diff --git a/Lib/email/_header_value_parser.py b/Lib/email/_header_value_parser.py
index 792072ab9f6128..98512702504677 100644
--- a/Lib/email/_header_value_parser.py
+++ b/Lib/email/_header_value_parser.py
@@ -227,6 +227,12 @@ class Token(TokenList):
     token_type = 'token'
     encode_as_ew = False
 
+    @property
+    def stripped_value(self):
+        for token in self:
+            if token.token_type == 'ttext':
+                return token.value
+
 
 class EncodedWord(TokenList):
     token_type = 'encoded-word'
@@ -734,7 +740,7 @@ def stripped_value(self):
         if token.token_type == 'cfws':
             token = self[1]
         if token.token_type.endswith(
-                ('quoted-string', 'attribute', 'extended-attribute')):
+                ('quoted-string', 'attribute', 'extended-attribute', 'token')):
             return token.stripped_value
         return self.value
 
@@ -2458,8 +2464,8 @@ def get_section(value):
     return section, value
 
 
-def get_value(value):
-    """ quoted-string / attribute
+def get_value(value, *, extended=False):
+    """ quoted-string / token / extended-attribute
 
     """
     v = Value()
@@ -2473,8 +2479,10 @@ def get_value(value):
                                       "only {}".format(leader))
     if value[0] == '"':
         token, value = get_quoted_string(value)
-    else:
+    elif extended:
         token, value = get_extended_attribute(value)
+    else:
+        token, value = get_token(value)
     if leader is not None:
         token[:0] = [leader]
     v.append(token)
@@ -2560,7 +2568,13 @@ def get_parameter(value):
     if value and value[0] == "'":
         token = None
     else:
-        token, value = get_value(value)
+        # Preserve legacy recovery for unencoded *0 continuations using the
+        # charset'language'value form.  Unsectioned parameters are MIME tokens.
+        parse_as_extended = (
+            param.extended or
+            (param.sectioned and param.section_number == 0)
+        )
+        token, value = get_value(value, extended=parse_as_extended)
     if not param.extended or param.section_number > 0:
         if not value or value[0] != "'":
             appendto.append(token)
@@ -2614,7 +2628,7 @@ def get_parameter(value):
             v.append(token)
         token = v
     else:
-        token, value = get_value(value)
+        token, value = get_value(value, extended=True)
     appendto.append(token)
     if remainder is not None:
         assert not value, value
diff --git a/Lib/test/test_email/test_email.py b/Lib/test/test_email/test_email.py
index e40c82bba9af42..c0077f20074141 100644
--- a/Lib/test/test_email/test_email.py
+++ b/Lib/test/test_email/test_email.py
@@ -169,6 +169,14 @@ def test_get_filename(self):
         subpart = msg.get_payload(1)
         eq(subpart.get_filename(), 'dingusfish.gif')
 
+    def test_get_filename_with_unquoted_apostrophe(self):
+        msg = email.message_from_string(
+            "Content-Disposition: attachment; filename=O'Brien.pdf\n",
+            policy=email.policy.default,
+        )
+        self.assertEqual(msg.get_filename(), "O'Brien.pdf")
+        self.assertDefectsEqual(msg['content-disposition'].defects, [])
+
     def test_get_filename_with_name_parameter(self):
         eq = self.assertEqual
 
@@ -1924,6 +1932,23 @@ def test_hierarchy(self):
         self.assertFalse(m0.is_multipart())
         self.assertFalse(m1.is_multipart())
 
+    def test_unquoted_apostrophe_in_boundary(self):
+        msg = email.message_from_string("""\
+Content-Type: multipart/mixed; boundary=abc'def
+
+--abc'def
+Content-Type: text/plain
+
+body
+--abc'def--
+""", policy=email.policy.default)
+        self.assertEqual(msg.get_boundary(), "abc'def")
+        self.assertTrue(msg.is_multipart())
+        self.assertEqual(len(msg.get_payload()), 1)
+        self.assertEqual(msg.get_payload(0).get_payload(), 'body')
+        self.assertDefectsEqual(msg['content-type'].defects, [])
+        self.assertDefectsEqual(msg.defects, [])
+
     def test_empty_multipart_idempotent(self):
         text = """\
 Content-Type: multipart/mixed; boundary="BOUNDARY"
diff --git a/Lib/test/test_email/test_headerregistry.py b/Lib/test/test_email/test_headerregistry.py
index c118fd5e20d048..73d7ace9321416 100644
--- a/Lib/test/test_email/test_headerregistry.py
+++ b/Lib/test/test_email/test_headerregistry.py
@@ -422,6 +422,26 @@ def content_type_as_value(self,
             'text/plain; title="foo"',
             ),
 
+        'unquoted_param_value_with_apostrophe_and_asterisk': (
+            "text/plain; title=O'Brien*notes.txt",
+            'text/plain',
+            'text',
+            'plain',
+            {'title': "O'Brien*notes.txt"},
+            [],
+            'text/plain; title="O\'Brien*notes.txt"',
+            ),
+
+        'unquoted_boundary_with_apostrophe': (
+            "multipart/mixed; boundary=abc'def",
+            'multipart/mixed',
+            'multipart',
+            'mixed',
+            {'boundary': "abc'def"},
+            [],
+            'multipart/mixed; boundary="abc\'def"',
+            ),
+
         'param_value_with_tspecials': (
             'text/plain; title="(bar)foo blue"',
             'text/plain',
@@ -934,6 +954,15 @@ def content_disp_as_value(self,
              ' filename*=utf-8\'\'Schulbesuchsbest%C3%A4ttigung.pdf\n'),
             ),
 
+        'unquoted_filename_with_apostrophe': (
+            "attachment; filename=O'Brien.pdf",
+            'attachment',
+            {'filename': "O'Brien.pdf"},
+            [],
+            'attachment; filename="O\'Brien.pdf"',
+            'Content-Disposition: attachment; filename="O\'Brien.pdf"\n',
+            ),
+
         'parameter_value_with_fws_between_tokens': (
             'attachment; filename="File =?utf-8?q?Name?= With Spaces.pdf"',
             'attachment',
diff --git a/Misc/NEWS.d/next/Library/2026-07-17-21-43-09.gh-issue-153823.RMjgKC.rst b/Misc/NEWS.d/next/Library/2026-07-17-21-43-09.gh-issue-153823.RMjgKC.rst
new file mode 100644
index 00000000000000..2a0fb2d95a42e7
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-07-17-21-43-09.gh-issue-153823.RMjgKC.rst
@@ -0,0 +1,3 @@
+Fix :data:`email.policy.default` to parse apostrophes in unquoted MIME
+parameter values as valid token characters.  This restores attachment
+filename and multipart boundary handling consistent with ``compat32``.