diff --git a/Lib/logging/handlers.py b/Lib/logging/handlers.py
index fb6b5f3b411b22..acb31f38251f74 100644
--- a/Lib/logging/handlers.py
+++ b/Lib/logging/handlers.py
@@ -1127,29 +1127,36 @@ def emit(self, record):
             msg['Subject'] = self.getSubject(record)
             msg['Date'] = email.utils.localtime()
             msg.set_content(self.format(record))
-            if self.username:
-                if self.secure is not None:
-                    import ssl
-
-                    try:
-                        keyfile = self.secure[0]
-                    except IndexError:
-                        keyfile = None
-
-                    try:
-                        certfile = self.secure[1]
-                    except IndexError:
-                        certfile = None
-
-                    context = ssl._create_stdlib_context(
-                        certfile=certfile, keyfile=keyfile
-                    )
-                    smtp.ehlo()
-                    smtp.starttls(context=context)
-                    smtp.ehlo()
-                smtp.login(self.username, self.password)
-            smtp.send_message(msg)
-            smtp.quit()
+            try:
+                if self.username:
+                    if self.secure is not None:
+                        import ssl
+
+                        try:
+                            keyfile = self.secure[0]
+                        except IndexError:
+                            keyfile = None
+
+                        try:
+                            certfile = self.secure[1]
+                        except IndexError:
+                            certfile = None
+
+                        context = ssl._create_stdlib_context(
+                            certfile=certfile, keyfile=keyfile
+                        )
+                        smtp.ehlo()
+                        smtp.starttls(context=context)
+                        smtp.ehlo()
+                    smtp.login(self.username, self.password)
+                smtp.send_message(msg)
+                smtp.quit()
+            except Exception:
+                try:
+                    smtp.close()
+                except Exception:
+                    pass
+                raise
         except Exception:
             self.handleError(record)
 
diff --git a/Lib/test/test_logging.py b/Lib/test/test_logging.py
index 7cd0df3ea0b62d..2e3f8bdcad78a1 100644
--- a/Lib/test/test_logging.py
+++ b/Lib/test/test_logging.py
@@ -1171,6 +1171,25 @@ def test_basic(self):
         self.assertEndsWith(data, '\n\nHello \u2713')
         h.close()
 
+    def test_connection_closed_on_send_failure(self):
+        handler = logging.handlers.SMTPHandler(
+            ("localhost", 25),
+            "me@example.com",
+            "you@example.com",
+            "subject",
+            timeout=self.TIMEOUT,
+        )
+        record = logging.makeLogRecord({"msg": "hello"})
+
+        smtp = unittest.mock.Mock()
+        smtp.send_message.side_effect = OSError("send failed")
+
+        with unittest.mock.patch("smtplib.SMTP", return_value=smtp):
+            with support.captured_stderr():
+                handler.emit(record)
+
+        smtp.close.assert_called_once()
+
     def process_message(self, *args):
         self.messages.append(args)
         self.handled.set()
diff --git a/Misc/NEWS.d/next/Library/2026-08-17-10-12-27.gh-issue-155946.NCtsd4.rst b/Misc/NEWS.d/next/Library/2026-08-17-10-12-27.gh-issue-155946.NCtsd4.rst
new file mode 100644
index 00000000000000..73e89f2638d2d7
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-08-17-10-12-27.gh-issue-155946.NCtsd4.rst
@@ -0,0 +1,2 @@
+:mod:`logging`: ensure that :class:`logging.handlesr.SMTPHandler`
+correctly releases resources on SMTP connection failures.