https://github.com/python/cpython/commit/2db4a9d0535af198452136312f9f0b232fa04cf0
commit: 2db4a9d0535af198452136312f9f0b232fa04cf0
branch: 3.12
author: Miss Islington (bot) <31488909+miss-isling...@users.noreply.github.com>
committer: vsajip <vinay_sa...@yahoo.co.uk>
date: 2025-02-10T14:29:57Z
summary:

[3.12] gh-127712: Fix `secure` argument of `logging.handlers.SMTPHandler` 
(GH-127726) (GH-129956)

(cherry picked from commit d7672e5d5a7b9580a72dbe75d3a9e8840bcc604c)

files:
A Misc/NEWS.d/next/Library/2024-12-07-20-33-43.gh-issue-127712.Uzsij4.rst
M Lib/logging/handlers.py

diff --git a/Lib/logging/handlers.py b/Lib/logging/handlers.py
index 73757758af2a2e..0aa7b15ee73be7 100644
--- a/Lib/logging/handlers.py
+++ b/Lib/logging/handlers.py
@@ -1031,7 +1031,8 @@ def __init__(self, mailhost, fromaddr, toaddrs, subject,
         only be used when authentication credentials are supplied. The tuple
         will be either an empty tuple, or a single-value tuple with the name
         of a keyfile, or a 2-value tuple with the names of the keyfile and
-        certificate file. (This tuple is passed to the `starttls` method).
+        certificate file. (This tuple is passed to the
+        `ssl.SSLContext.load_cert_chain` method).
         A timeout in seconds can be specified for the SMTP connection (the
         default is one second).
         """
@@ -1084,8 +1085,23 @@ def emit(self, record):
             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(*self.secure)
+                    smtp.starttls(context=context)
                     smtp.ehlo()
                 smtp.login(self.username, self.password)
             smtp.send_message(msg)
diff --git 
a/Misc/NEWS.d/next/Library/2024-12-07-20-33-43.gh-issue-127712.Uzsij4.rst 
b/Misc/NEWS.d/next/Library/2024-12-07-20-33-43.gh-issue-127712.Uzsij4.rst
new file mode 100644
index 00000000000000..40450cddc956c1
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2024-12-07-20-33-43.gh-issue-127712.Uzsij4.rst
@@ -0,0 +1 @@
+Fix handling of the ``secure`` argument of 
:class:`logging.handlers.SMTPHandler`.

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