diff --git a/Misc/NEWS b/Misc/NEWS
index d83ac5b..5fff17e 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -148,6 +148,8 @@
 - Issue #26268: Update OS X 10.5+ 32-bit-only installer to build
   and link with OpenSSL 1.0.2f.
 
+- Issue #26268: Update Windows builds to use OpenSSL 1.0.2f.
+
 
 What's New in Python 2.7.11?
 ============================
diff --git a/PC/VS9.0/pyproject.vsprops b/PC/VS9.0/pyproject.vsprops
index 5625f9d..1570615 100644
--- a/PC/VS9.0/pyproject.vsprops
+++ b/PC/VS9.0/pyproject.vsprops
@@ -82,7 +82,7 @@
 	/>
 	<UserMacro
 		Name="opensslDir"
-		Value="$(externalsDir)\openssl-1.0.2d"
+		Value="$(externalsDir)\openssl-1.0.2f"
 	/>
 	<UserMacro
 		Name="tcltkDir"
diff --git a/PC/VS9.0/readme.txt b/PC/VS9.0/readme.txt
index 92d5c8a..90334bf 100644
--- a/PC/VS9.0/readme.txt
+++ b/PC/VS9.0/readme.txt
@@ -132,7 +132,7 @@
 
     Get the source code through
 
-    svn export http://svn.python.org/projects/external/openssl-1.0.2d
+    svn export http://svn.python.org/projects/external/openssl-1.0.2f
 
     ** NOTE: if you use the PCbuild\get_externals.bat approach for
     obtaining external sources then you don't need to manually get the source
@@ -145,11 +145,10 @@
         http://www.nasm.us/
     and add NASM to your PATH.
 
-    You can also install ActivePerl from
+    You will also need ActivePerl from
         http://www.activestate.com/activeperl/
-    if you like to use the official sources instead of the files from
-    python's subversion repository. The svn version contains pre-build
-    makefiles and assembly files.
+    in order to create the necessary makefiles and .asm files for building
+    OpenSSL.
 
     The build process makes sure that no patented algorithms are included.
     For now RC5, MDC2 and IDEA are excluded from the build. You may have
diff --git a/PCbuild/_hashlib.vcxproj b/PCbuild/_hashlib.vcxproj
index 0f98966..5616a1e 100644
--- a/PCbuild/_hashlib.vcxproj
+++ b/PCbuild/_hashlib.vcxproj
@@ -61,7 +61,7 @@
   </PropertyGroup>
   <ItemDefinitionGroup>
     <ClCompile>
-      <AdditionalIncludeDirectories>$(opensslDir)include;%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
+      <AdditionalIncludeDirectories>$(opensslIncludeDir);%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
     </ClCompile>
     <Link>
       <AdditionalDependencies>ws2_32.lib;$(OutDir)libeay$(PyDebugExt).lib;$(OutDir)ssleay$(PyDebugExt).lib;%(AdditionalDependencies)</AdditionalDependencies>
diff --git a/PCbuild/_ssl.vcxproj b/PCbuild/_ssl.vcxproj
index fff23c7..73c9571 100644
--- a/PCbuild/_ssl.vcxproj
+++ b/PCbuild/_ssl.vcxproj
@@ -61,7 +61,7 @@
   </PropertyGroup>
   <ItemDefinitionGroup>
     <ClCompile>
-      <AdditionalIncludeDirectories>$(opensslDir)include;%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
+      <AdditionalIncludeDirectories>$(opensslIncludeDir);%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
     </ClCompile>
     <Link>
       <AdditionalDependencies>ws2_32.lib;crypt32.lib;$(OutDir)libeay$(PyDebugExt).lib;$(OutDir)ssleay$(PyDebugExt).lib;%(AdditionalDependencies)</AdditionalDependencies>
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index ffd1a16..333ee82 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -58,7 +58,7 @@
 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-1.0.2d
+if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2f
 set libraries=%libraries%                                    sqlite-3.6.21
 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/openssl.props b/PCbuild/openssl.props
index 54f3596..e45964e 100644
--- a/PCbuild/openssl.props
+++ b/PCbuild/openssl.props
@@ -15,9 +15,8 @@
     <PreprocessorDefinitions Include="_CRT_SECURE_NO_WARNINGS" />
     <PreprocessorDefinitions Include="_CRT_SECURE_NO_DEPRECATE" />
     <PreprocessorDefinitions Include="OPENSSL_THREADS" />
-    <PreprocessorDefinitions Include="OPENSSL_SYSNAME_WIN32" />
+    <!-- <PreprocessorDefinitions Include="OPENSSL_SYSNAME_WIN32" /> -->
     <PreprocessorDefinitions Include="OPENSSL_IA32_SSE2" />
-    <PreprocessorDefinitions Include="OPENSSL_CPUID_OBJ" />
     <PreprocessorDefinitions Include="SHA1_ASM" />
     <PreprocessorDefinitions Include="SHA256_ASM" />
     <PreprocessorDefinitions Include="SHA512_ASM" />
@@ -51,7 +50,7 @@
     <ClCompile>
       <!-- Suppress 64-bit truncation warnings - they aren't ours to worry about -->
       <DisableSpecificWarnings>4244;4267</DisableSpecificWarnings>
-      <AdditionalIncludeDirectories>$(opensslDir);$(opensslDir)include;$(opensslDir)crypto;$(opensslDir)crypto\asn1;$(opensslDir)crypto\evp;$(opensslDir)crypto\modes</AdditionalIncludeDirectories>
+      <AdditionalIncludeDirectories>$(opensslDir);$(opensslIncludeDir);$(opensslDir)crypto;$(opensslDir)crypto\asn1;$(opensslDir)crypto\evp;$(opensslDir)crypto\modes</AdditionalIncludeDirectories>
       <PreprocessorDefinitions>$(_PreprocessorDefinitionList);%(PreprocessorDefinitions)</PreprocessorDefinitions>
     </ClCompile>
   </ItemDefinitionGroup>
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 08ddaf1..d51e58b 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -35,7 +35,9 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.6.21\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <bsddbDir>$(ExternalsDir)db-4.7.25.0</bsddbDir>
-    <opensslDir>$(ExternalsDir)openssl-1.0.2d\</opensslDir>
+    <opensslDir>$(ExternalsDir)openssl-1.0.2f\</opensslDir>
+    <opensslIncludeDir>$(opensslDir)include32</opensslIncludeDir>
+    <opensslIncludeDir Condition="'$(ArchName)' == 'amd64'">$(opensslDir)include64</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
 
     <!-- Suffix for all binaries when building for debug -->
diff --git a/PCbuild/readme.txt b/PCbuild/readme.txt
index 2388535..c15c364 100644
--- a/PCbuild/readme.txt
+++ b/PCbuild/readme.txt
@@ -183,7 +183,7 @@
     Homepage:
         http://www.bzip.org/
 _ssl
-    Python wrapper for version 1.0.2d of the OpenSSL secure sockets
+    Python wrapper for version 1.0.2f of the OpenSSL secure sockets
     library, which is built by ssl.vcxproj
     Homepage:
         http://www.openssl.org/