b/Misc/NEWS.d/next/macOS/2026-08-27-03-19-21.gh-issue-156369.FKlSGY.rst
new file mode 100644
index 000000000000000..e953a92f5a106da
--- /dev/null
+++ b/Misc/NEWS.d/next/macOS/2026-08-27-03-19-21.gh-issue-156369.FKlSGY.rst
@@ -0,0 +1 @@
+Update macOS installer to use OpenSSL 3.5.8.
diff --git a/Misc/NEWS.d/next/macOS/2026-08-27-04-10-12.gh-issue-152023.RNIecw.rst b/Misc/NEWS.d/next/macOS/2026-08-27-04-10-12.gh-issue-152023.RNIecw.rst
new file mode 100644
index 000000000000000..32267c623f6e104
--- /dev/null
+++ b/Misc/NEWS.d/next/macOS/2026-08-27-04-10-12.gh-issue-152023.RNIecw.rst
@@ -0,0 +1 @@
+Update macOS installer builds to SQLite 3.53.4.
diff --git a/Modules/_sre/sre_lib.h b/Modules/_sre/sre_lib.h
index 444cd39d2fed288..fbdbaefb399193d 100644
--- a/Modules/_sre/sre_lib.h
+++ b/Modules/_sre/sre_lib.h
@@ -175,16 +175,71 @@ SRE(charset)(SRE_STATE* state, const SRE_CODE* set, SRE_CODE ch)
     }
 }
 
+/* Like SRE(charset), but matches both locale cases of ch against every set
+   member.  Testing the whole set once per case would complement it before
+   closing it under case instead of after, so that [^bc] matched b'B'.
+   BIGCHARSET and RANGE_UNI_IGNORE are not handled: they never occur in a
+   set of a bytes pattern. */
 LOCAL(int)
 SRE(charset_loc_ignore)(SRE_STATE* state, const SRE_CODE* set, SRE_CODE ch)
 {
     SRE_CODE lo, up;
-    lo = sre_lower_locale(ch);
-    if (SRE(charset)(state, set, lo))
-       return 1;
+    int ok = 1;
 
+    lo = sre_lower_locale(ch);
     up = sre_upper_locale(ch);
-    return up != lo && SRE(charset)(state, set, up);
+    if (up == lo)
+        return SRE(charset)(state, set, lo);
+
+    for (;;) {
+        switch (*set++) {
+
+        case SRE_OP_FAILURE:
+            return !ok;
+
+        case SRE_OP_LITERAL:
+            /* <LITERAL> <code> */
+            if (lo == set[0] || up == set[0])
+                return ok;
+            set++;
+            break;
+
+        case SRE_OP_CATEGORY:
+            /* <CATEGORY> <code> */
+            if (sre_category(set[0], (int) lo) ||
+                sre_category(set[0], (int) up))
+                return ok;
+            set++;
+            break;
+
+        case SRE_OP_CHARSET:
+            /* <CHARSET> <bitmap> */
+            if ((lo < 256 && (set[lo/SRE_CODE_BITS]
+                              & (1u << (lo & (SRE_CODE_BITS-1))))) ||
+                (up < 256 && (set[up/SRE_CODE_BITS]
+                              & (1u << (up & (SRE_CODE_BITS-1))))))
+                return ok;
+            set += 256/SRE_CODE_BITS;
+            break;
+
+        case SRE_OP_RANGE:
+            /* <RANGE> <lower> <upper> */
+            if ((set[0] <= lo && lo <= set[1]) ||
+                (set[0] <= up && up <= set[1]))
+                return ok;
+            set += 2;
+            break;
+
+        case SRE_OP_NEGATE:
+            ok = !ok;
+            break;
+
+        default:
+            /* internal error -- there's not much we can do about it
+               here, so let's just pretend it didn't match... */
+            return 0;
+        }
+    }
 }
 
 LOCAL(Py_ssize_t) SRE(match)(SRE_STATE* state, const SRE_CODE* pattern, int toplevel);