diff --git a/Misc/NEWS.d/next/Windows/2018-04-13-11-39-28.bpo-33184.aEohx0.rst b/Misc/NEWS.d/next/Windows/2018-04-13-11-39-28.bpo-33184.aEohx0.rst
new file mode 100644
index 00000000000..e754155610a
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2018-04-13-11-39-28.bpo-33184.aEohx0.rst
@@ -0,0 +1 @@
+Update Windows installer to OpenSSL 1.0.2o.
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 7c1ed2750a2..cea2068d37b 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -41,7 +41,7 @@ echo.Fetching external libraries...
 
 set libraries=
 set libraries=%libraries%                                    bzip2-1.0.6
-if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2k
+if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2o
 set libraries=%libraries%                                    sqlite-3.21.0.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tcl-core-8.6.6.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tk-8.6.6.0
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 6589a23c7ad..8c398a1f501 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -49,7 +49,7 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.21.0.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <lzmaDir>$(ExternalsDir)xz-5.2.2\</lzmaDir>
-    <opensslDir>$(ExternalsDir)openssl-1.0.2k\</opensslDir>
+    <opensslDir>$(ExternalsDir)openssl-1.0.2o\</opensslDir>
     <opensslIncludeDir>$(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 6f9b9a215c4..04a38672ff9 100644
--- a/PCbuild/readme.txt
+++ b/PCbuild/readme.txt
@@ -177,7 +177,7 @@ _lzma
     Homepage:
         http://tukaani.org/xz/
 _ssl
-    Python wrapper for version 1.0.2k of the OpenSSL secure sockets
+    Python wrapper for version 1.0.2o of the OpenSSL secure sockets
     library, which is built by ssl.vcxproj
     Homepage:
         http://www.openssl.org/