diff --git a/images/win/toolsets/toolset-2016.json b/images/win/toolsets/toolset-2016.json
index a9cf2d1f3..c43976ce0 100644
--- a/images/win/toolsets/toolset-2016.json
+++ b/images/win/toolsets/toolset-2016.json
@@ -132,7 +132,8 @@
                 "4.3.0",
                 "4.4.0",
                 "4.6.0",
-                "4.7.0"
+                "4.7.0",
+                "5.5.0"
             ]
         }
     ],
diff --git a/images/win/toolsets/toolset-2019.json b/images/win/toolsets/toolset-2019.json
index d25e9c6b4..b6e4d1471 100644
--- a/images/win/toolsets/toolset-2019.json
+++ b/images/win/toolsets/toolset-2019.json
@@ -132,7 +132,8 @@
                 "4.3.0",
                 "4.4.0",
                 "4.6.0",
-                "4.7.0"
+                "4.7.0",
+                "5.5.0"
             ]
         }
     ],