diff --git a/Misc/NEWS.d/next/Windows/2023-01-09-23-03-57.gh-issue-100180.b5phrg.rst b/Misc/NEWS.d/next/Windows/2023-01-09-23-03-57.gh-issue-100180.b5phrg.rst
new file mode 100644
index 00000000000000..5b0f42568d92fa
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2023-01-09-23-03-57.gh-issue-100180.b5phrg.rst
@@ -0,0 +1 @@
+Update Windows installer to OpenSSL 1.1.1s
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 57628396ed06a1..8f7a6aae7833ef 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -49,7 +49,7 @@ echo.Fetching external libraries...
 
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.8
-if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1n
+if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1s
 set libraries=%libraries%                                       sqlite-3.31.1.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tcl-core-8.6.9.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tk-8.6.9.0
@@ -72,7 +72,7 @@ for %%e in (%libraries%) do (
 echo.Fetching external binaries...
 
 set binaries=
-if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1n
+if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1s
 if NOT "%IncludeTkinter%"=="false" set binaries=%binaries% tcltk-8.6.9.0
 if NOT "%IncludeSSLSrc%"=="false"  set binaries=%binaries% nasm-2.11.06
 
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 1226d623831ba0..53d106935b5d5d 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -49,8 +49,8 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.31.1.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.8\</bz2Dir>
     <lzmaDir>$(ExternalsDir)xz-5.2.2\</lzmaDir>
-    <opensslDir>$(ExternalsDir)openssl-1.1.1n\</opensslDir>
-    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1n\$(ArchName)\</opensslOutDir>
+    <opensslDir>$(ExternalsDir)openssl-1.1.1s\</opensslDir>
+    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1s\$(ArchName)\</opensslOutDir>
     <opensslIncludeDir>$(opensslOutDir)include</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
     <zlibDir>$(ExternalsDir)\zlib-1.2.12\</zlibDir>