diff --git a/Misc/NEWS b/Misc/NEWS
index 9825e090071..9f79a6f6d2d 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -47,6 +47,8 @@ IDLE
 Build
 -----
 
+- Issue #26930: Update Windows builds to use OpenSSL 1.0.2h.
+
 - Issue #23968: Rename the platform directory from plat-$(MACHDEP) to
   plat-$(PLATFORM_TRIPLET).
   Rename the config directory (LIBPL) from config-$(LDVERSION) to
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 63ba282d8ba..9b2a084bc2f 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -54,7 +54,7 @@ echo.Fetching external libraries...
 set libraries=
 set libraries=%libraries%                                    bzip2-1.0.6
 if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     nasm-2.11.06
-if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2g
+if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2h
 set libraries=%libraries%                                    sqlite-3.8.11.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tcl-core-8.6.4.2
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tk-8.6.4.2
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 07acfaba7b2..843771d3f00 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -41,7 +41,7 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.8.11.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <lzmaDir>$(ExternalsDir)xz-5.0.5\</lzmaDir>
-    <opensslDir>$(ExternalsDir)openssl-1.0.2g\</opensslDir>
+    <opensslDir>$(ExternalsDir)openssl-1.0.2h\</opensslDir>
     <opensslIncludeDir>$(opensslDir)include32</opensslIncludeDir>
     <opensslIncludeDir Condition="'$(ArchName)' == 'amd64'">$(opensslDir)include64</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
diff --git a/PCbuild/readme.txt b/PCbuild/readme.txt
index ba269270099..2046af9d3c9 100644
--- a/PCbuild/readme.txt
+++ b/PCbuild/readme.txt
@@ -169,7 +169,7 @@ _lzma
     Homepage:
         http://tukaani.org/xz/
 _ssl
-    Python wrapper for version 1.0.2g of the OpenSSL secure sockets
+    Python wrapper for version 1.0.2h of the OpenSSL secure sockets
     library, which is built by ssl.vcxproj
     Homepage:
         http://www.openssl.org/