diff --git a/Misc/NEWS.d/next/Windows/2023-02-10-14-26-05.gh-issue-101763.RPaj7r.rst b/Misc/NEWS.d/next/Windows/2023-02-10-14-26-05.gh-issue-101763.RPaj7r.rst
new file mode 100644
index 00000000000..e7e5a73afeb
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2023-02-10-14-26-05.gh-issue-101763.RPaj7r.rst
@@ -0,0 +1 @@
+Updates copy of libffi bundled with Windows installs to 3.4.4.
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 2c424517eae..128241393f9 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -52,7 +52,7 @@ echo.Fetching external libraries...
 
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.8
-if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi-3.4.3
+if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi-3.4.4
 if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1t
 set libraries=%libraries%                                       sqlite-3.40.1.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tcl-core-8.6.13.0
@@ -76,7 +76,7 @@ for %%e in (%libraries%) do (
 echo.Fetching external binaries...
 
 set binaries=
-if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi-3.4.3
+if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi-3.4.4
 if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1t
 if NOT "%IncludeTkinter%"=="false" set binaries=%binaries% tcltk-8.6.13.0
 if NOT "%IncludeSSLSrc%"=="false"  set binaries=%binaries% nasm-2.11.06
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 28ee74d8594..7994fbe7cd5 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -71,7 +71,7 @@
     <sqlite3Dir Condition="$(sqlite3Dir) == ''">$(ExternalsDir)sqlite-3.40.1.0\</sqlite3Dir>
     <bz2Dir Condition="$(bz2Dir) == ''">$(ExternalsDir)bzip2-1.0.8\</bz2Dir>
     <lzmaDir Condition="$(lzmaDir) == ''">$(ExternalsDir)xz-5.2.5\</lzmaDir>
-    <libffiDir Condition="$(libffiDir) == ''">$(ExternalsDir)libffi-3.4.3\</libffiDir>
+    <libffiDir Condition="$(libffiDir) == ''">$(ExternalsDir)libffi-3.4.4\</libffiDir>
     <libffiOutDir Condition="$(libffiOutDir) == ''">$(libffiDir)$(ArchName)\</libffiOutDir>
     <libffiIncludeDir Condition="$(libffiIncludeDir) == ''">$(libffiOutDir)include</libffiIncludeDir>
     <opensslDir Condition="$(opensslDir) == ''">$(ExternalsDir)openssl-1.1.1t\</opensslDir>