diff --git a/Misc/NEWS b/Misc/NEWS
index b17ad90a013..47e3d05a1be 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -127,6 +127,11 @@ Tests
   determine the candidate encoding for the test regex (allowing it to correctly
   skip the test when the default locale encoding is a multi-byte encoding)
 
+Build
+-----
+
+- bpo-29572: Update Windows build and OS X installers to use OpenSSL 1.0.2k.
+
 
 What's New in Python 3.5.3?
 ===========================
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 1c3cdee2c4b..dfaf5496a2b 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -54,7 +54,7 @@ echo.Fetching external libraries...
 set libraries=
 set libraries=%libraries%                                    bzip2-1.0.6
 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-core-8.6.4.2
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tk-8.6.4.2
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 1553731d1fe..0a6fd2a6513 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -46,7 +46,7 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.8.11.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <lzmaDir>$(ExternalsDir)xz-5.0.5\</lzmaDir>
-    <opensslDir>$(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 24620128ec9..68579256f28 100644
--- a/PCbuild/readme.txt
+++ b/PCbuild/readme.txt
@@ -169,7 +169,7 @@ _lzma
     Homepage:
         http://tukaani.org/xz/
 _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/