diff --git a/Misc/NEWS.d/next/Windows/2021-09-03-18-05-21.bpo-45022.bgpD_r.rst b/Misc/NEWS.d/next/Windows/2021-09-03-18-05-21.bpo-45022.bgpD_r.rst
new file mode 100644
index 00000000000..8c19faad771
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2021-09-03-18-05-21.bpo-45022.bgpD_r.rst
@@ -0,0 +1 @@
+Update Windows release to include libffi 3.4.2
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index ea85d98e12b..8fa2993e21f 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -52,7 +52,7 @@ echo.Fetching external libraries...
 
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.6
-if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi-3.3.0
+if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi-3.4.2
 if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1l
 set libraries=%libraries%                                       sqlite-3.35.5.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tcl-core-8.6.11.0
@@ -76,7 +76,7 @@ for %%e in (%libraries%) do (
 echo.Fetching external binaries...
 
 set binaries=
-if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi-3.3.0
+if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi-3.4.2
 if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1l
 if NOT "%IncludeTkinter%"=="false" set binaries=%binaries% tcltk-8.6.11.0
 if NOT "%IncludeSSLSrc%"=="false"  set binaries=%binaries% nasm-2.11.06
diff --git a/PCbuild/libffi.props b/PCbuild/libffi.props
index 975c4a0d355..22c9550e2c0 100644
--- a/PCbuild/libffi.props
+++ b/PCbuild/libffi.props
@@ -6,11 +6,11 @@
     </ClCompile>
     <Link>
       <AdditionalLibraryDirectories>$(libffiOutDir);%(AdditionalLibraryDirectories)</AdditionalLibraryDirectories>
-      <AdditionalDependencies>libffi-7.lib;%(AdditionalDependencies)</AdditionalDependencies>
+      <AdditionalDependencies>libffi-8.lib;%(AdditionalDependencies)</AdditionalDependencies>
     </Link>
   </ItemDefinitionGroup>
   <ItemGroup>
-    <_LIBFFIDLL Include="$(libffiOutDir)\libffi-7.dll" />
+    <_LIBFFIDLL Include="$(libffiOutDir)\libffi-8.dll" />
   </ItemGroup>
   <Target Name="_CopyLIBFFIDLL" Inputs="@(_LIBFFIDLL)" Outputs="@(_LIBFFIDLL->'$(OutDir)%(Filename)%(Extension)')" AfterTargets="Build">
     <Copy SourceFiles="@(_LIBFFIDLL)" DestinationFolder="$(OutDir)" />
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 42c67de4afa..54dcef032e0 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -60,8 +60,8 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.35.5.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <lzmaDir>$(ExternalsDir)xz-5.2.2\</lzmaDir>
-    <libffiDir>$(ExternalsDir)libffi-3.3.0\</libffiDir>
-    <libffiOutDir>$(ExternalsDir)libffi-3.3.0\$(ArchName)\</libffiOutDir>
+    <libffiDir>$(ExternalsDir)libffi-3.4.2\</libffiDir>
+    <libffiOutDir>$(ExternalsDir)libffi-3.4.2\$(ArchName)\</libffiOutDir>
     <libffiIncludeDir>$(libffiOutDir)include</libffiIncludeDir>
     <opensslDir>$(ExternalsDir)openssl-1.1.1l\</opensslDir>
     <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1l\$(ArchName)\</opensslOutDir>