diff --git a/build/yamls/antrea-windows-with-ovs.yml b/build/yamls/antrea-windows-with-ovs.yml
index ffc1e1bb0dd..6c22a78808d 100644
--- a/build/yamls/antrea-windows-with-ovs.yml
+++ b/build/yamls/antrea-windows-with-ovs.yml
@@ -1,5 +1,24 @@
 apiVersion: v1
 data:
+  Install-OVSDriver-Containerd.ps1: |
+    $ErrorActionPreference = "Stop"
+    mkdir -force c:/openvswitch/driver
+    $mountPath = $env:CONTAINER_SANDBOX_MOUNT_POINT
+    $mountPath = ($mountPath.Replace('\', '/')).TrimEnd('/')
+    $OVSDriverDir = "$mountPath\openvswitch\driver"
+
+    # Check if OVSExt driver is already installed
+    $driverStatus = netcfg -q ovsext
+    if ($driverStatus -like '*not installed*') {
+      # Install OVS Driver
+      $result = netcfg -l $OVSDriverDir/ovsext.inf -c s -i OVSExt
+      if ($result -like '*failed*') {
+        Write-Host "Failed to install OVSExt driver: $result"
+        exit 1
+      } else {
+        Write-Host "OVSExt driver has been installed"
+      }
+    }
   Install-WindowsCNI-Containerd.ps1: |
     $ErrorActionPreference = "Stop";
     mkdir -force c:/var/log/antrea
@@ -45,14 +64,7 @@ data:
     $mountPath = $env:CONTAINER_SANDBOX_MOUNT_POINT
     $mountPath = ($mountPath.Replace('\', '/')).TrimEnd('/')
     $env:PATH = $env:PATH + ";$mountPath/Windows/System32;$mountPath/openvswitch/usr/bin;$mountPath/openvswitch/usr/sbin"
-    $OVSDriverDir="$mountPath\openvswitch\driver"
-
-    # Check if OVSExt driver is already installed
-    $driverStatus = netcfg -q ovsext
-    if ($driverStatus -like '*not installed*') {
-      # Install OVS Driver
-      netcfg -l $OVSDriverDir/ovsext.inf -c s -i OVSExt
-    }
+    $OVSDriverDir = "$mountPath\openvswitch\driver"
 
     # Configure OVS processes
     $OVS_DB_SCHEMA_PATH = "$mountPath/openvswitch/usr/share/openvswitch/vswitch.ovsschema"
@@ -293,7 +305,7 @@ spec:
   template:
     metadata:
       annotations:
-        checksum/agent-windows: bb43d8d5840ffd71ff946d44052fefc5bd88ca5ad58ac5048d85a5cf26a7ef13
+        checksum/agent-windows: 8c254572ffa923c76be75d5d6b235a82e65d3e0da4a4ce969dac0bbcababa3c4
         checksum/windows-config: 6ff4f8bd0b310ebe4d4612bdd9697ffb3d79e0e0eab3936420417dd5a8fc128d
         microsoft.com/hostprocess-inherit-user: "true"
       labels:
@@ -376,6 +388,17 @@ spec:
           readOnly: true
         - mountPath: /var/lib/antrea-windows
           name: antrea-agent-windows
+      - args:
+        - -file
+        - $env:CONTAINER_SANDBOX_MOUNT_POINT/var/lib/antrea-windows/Install-OVSDriver-Containerd.ps1
+        command:
+        - powershell
+        image: antrea/antrea-windows:latest
+        imagePullPolicy: IfNotPresent
+        name: install-ovs-driver
+        volumeMounts:
+        - mountPath: /var/lib/antrea-windows
+          name: antrea-agent-windows
       nodeSelector:
         kubernetes.io/os: windows
       priorityClassName: system-node-critical
diff --git a/build/yamls/windows/containerd-with-ovs/conf/Install-OVSDriver-Containerd.ps1 b/build/yamls/windows/containerd-with-ovs/conf/Install-OVSDriver-Containerd.ps1
new file mode 100644
index 00000000000..99c7bab304b
--- /dev/null
+++ b/build/yamls/windows/containerd-with-ovs/conf/Install-OVSDriver-Containerd.ps1
@@ -0,0 +1,18 @@
+$ErrorActionPreference = "Stop"
+mkdir -force c:/openvswitch/driver
+$mountPath = $env:CONTAINER_SANDBOX_MOUNT_POINT
+$mountPath = ($mountPath.Replace('\', '/')).TrimEnd('/')
+$OVSDriverDir = "$mountPath\openvswitch\driver"
+
+# Check if OVSExt driver is already installed
+$driverStatus = netcfg -q ovsext
+if ($driverStatus -like '*not installed*') {
+  # Install OVS Driver
+  $result = netcfg -l $OVSDriverDir/ovsext.inf -c s -i OVSExt
+  if ($result -like '*failed*') {
+    Write-Host "Failed to install OVSExt driver: $result"
+    exit 1
+  } else {
+    Write-Host "OVSExt driver has been installed"
+  }
+}
diff --git a/build/yamls/windows/containerd-with-ovs/conf/Run-AntreaOVS-Containerd.ps1 b/build/yamls/windows/containerd-with-ovs/conf/Run-AntreaOVS-Containerd.ps1
index 13f0f9c4f06..ee0747ada51 100644
--- a/build/yamls/windows/containerd-with-ovs/conf/Run-AntreaOVS-Containerd.ps1
+++ b/build/yamls/windows/containerd-with-ovs/conf/Run-AntreaOVS-Containerd.ps1
@@ -2,14 +2,7 @@ $ErrorActionPreference = "Stop"
 $mountPath = $env:CONTAINER_SANDBOX_MOUNT_POINT
 $mountPath = ($mountPath.Replace('\', '/')).TrimEnd('/')
 $env:PATH = $env:PATH + ";$mountPath/Windows/System32;$mountPath/openvswitch/usr/bin;$mountPath/openvswitch/usr/sbin"
-$OVSDriverDir="$mountPath\openvswitch\driver"
-
-# Check if OVSExt driver is already installed
-$driverStatus = netcfg -q ovsext
-if ($driverStatus -like '*not installed*') {
-  # Install OVS Driver
-  netcfg -l $OVSDriverDir/ovsext.inf -c s -i OVSExt
-}
+$OVSDriverDir = "$mountPath\openvswitch\driver"
 
 # Configure OVS processes
 $OVS_DB_SCHEMA_PATH = "$mountPath/openvswitch/usr/share/openvswitch/vswitch.ovsschema"
diff --git a/build/yamls/windows/containerd-with-ovs/containerd-with-ovs.yml b/build/yamls/windows/containerd-with-ovs/containerd-with-ovs.yml
index d4df7b9a5fa..ae9560245cf 100644
--- a/build/yamls/windows/containerd-with-ovs/containerd-with-ovs.yml
+++ b/build/yamls/windows/containerd-with-ovs/containerd-with-ovs.yml
@@ -28,3 +28,15 @@ spec:
           - mountPath: /var/log/openvswitch
             name: var-log-antrea
             subPath: openvswitch
+      initContainers:
+      - args:
+        - -file
+        - $env:CONTAINER_SANDBOX_MOUNT_POINT/var/lib/antrea-windows/Install-OVSDriver-Containerd.ps1
+        command:
+        - powershell
+        image: antrea/antrea-windows:latest
+        imagePullPolicy: IfNotPresent
+        name: install-ovs-driver
+        volumeMounts:
+        - mountPath: /var/lib/antrea-windows
+          name: antrea-agent-windows
diff --git a/build/yamls/windows/containerd-with-ovs/kustomization.yml b/build/yamls/windows/containerd-with-ovs/kustomization.yml
index 6326ee0dd0d..2ad451f34aa 100644
--- a/build/yamls/windows/containerd-with-ovs/kustomization.yml
+++ b/build/yamls/windows/containerd-with-ovs/kustomization.yml
@@ -8,6 +8,7 @@ commonLabels:
   app: antrea
 configMapGenerator:
 - files:
+  - conf/Install-OVSDriver-Containerd.ps1
   - conf/Run-AntreaOVS-Containerd.ps1
   - conf/VMSwitchExtension-AntreaAgent-Containerd.ps1
   name: antrea-agent-windows
diff --git a/hack/update-checksum-windows.sh b/hack/update-checksum-windows.sh
index 66f52b2d4d4..078ca94537f 100755
--- a/hack/update-checksum-windows.sh
+++ b/hack/update-checksum-windows.sh
@@ -24,7 +24,8 @@ BASE_CONF_FILES="${WINDOWS_DIR}/base/conf/antrea-agent.conf ${WINDOWS_DIR}/base/
 CONTAINERD_CONF_FILES="${WINDOWS_DIR}/containerd/conf/Install-WindowsCNI-Containerd.ps1 \
     ${WINDOWS_DIR}/containerd/conf/Run-AntreaAgent-Containerd.ps1"
 CONTAINERD_WITH_OVS_CONF_FILES="${WINDOWS_DIR}/containerd-with-ovs/conf/Run-AntreaOVS-Containerd.ps1 \
-    ${WINDOWS_DIR}/containerd-with-ovs/conf/VMSwitchExtension-AntreaAgent-Containerd.ps1"
+    ${WINDOWS_DIR}/containerd-with-ovs/conf/VMSwitchExtension-AntreaAgent-Containerd.ps1 \
+    ${WINDOWS_DIR}/containerd-with-ovs/conf/Install-OVSDriver-Containerd.ps1"
 
 checksum_windows_config=$(cat ${BASE_CONF_FILES} | sha256sum | cut -d " " -f 1)