diff --git a/images/macos/scripts/tests/Toolcache.Tests.ps1 b/images/macos/scripts/tests/Toolcache.Tests.ps1
index 31131df0d..98f229ab4 100644
--- a/images/macos/scripts/tests/Toolcache.Tests.ps1
+++ b/images/macos/scripts/tests/Toolcache.Tests.ps1
@@ -57,7 +57,7 @@ Describe "Toolcache" {
         }
     }
 
-    Context "Ruby" -Skip:($os.IsArm64) {
+    Context "Ruby" {
         $rubyDirectory = Join-Path $toolcacheDirectory "Ruby"
         $rubyPackage = $packages | Where-Object { $_.ToolName -eq "Ruby" } | Select-Object -First 1
         $testCase = @{ RubyDirectory = $rubyDirectory }
diff --git a/images/macos/toolsets/toolset-13.json b/images/macos/toolsets/toolset-13.json
index 10c127c4e..837f37d23 100644
--- a/images/macos/toolsets/toolset-13.json
+++ b/images/macos/toolsets/toolset-13.json
@@ -136,14 +136,16 @@
                         "3.10.*",
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 },
                 "arm64": {
                     "versions": [
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 }
             }
diff --git a/images/macos/toolsets/toolset-14.json b/images/macos/toolsets/toolset-14.json
index 33dfe5be9..bef6f2d8e 100644
--- a/images/macos/toolsets/toolset-14.json
+++ b/images/macos/toolsets/toolset-14.json
@@ -234,14 +234,16 @@
                         "3.10.*",
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 },
                 "arm64": {
                     "versions": [
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 }
             }
diff --git a/images/macos/toolsets/toolset-15.json b/images/macos/toolsets/toolset-15.json
index 5d3c259f6..39aab103e 100644
--- a/images/macos/toolsets/toolset-15.json
+++ b/images/macos/toolsets/toolset-15.json
@@ -238,14 +238,16 @@
                         "3.10.*",
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 },
                 "arm64": {
                     "versions": [
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 }
             }
diff --git a/images/macos/toolsets/toolset-26.json b/images/macos/toolsets/toolset-26.json
index 0a346018b..e7566e461 100644
--- a/images/macos/toolsets/toolset-26.json
+++ b/images/macos/toolsets/toolset-26.json
@@ -140,7 +140,8 @@
                     "versions": [
                         "3.11.*",
                         "3.12.*",
-                        "3.13.*"
+                        "3.13.*",
+                        "3.14.*"
                     ]
                 }
             }
diff --git a/images/ubuntu/toolsets/toolset-2204.json b/images/ubuntu/toolsets/toolset-2204.json
index 9e1fa436c..8285f0b79 100644
--- a/images/ubuntu/toolsets/toolset-2204.json
+++ b/images/ubuntu/toolsets/toolset-2204.json
@@ -11,7 +11,8 @@
                 "3.10.*",
                 "3.11.*",
                 "3.12.*",
-                "3.13.*"
+                "3.13.*",
+                "3.14.*"
             ]
         },
         {
diff --git a/images/ubuntu/toolsets/toolset-2404.json b/images/ubuntu/toolsets/toolset-2404.json
index ba15b375c..aa80e73ac 100644
--- a/images/ubuntu/toolsets/toolset-2404.json
+++ b/images/ubuntu/toolsets/toolset-2404.json
@@ -11,7 +11,8 @@
                 "3.10.*",
                 "3.11.*",
                 "3.12.*",
-                "3.13.*"
+                "3.13.*",
+                "3.14.*"
             ]
         },
         {
diff --git a/images/windows/toolsets/toolset-2019.json b/images/windows/toolsets/toolset-2019.json
index 2cd0a4ce4..f11d4c68b 100644
--- a/images/windows/toolsets/toolset-2019.json
+++ b/images/windows/toolsets/toolset-2019.json
@@ -21,7 +21,8 @@
                 "3.10.*",
                 "3.11.*",
                 "3.12.*",
-                "3.13.*"
+                "3.13.*",
+                "3.14.*"
             ],
             "default": "3.9.*"
         },
diff --git a/images/windows/toolsets/toolset-2022.json b/images/windows/toolsets/toolset-2022.json
index 7d8851e3f..cfc7239d3 100644
--- a/images/windows/toolsets/toolset-2022.json
+++ b/images/windows/toolsets/toolset-2022.json
@@ -22,7 +22,8 @@
                 "3.10.*",
                 "3.11.*",
                 "3.12.*",
-                "3.13.*"
+                "3.13.*",
+                "3.14.*"
             ],
             "default": "3.9.*"
         },
diff --git a/images/windows/toolsets/toolset-2025.json b/images/windows/toolsets/toolset-2025.json
index 083c129e2..870006ef0 100644
--- a/images/windows/toolsets/toolset-2025.json
+++ b/images/windows/toolsets/toolset-2025.json
@@ -22,7 +22,8 @@
                 "3.10.*",
                 "3.11.*",
                 "3.12.*",
-                "3.13.*"
+                "3.13.*",
+                "3.14.*"
             ],
             "default": "3.9.*"
         },