diff --git a/Misc/NEWS b/Misc/NEWS
index 513bdf7f5bb..80721b0e3cc 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -1,4 +1,4 @@
-+++++++++++
++++++++++++
 Python News
 +++++++++++
 
@@ -90,6 +90,10 @@ Build
 
 - Issue #17219: Add library build dir for Python extension cross-builds.
 
+Windows
+-------
+
+- Issue #22644: The bundled version of OpenSSL has been updated to 1.0.1j.
 
 What's New in Python 3.4.2?
 ===========================
diff --git a/PCbuild/pyproject.props b/PCbuild/pyproject.props
index 0b513ceff8a..d1e9dc02a0a 100644
--- a/PCbuild/pyproject.props
+++ b/PCbuild/pyproject.props
@@ -20,7 +20,7 @@
     <sqlite3Dir>$(externalsDir)\sqlite-3.8.3.1</sqlite3Dir>
     <bz2Dir>$(externalsDir)\bzip2-1.0.6</bz2Dir>
     <lzmaDir>$(externalsDir)\xz-5.0.5</lzmaDir>
-    <opensslDir>$(externalsDir)\openssl-1.0.1i</opensslDir>
+    <opensslDir>$(externalsDir)\openssl-1.0.1j</opensslDir>
     <tcltkDir>$(externalsDir)\tcltk</tcltkDir>
     <tcltk64Dir>$(externalsDir)\tcltk64</tcltk64Dir>
     <tcltkLib>$(tcltkDir)\lib\tcl86t.lib;$(tcltkDir)\lib\tk86t.lib</tcltkLib>
diff --git a/Tools/buildbot/external-common.bat b/Tools/buildbot/external-common.bat
index c9db541055d..d1933c25431 100644
--- a/Tools/buildbot/external-common.bat
+++ b/Tools/buildbot/external-common.bat
@@ -11,7 +11,7 @@ cd ..
 @rem if exist tk-8.6.1.0 rd /s/q tk-8.6.1.0
 @rem if exist tix-8.4.3.4 rd /s/q tix-8.4.3.4
 @rem if exist db-4.4.20 rd /s/q db-4.4.20
-@rem if exist openssl-1.0.1i rd /s/q openssl-1.0.1i
+@rem if exist openssl-1.0.1j rd /s/q openssl-1.0.1j
 @rem if exist sqlite-3.7.12 rd /s/q sqlite-3.7.12
 
 @rem bzip
@@ -21,9 +21,9 @@ if not exist bzip2-1.0.6 (
 )
 
 @rem OpenSSL
-if not exist openssl-1.0.1i (
-    rd /s/q openssl-1.0.1h
-    svn export http://svn.python.org/projects/external/openssl-1.0.1i
+if not exist openssl-1.0.1j (
+    rd /s/q openssl-1.0.1i
+    svn export http://svn.python.org/projects/external/openssl-1.0.1j
 )
 
 @rem tcl/tk