diff --git a/Misc/NEWS.d/next/Windows/2021-01-05-20-36-40.bpo-41837.bmS7vB.rst b/Misc/NEWS.d/next/Windows/2021-01-05-20-36-40.bpo-41837.bmS7vB.rst
new file mode 100644
index 00000000000..8d4bb34ff90
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2021-01-05-20-36-40.bpo-41837.bmS7vB.rst
@@ -0,0 +1 @@
+Updated Windows installer to include OpenSSL 1.1.1i
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 3bb281904f6..3e9cb0299fc 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -53,7 +53,7 @@ echo.Fetching external libraries...
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.6
 if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi
-if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1g
+if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1i
 set libraries=%libraries%                                       sqlite-3.33.0.0
 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
@@ -77,7 +77,7 @@ echo.Fetching external binaries...
 
 set binaries=
 if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi
-if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1g
+if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1i
 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 acc41a2c017..769dabc5641 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -62,8 +62,8 @@
     <libffiDir>$(ExternalsDir)libffi\</libffiDir>
     <libffiOutDir>$(ExternalsDir)libffi\$(ArchName)\</libffiOutDir>
     <libffiIncludeDir>$(libffiOutDir)include</libffiIncludeDir>
-    <opensslDir>$(ExternalsDir)openssl-1.1.1g\</opensslDir>
-    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1g\$(ArchName)\</opensslOutDir>
+    <opensslDir>$(ExternalsDir)openssl-1.1.1i\</opensslDir>
+    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1i\$(ArchName)\</opensslOutDir>
     <opensslIncludeDir>$(opensslOutDir)include</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
     <zlibDir>$(ExternalsDir)\zlib-1.2.11\</zlibDir>
diff --git a/PCbuild/readme.txt b/PCbuild/readme.txt
index bafd91248a5..c00ee8e3292 100644
--- a/PCbuild/readme.txt
+++ b/PCbuild/readme.txt
@@ -166,7 +166,7 @@ _lzma
     Homepage:
         http://tukaani.org/xz/
 _ssl
-    Python wrapper for version 1.1.1c of the OpenSSL secure sockets
+    Python wrapper for version 1.1.1i of the OpenSSL secure sockets
     library, which is downloaded from our binaries repository at
     https://github.com/python/cpython-bin-deps.