diff --git a/Misc/NEWS b/Misc/NEWS
index 32c608f39dc..149f2a79d03 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -283,8 +283,8 @@ Tests
 Windows
 -------
 
-- Issue #21671, CVE-2014-0224: The bundled version of OpenSSL has been
-  updated to 1.0.1h.
+- Issue #21671, #22160, CVE-2014-0224: The bundled version of OpenSSL has been
+  updated to 1.0.1i.
 
 - Issue #10747: Use versioned labels in the Windows start menu.
   Patch by Olive Kilburn.
diff --git a/PCbuild/pyproject.props b/PCbuild/pyproject.props
index 4bc68fb0adb..0b513ceff8a 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-1.0.1h</opensslDir>
+    <opensslDir>$(externalsDir)\openssl-1.0.1i</opensslDir>
     <tcltkDir>$(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 f3e220552f6..c9db541055d 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-1.0.1h rd /s/q openssl-1.0.1h
+@rem if exist openssl-1.0.1i rd /s/q openssl-1.0.1i
 @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-1.0.1h (
-    rd /s/q openssl-1.0.1g
-    svn export http://svn.python.org/projects/external/openssl-1.0.1h
+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
 )
 
 @rem tcl/tk