diff --git a/Misc/NEWS b/Misc/NEWS
index 407bf0fffe5220..fca1540a55019c 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -112,6 +112,8 @@ Documentation
 Build
 -----
 
+- bpo-29572: Update Windows build and OS X installers to use OpenSSL 1.0.2k.
+
 - Issue #28768: Fix implicit declaration of function _setmode. Patch by
   Masayuki Yamamoto
 
diff --git a/PC/VS9.0/pyproject.vsprops b/PC/VS9.0/pyproject.vsprops
index 8b06f0c7dc1524..41aebaf883fa81 100644
--- a/PC/VS9.0/pyproject.vsprops
+++ b/PC/VS9.0/pyproject.vsprops
@@ -82,7 +82,7 @@
 	/>
 	<UserMacro
 		Name="opensslDir"
-		Value="$(externalsDir)\openssl-1.0.2j"
+		Value="$(externalsDir)\openssl-1.0.2k"
 	/>
 	<UserMacro
 		Name="tcltkDir"
diff --git a/PC/VS9.0/readme.txt b/PC/VS9.0/readme.txt
index 10bfd99d4122dd..55dda781d1278b 100644
--- a/PC/VS9.0/readme.txt
+++ b/PC/VS9.0/readme.txt
@@ -132,7 +132,7 @@ _ssl
 
     Get the source code through
 
-    svn export http://svn.python.org/projects/external/openssl-1.0.2j
+    svn export http://svn.python.org/projects/external/openssl-1.0.2k
 
     ** NOTE: if you use the PCbuild\get_externals.bat approach for
     obtaining external sources then you don't need to manually get the source
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 387d9aed9c9bf3..21dcaa4d58f963 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -58,7 +58,7 @@ set libraries=
 set libraries=%libraries%                                    bzip2-1.0.6
 if NOT "%IncludeBsddb%"=="false" set libraries=%libraries%   db-4.7.25.0
 if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     nasm-2.11.06
-if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2j
+if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2k
 set libraries=%libraries%                                    sqlite-3.8.11.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tcl-8.5.15.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tk-8.5.15.0
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 21ea5fa2a8d01f..486a7c9914b888 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -35,7 +35,7 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.8.11.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <bsddbDir>$(ExternalsDir)db-4.7.25.0</bsddbDir>
-    <opensslDir>$(ExternalsDir)openssl-1.0.2j\</opensslDir>
+    <opensslDir>$(ExternalsDir)openssl-1.0.2k\</opensslDir>
     <opensslIncludeDir>$(opensslDir)include32</opensslIncludeDir>
     <opensslIncludeDir Condition="'$(ArchName)' == 'amd64'">$(opensslDir)include64</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
diff --git a/PCbuild/readme.txt b/PCbuild/readme.txt
index 67adb7f0a02496..9438b3991263a3 100644
--- a/PCbuild/readme.txt
+++ b/PCbuild/readme.txt
@@ -183,7 +183,7 @@ _bz2
     Homepage:
         http://www.bzip.org/
 _ssl
-    Python wrapper for version 1.0.2j of the OpenSSL secure sockets
+    Python wrapper for version 1.0.2k of the OpenSSL secure sockets
     library, which is built by ssl.vcxproj
     Homepage:
         http://www.openssl.org/