diff --git a/pkg/apis/eksctl.io/v1alpha5/validation.go b/pkg/apis/eksctl.io/v1alpha5/validation.go
index 5cc34b8c57..97bd12a8a9 100644
--- a/pkg/apis/eksctl.io/v1alpha5/validation.go
+++ b/pkg/apis/eksctl.io/v1alpha5/validation.go
@@ -645,7 +645,7 @@ func ValidateNodeGroup(i int, ng *NodeGroup) error {
 		}
 	}
 
-	if ng.AMI != "" && ng.OverrideBootstrapCommand == nil && ng.AMIFamily != NodeImageFamilyBottlerocket {
+	if ng.AMI != "" && ng.OverrideBootstrapCommand == nil && ng.AMIFamily != NodeImageFamilyBottlerocket && !IsWindowsImage(ng.AMIFamily) {
 		return errors.Errorf("%[1]s.overrideBootstrapCommand is required when using a custom AMI (%[1]s.ami)", path)
 	}
 
@@ -681,6 +681,10 @@ func ValidateNodeGroup(i int, ng *NodeGroup) error {
 			return fieldNotSupported("kubeletExtraConfig")
 		}
 
+		if IsWindowsImage(ng.AMIFamily) && ng.OverrideBootstrapCommand != nil {
+			return fieldNotSupported("overrideBootstrapCommand")
+		}
+
 		if ng.AMIFamily == NodeImageFamilyBottlerocket {
 			if ng.PreBootstrapCommands != nil {
 				return fieldNotSupported("preBootstrapCommands")
diff --git a/pkg/apis/eksctl.io/v1alpha5/validation_test.go b/pkg/apis/eksctl.io/v1alpha5/validation_test.go
index f760dbb166..bc66477cc0 100644
--- a/pkg/apis/eksctl.io/v1alpha5/validation_test.go
+++ b/pkg/apis/eksctl.io/v1alpha5/validation_test.go
@@ -146,6 +146,23 @@ var _ = Describe("ClusterConfig validation", func() {
 			ng0.AMIFamily = api.NodeImageFamilyBottlerocket
 			Expect(api.ValidateNodeGroup(0, ng0)).To(Succeed())
 		})
+		It("should not require overrideBootstrapCommand if ami is set and type is Windows", func() {
+			cfg := api.NewClusterConfig()
+			ng0 := cfg.NewNodeGroup()
+			ng0.Name = "node-group"
+			ng0.AMI = "ami-1234"
+			ng0.AMIFamily = api.NodeImageFamilyWindowsServer2019CoreContainer
+			Expect(api.ValidateNodeGroup(0, ng0)).To(Succeed())
+		})
+		It("should throw an error if overrideBootstrapCommand is set and type is Windows", func() {
+			cfg := api.NewClusterConfig()
+			ng0 := cfg.NewNodeGroup()
+			ng0.Name = "node-group"
+			ng0.AMI = "ami-1234"
+			ng0.AMIFamily = api.NodeImageFamilyWindowsServer2019CoreContainer
+			ng0.OverrideBootstrapCommand = aws.String("echo 'yo'")
+			Expect(api.ValidateNodeGroup(0, ng0)).To(MatchError(ContainSubstring("overrideBootstrapCommand is not supported for WindowsServer2019CoreContainer nodegroups")))
+		})
 		It("should accept ami with a overrideBootstrapCommand set", func() {
 			cfg := api.NewClusterConfig()
 			ng0 := cfg.NewNodeGroup()