diff --git a/azure/defaults.go b/azure/defaults.go
index 02e5508fa5c..0b958629457 100644
--- a/azure/defaults.go
+++ b/azure/defaults.go
@@ -52,7 +52,7 @@ const (
 	// DefaultLinuxGalleryImageName is the default Linux community gallery image definition.
 	DefaultLinuxGalleryImageName = "capi-ubun2-2404"
 	// DefaultWindowsGalleryImageName is the default Windows community gallery image definition.
-	DefaultWindowsGalleryImageName = "capi-win-2019-containerd"
+	DefaultWindowsGalleryImageName = "capi-win-2025-containerd"
 )
 
 const (
@@ -72,7 +72,7 @@ const (
 const (
 	// DefaultWindowsOsAndVersion is the default Windows Server version to use when
 	// generating default images for Windows nodes.
-	DefaultWindowsOsAndVersion = "windows-2019"
+	DefaultWindowsOsAndVersion = "windows-2025"
 )
 
 const (
diff --git a/azure/services/virtualmachineimages/images.go b/azure/services/virtualmachineimages/images.go
index 3a6fcac29ff..5b5d6c72614 100644
--- a/azure/services/virtualmachineimages/images.go
+++ b/azure/services/virtualmachineimages/images.go
@@ -106,7 +106,7 @@ func (s *Service) GetDefaultWindowsImage(ctx context.Context, _, k8sVersion, run
 		if len(match) != 2 {
 			return nil, errors.Errorf("unsupported osAndVersion %s", osAndVersion)
 		}
-		imageName = strings.Replace(imageName, "2019", match[1], 1)
+		imageName = strings.Replace(imageName, "2025", match[1], 1)
 	}
 
 	// Use the Azure Marketplace for specific older versions, to keep "clusterctl upgrade" from rolling new machines.
diff --git a/docs/book/src/developers/development.md b/docs/book/src/developers/development.md
index b55e8019c89..639ff7b8668 100644
--- a/docs/book/src/developers/development.md
+++ b/docs/book/src/developers/development.md
@@ -553,7 +553,7 @@ With the following environment variables defined, you can build a CAPZ cluster f
 | ------------------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
 | `E2E_ARGS`                | `-kubetest.use-ci-artifacts`                                                                                                                                                                             |
 | `KUBERNETES_VERSION`      | `latest` - extract Kubernetes version from https://dl.k8s.io/ci/latest.txt (main's HEAD)<br>`latest-1.<MINOR>` - extract Kubernetes version from dl.k8s.io/ci/latest-1.<MINOR>.txt (release branch's HEAD) |
-| `WINDOWS_SERVER_VERSION`  | Optional, can be `windows-2019` (default) or `windows-2022`                                                                                                                                              |
+| `WINDOWS_SERVER_VERSION`  | Optional, can be `windows-2025` (default) or `windows-2022`                                                                                                                                              |
 | `KUBETEST_WINDOWS_CONFIG` | Default is `upstream-windows.yaml`. CAPZ contains various other configuration recipes in the `test/e2e/data/` directory; you may use any of those by referencing their file names as the value of `KUBETEST_WINDOWS_CONFIG` (e.g., `conformance-fast.yaml`), or you may drop in your own config files into `test/e2e/data/` and reference those.                                                                                                 |
 | `WINDOWS_CONTAINERD_URL`  | Optional, can be any url to a `tar.gz` file containing binaries for containerd in the same format as upstream package                                                                                    |
 
diff --git a/templates/test/ci/cluster-template-prow-ci-version.yaml b/templates/test/ci/cluster-template-prow-ci-version.yaml
index e4deca90a7e..845e0600b9d 100644
--- a/templates/test/ci/cluster-template-prow-ci-version.yaml
+++ b/templates/test/ci/cluster-template-prow-ci-version.yaml
@@ -472,7 +472,7 @@ spec:
         marketplace:
           offer: capi-windows
           publisher: cncf-upstream
-          sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+          sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
           version: latest
       osDisk:
         diskSizeGB: 128
diff --git a/templates/test/ci/cluster-template-prow-machine-pool-ci-version.yaml b/templates/test/ci/cluster-template-prow-machine-pool-ci-version.yaml
index 95955fd588e..2967b91a767 100644
--- a/templates/test/ci/cluster-template-prow-machine-pool-ci-version.yaml
+++ b/templates/test/ci/cluster-template-prow-machine-pool-ci-version.yaml
@@ -478,7 +478,7 @@ spec:
       marketplace:
         offer: capi-windows
         publisher: cncf-upstream
-        sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+        sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
         version: latest
     osDisk:
       diskSizeGB: 128
diff --git a/templates/test/ci/prow-ci-version/patches/machine-deployment-ci-version-windows.yaml b/templates/test/ci/prow-ci-version/patches/machine-deployment-ci-version-windows.yaml
index a0e8936019e..1ab7432533b 100644
--- a/templates/test/ci/prow-ci-version/patches/machine-deployment-ci-version-windows.yaml
+++ b/templates/test/ci/prow-ci-version/patches/machine-deployment-ci-version-windows.yaml
@@ -11,7 +11,7 @@ spec:
         marketplace:
           publisher: cncf-upstream
           offer: capi-windows
-          sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+          sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
           version: "latest"
       identity: UserAssigned
       userAssignedIdentities:
diff --git a/templates/test/ci/prow-machine-pool-ci-version/patches/machine-pool-ci-version-windows.yaml b/templates/test/ci/prow-machine-pool-ci-version/patches/machine-pool-ci-version-windows.yaml
index 07beec81a4c..f9302ccb6b0 100644
--- a/templates/test/ci/prow-machine-pool-ci-version/patches/machine-pool-ci-version-windows.yaml
+++ b/templates/test/ci/prow-machine-pool-ci-version/patches/machine-pool-ci-version-windows.yaml
@@ -11,7 +11,7 @@ spec:
       marketplace:
         publisher: cncf-upstream
         offer: capi-windows
-        sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+        sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
         version: latest
   identity: UserAssigned
   userAssignedIdentities:
diff --git a/templates/test/dev/cluster-template-custom-builds-load.yaml b/templates/test/dev/cluster-template-custom-builds-load.yaml
index 16866fb7343..1a15d2b980f 100644
--- a/templates/test/dev/cluster-template-custom-builds-load.yaml
+++ b/templates/test/dev/cluster-template-custom-builds-load.yaml
@@ -427,7 +427,7 @@ spec:
         marketplace:
           offer: capi-windows
           publisher: cncf-upstream
-          sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+          sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
           version: latest
       osDisk:
         diskSizeGB: 128
diff --git a/templates/test/dev/cluster-template-custom-builds-machine-pool.yaml b/templates/test/dev/cluster-template-custom-builds-machine-pool.yaml
index f4c3f07a3c4..83b2190045e 100644
--- a/templates/test/dev/cluster-template-custom-builds-machine-pool.yaml
+++ b/templates/test/dev/cluster-template-custom-builds-machine-pool.yaml
@@ -433,7 +433,7 @@ spec:
       marketplace:
         offer: capi-windows
         publisher: cncf-upstream
-        sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+        sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
         version: latest
     osDisk:
       diskSizeGB: 128
diff --git a/templates/test/dev/cluster-template-custom-builds.yaml b/templates/test/dev/cluster-template-custom-builds.yaml
index 007e3ac30c2..7bc941a9147 100644
--- a/templates/test/dev/cluster-template-custom-builds.yaml
+++ b/templates/test/dev/cluster-template-custom-builds.yaml
@@ -421,7 +421,7 @@ spec:
         marketplace:
           offer: capi-windows
           publisher: cncf-upstream
-          sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+          sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
           version: latest
       osDisk:
         diskSizeGB: 128
diff --git a/templates/test/dev/custom-builds-machine-pool/patches/machine-pool-deployment-pr-version-windows.yaml b/templates/test/dev/custom-builds-machine-pool/patches/machine-pool-deployment-pr-version-windows.yaml
index a18713bbeb2..cd389da115a 100644
--- a/templates/test/dev/custom-builds-machine-pool/patches/machine-pool-deployment-pr-version-windows.yaml
+++ b/templates/test/dev/custom-builds-machine-pool/patches/machine-pool-deployment-pr-version-windows.yaml
@@ -10,5 +10,5 @@ spec:
       marketplace:
         publisher: cncf-upstream
         offer: capi-windows
-        sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+        sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
         version: latest
diff --git a/templates/test/dev/custom-builds/patches/machine-deployment-pr-version-windows.yaml b/templates/test/dev/custom-builds/patches/machine-deployment-pr-version-windows.yaml
index c153570d2eb..c67a34bbee6 100644
--- a/templates/test/dev/custom-builds/patches/machine-deployment-pr-version-windows.yaml
+++ b/templates/test/dev/custom-builds/patches/machine-deployment-pr-version-windows.yaml
@@ -15,5 +15,5 @@ spec:
         marketplace:
           publisher: cncf-upstream
           offer: capi-windows
-          sku: ${WINDOWS_SERVER_VERSION:=windows-2019}-containerd-gen1
+          sku: ${WINDOWS_SERVER_VERSION:=windows-2025}-containerd-gen1
           version: latest