diff --git a/Misc/NEWS.d/next/Windows/2023-09-28-17-09-23.gh-issue-109991.CIMftz.rst b/Misc/NEWS.d/next/Windows/2023-09-28-17-09-23.gh-issue-109991.CIMftz.rst
new file mode 100644
index 00000000000..ee988f90863
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2023-09-28-17-09-23.gh-issue-109991.CIMftz.rst
@@ -0,0 +1 @@
+Update Windows build to use OpenSSL 3.0.11.
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 1d3abcc3def..fc43ce2b183 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -53,7 +53,7 @@ echo.Fetching external libraries...
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.8
 if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi-3.4.4
-if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-3.0.10
+if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-3.0.11
 set libraries=%libraries%                                       sqlite-3.42.0.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tcl-core-8.6.13.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tk-8.6.13.0
@@ -76,7 +76,7 @@ echo.Fetching external binaries...
 
 set binaries=
 if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi-3.4.4
-if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-3.0.10
+if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-3.0.11
 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 94faa8221ea..35c6e92be45 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -74,8 +74,8 @@
     <libffiDir Condition="$(libffiDir) == ''">$(ExternalsDir)libffi-3.4.4\</libffiDir>
     <libffiOutDir Condition="$(libffiOutDir) == ''">$(libffiDir)$(ArchName)\</libffiOutDir>
     <libffiIncludeDir Condition="$(libffiIncludeDir) == ''">$(libffiOutDir)include</libffiIncludeDir>
-    <opensslDir Condition="$(opensslDir) == ''">$(ExternalsDir)openssl-3.0.10\</opensslDir>
-    <opensslOutDir Condition="$(opensslOutDir) == ''">$(ExternalsDir)openssl-bin-3.0.10\$(ArchName)\</opensslOutDir>
+    <opensslDir Condition="$(opensslDir) == ''">$(ExternalsDir)openssl-3.0.11\</opensslDir>
+    <opensslOutDir Condition="$(opensslOutDir) == ''">$(ExternalsDir)openssl-bin-3.0.11\$(ArchName)\</opensslOutDir>
     <opensslIncludeDir Condition="$(opensslIncludeDir) == ''">$(opensslOutDir)include</opensslIncludeDir>
     <nasmDir Condition="$(nasmDir) == ''">$(ExternalsDir)\nasm-2.11.06\</nasmDir>
     <zlibDir Condition="$(zlibDir) == ''">$(ExternalsDir)\zlib-1.2.13\</zlibDir>