diff --git a/docs/change_log/index.md b/docs/change_log/index.md
index 584583ff..ee2445cb 100644
--- a/docs/change_log/index.md
+++ b/docs/change_log/index.md
@@ -3,6 +3,10 @@ title: Change Log
 Python-Markdown Change Log
 =========================
 
+*under development*: version 3.4.4 (a bug-fix release).
+
+* Add a special case for initial 's to smarty extension (#1305).
+
 March 23, 2023: version 3.4.3 (a bug-fix release).
 
 * Restore console script (#1327).
diff --git a/markdown/extensions/smarty.py b/markdown/extensions/smarty.py
index 15e57848..f03169e0 100644
--- a/markdown/extensions/smarty.py
+++ b/markdown/extensions/smarty.py
@@ -139,7 +139,7 @@
 
 # Single closing quotes:
 closingSingleQuotesRegex = r"(?<=%s)'(?!\s|s\b|\d)" % closeClass
-closingSingleQuotesRegex2 = r"(?<=%s)'(\s|s\b)" % closeClass
+closingSingleQuotesRegex2 = r"'(\s|s\b)"
 
 # All remaining quotes should be opening ones
 remainingSingleQuotesRegex = r"'"
diff --git a/tests/test_syntax/extensions/test_smarty.py b/tests/test_syntax/extensions/test_smarty.py
index f2d074dd..aeb09884 100644
--- a/tests/test_syntax/extensions/test_smarty.py
+++ b/tests/test_syntax/extensions/test_smarty.py
@@ -64,6 +64,10 @@ def test_basic(self):
             '"Ellipsis within quotes..."',
             '<p>&ldquo;Ellipsis within quotes&hellip;&rdquo;</p>'
         )
+        self.assertMarkdownRenders(
+            "*Custer*'s Last Stand",
+            "<p><em>Custer</em>&rsquo;s Last Stand</p>"
+        )
 
     def test_years(self):
         self.assertMarkdownRenders("1440--80's", '<p>1440&ndash;80&rsquo;s</p>')