diff --git a/images/win/toolsets/toolset-2016.json b/images/win/toolsets/toolset-2016.json
index 7ae5d9adc..e8fde9a6e 100644
--- a/images/win/toolsets/toolset-2016.json
+++ b/images/win/toolsets/toolset-2016.json
@@ -109,7 +109,8 @@
                 "3.1.0",
                 "3.5.0",
                 "3.8.0",
-                "4.3.0"
+                "4.3.0",
+                "4.4.0"
             ]
         }
     ]
diff --git a/images/win/toolsets/toolset-2019.json b/images/win/toolsets/toolset-2019.json
index 9dcf93015..b5ac3ff51 100644
--- a/images/win/toolsets/toolset-2019.json
+++ b/images/win/toolsets/toolset-2019.json
@@ -118,7 +118,8 @@
                 "3.1.0",
                 "3.5.0",
                 "3.8.0",
-                "4.3.0"
+                "4.3.0",
+                "4.4.0"
             ]
         }
     ]