diff --git a/pkg/release/util/kind_sorter.go b/pkg/release/util/kind_sorter.go
index 22795733c..bc074340f 100644
--- a/pkg/release/util/kind_sorter.go
+++ b/pkg/release/util/kind_sorter.go
@@ -65,12 +65,17 @@ var InstallOrder KindSortOrder = []string{
 	"IngressClass",
 	"Ingress",
 	"APIService",
+	"MutatingWebhookConfiguration",
+	"ValidatingWebhookConfiguration",
 }
 
 // UninstallOrder is the order in which manifests should be uninstalled (by Kind).
 //
 // Those occurring earlier in the list get uninstalled before those occurring later in the list.
 var UninstallOrder KindSortOrder = []string{
+	// For uninstall, we remove validation before mutation to ensure webhooks don't block removal
+	"ValidatingWebhookConfiguration",
+	"MutatingWebhookConfiguration",
 	"APIService",
 	"Ingress",
 	"IngressClass",
diff --git a/pkg/release/util/kind_sorter_test.go b/pkg/release/util/kind_sorter_test.go
index 00d80ecf2..919de24e5 100644
--- a/pkg/release/util/kind_sorter_test.go
+++ b/pkg/release/util/kind_sorter_test.go
@@ -173,6 +173,14 @@ func TestKindSorter(t *testing.T) {
 			Name: "F",
 			Head: &SimpleHead{Kind: "PriorityClass"},
 		},
+		{
+			Name: "M",
+			Head: &SimpleHead{Kind: "MutatingWebhookConfiguration"},
+		},
+		{
+			Name: "V",
+			Head: &SimpleHead{Kind: "ValidatingWebhookConfiguration"},
+		},
 	}
 
 	for _, test := range []struct {
@@ -180,8 +188,8 @@ func TestKindSorter(t *testing.T) {
 		order       KindSortOrder
 		expected    string
 	}{
-		{"install", InstallOrder, "FaAbcC3deEf1gh2iIjJkKlLmnopqrxstuUvw!"},
-		{"uninstall", UninstallOrder, "wvUmutsxrqponLlKkJjIi2hg1fEed3CcbAaF!"},
+		{"install", InstallOrder, "FaAbcC3deEf1gh2iIjJkKlLmnopqrxstuUvwMV!"},
+		{"uninstall", UninstallOrder, "VMwvUmutsxrqponLlKkJjIi2hg1fEed3CcbAaF!"},
 	} {
 		var buf bytes.Buffer
 		t.Run(test.description, func(t *testing.T) {