diff --git a/docs/changelog.md b/docs/changelog.md
index 29ff8d31..fe5aca58 100644
--- a/docs/changelog.md
+++ b/docs/changelog.md
@@ -27,6 +27,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 * Ensure `<center>` is treated like a block-level element (#1481).
 * Ensure that `abbr` extension respects `AtomicString` and does not process
   perceived abbreviations in these strings (#1512).
+* The `smarty` extension correctly renders nested closing quotes (#1514).
 
 ## [3.7] -- 2024-08-16
 
diff --git a/markdown/extensions/smarty.py b/markdown/extensions/smarty.py
index d669e69b..c1817e63 100644
--- a/markdown/extensions/smarty.py
+++ b/markdown/extensions/smarty.py
@@ -134,6 +134,8 @@
 #   <p>He said, "'Quoted' words in a larger quote."</p>
 doubleQuoteSetsRe = r""""'(?=\w)"""
 singleQuoteSetsRe = r"""'"(?=\w)"""
+doubleQuoteSetsRe2 = r'(?<=%s)\'"' % closeClass
+singleQuoteSetsRe2 = r"(?<=%s)\"'" % closeClass
 
 # Special case for decade abbreviations (the '80s):
 decadeAbbrRe = r"(?<!\w)'(?=\d{2}s)"
@@ -143,7 +145,7 @@
 
 # Double closing quotes:
 closingDoubleQuotesRegex = r'"(?=\s)'
-closingDoubleQuotesRegex2 = '(?<=%s)"' % closeClass
+closingDoubleQuotesRegex2 = r'(?<=%s)"' % closeClass
 
 # Get most opening single quotes:
 openingSingleQuotesRegex = r"%s'(?=\w)" % openingQuotesBase
@@ -240,6 +242,8 @@ def educateQuotes(self, md: Markdown) -> None:
             (doubleQuoteStartRe, (rdquo,)),
             (doubleQuoteSetsRe, (ldquo + lsquo,)),
             (singleQuoteSetsRe, (lsquo + ldquo,)),
+            (doubleQuoteSetsRe2, (rsquo + rdquo,)),
+            (singleQuoteSetsRe2, (rdquo + rsquo,)),
             (decadeAbbrRe, (rsquo,)),
             (openingSingleQuotesRegex, (1, lsquo)),
             (closingSingleQuotesRegex, (rsquo,)),
diff --git a/tests/test_syntax/extensions/test_smarty.py b/tests/test_syntax/extensions/test_smarty.py
index 0228ddf0..03585517 100644
--- a/tests/test_syntax/extensions/test_smarty.py
+++ b/tests/test_syntax/extensions/test_smarty.py
@@ -44,6 +44,22 @@ def test_basic(self):
             '\'Quoted "words" in a larger quote.\'',
             '<p>&lsquo;Quoted &ldquo;words&rdquo; in a larger quote.&rsquo;</p>'
         )
+        self.assertMarkdownRenders(
+            '"Quoted words at the \'end.\'"',
+            '<p>&ldquo;Quoted words at the &lsquo;end.&rsquo;&rdquo;</p>'
+        )
+        self.assertMarkdownRenders(
+            '\'Quoted words at the "end."\'',
+            '<p>&lsquo;Quoted words at the &ldquo;end.&rdquo;&rsquo;</p>'
+        )
+        self.assertMarkdownRenders(
+            '(He replied, "She said \'Hello.\'")',
+            '<p>(He replied, &ldquo;She said &lsquo;Hello.&rsquo;&rdquo;)</p>'
+        )
+        self.assertMarkdownRenders(
+            '<span>He replied, "She said \'Hello.\'"</span>',
+            '<p><span>He replied, &ldquo;She said &lsquo;Hello.&rsquo;&rdquo;</span></p>'
+        )
         self.assertMarkdownRenders(
             '"quoted" text and **bold "quoted" text**',
             '<p>&ldquo;quoted&rdquo; text and <strong>bold &ldquo;quoted&rdquo; text</strong></p>'