diff --git a/staging/src/k8s.io/apiserver/pkg/server/options/encryptionconfig/config_test.go b/staging/src/k8s.io/apiserver/pkg/server/options/encryptionconfig/config_test.go
index 24baf64e80a..58628dac560 100644
--- a/staging/src/k8s.io/apiserver/pkg/server/options/encryptionconfig/config_test.go
+++ b/staging/src/k8s.io/apiserver/pkg/server/options/encryptionconfig/config_test.go
@@ -605,3 +605,206 @@ resources:
 func serviceComparer(_, _ envelope.Service) bool {
 	return true
 }
+
+func TestCBCKeyRotationWithOverlappingProviders(t *testing.T) {
+	testCBCKeyRotationWithProviders(
+		t,
+		`{
+  "kind": "EncryptionConfiguration",
+  "apiVersion": "apiserver.config.k8s.io/v1",
+  "resources": [
+    {
+      "resources": [
+        "ignored"
+      ],
+      "providers": [
+        {
+          "aescbc": {
+            "keys": [
+              {
+                "name": "1",
+                "secret": "Owq7A4JrJpSjrvH8kXkvl4JmOLzvZ6j9BcGRkR8OPQ4="
+              }
+            ]
+          }
+        },
+        {
+          "aescbc": {
+            "keys": [
+              {
+                "name": "2",
+                "secret": "+qcnfOFX3aRXM9PuY7lQXDWYIQ3GWUdBc3nYBo91SCA="
+              }
+            ]
+          }
+        }
+      ]
+    }
+  ]
+}`,
+		"k8s:enc:aescbc:v1:1:",
+		`{
+  "kind": "EncryptionConfiguration",
+  "apiVersion": "apiserver.config.k8s.io/v1",
+  "resources": [
+    {
+      "resources": [
+        "ignored"
+      ],
+      "providers": [
+        {
+          "aescbc": {
+            "keys": [
+              {
+                "name": "2",
+                "secret": "+qcnfOFX3aRXM9PuY7lQXDWYIQ3GWUdBc3nYBo91SCA="
+              }
+            ]
+          }
+        },
+        {
+          "aescbc": {
+            "keys": [
+              {
+                "name": "1",
+                "secret": "Owq7A4JrJpSjrvH8kXkvl4JmOLzvZ6j9BcGRkR8OPQ4="
+              }
+            ]
+          }
+        }
+      ]
+    }
+  ]
+}`,
+		"k8s:enc:aescbc:v1:2:",
+	)
+}
+
+func TestCBCKeyRotationWithoutOverlappingProviders(t *testing.T) {
+	testCBCKeyRotationWithProviders(
+		t,
+		`{
+  "kind": "EncryptionConfiguration",
+  "apiVersion": "apiserver.config.k8s.io/v1",
+  "resources": [
+    {
+      "resources": [
+        "ignored"
+      ],
+      "providers": [
+        {
+          "aescbc": {
+            "keys": [
+              {
+                "name": "A",
+                "secret": "Owq7A4JrJpSjrvH8kXkvl4JmOLzvZ6j9BcGRkR8OPQ4="
+              },
+              {
+                "name": "B",
+                "secret": "+qcnfOFX3aRXM9PuY7lQXDWYIQ3GWUdBc3nYBo91SCA="
+              }
+            ]
+          }
+        }
+      ]
+    }
+  ]
+}`,
+		"k8s:enc:aescbc:v1:A:",
+		`{
+  "kind": "EncryptionConfiguration",
+  "apiVersion": "apiserver.config.k8s.io/v1",
+  "resources": [
+    {
+      "resources": [
+        "ignored"
+      ],
+      "providers": [
+        {
+          "aescbc": {
+            "keys": [
+              {
+                "name": "B",
+                "secret": "+qcnfOFX3aRXM9PuY7lQXDWYIQ3GWUdBc3nYBo91SCA="
+              },
+              {
+                "name": "A",
+                "secret": "Owq7A4JrJpSjrvH8kXkvl4JmOLzvZ6j9BcGRkR8OPQ4="
+              }
+            ]
+          }
+        }
+      ]
+    }
+  ]
+}`,
+		"k8s:enc:aescbc:v1:B:",
+	)
+}
+
+func testCBCKeyRotationWithProviders(t *testing.T, firstEncryptionConfig, firstPrefix, secondEncryptionConfig, secondPrefix string) {
+	p := getTransformerFromEncryptionConfig(t, firstEncryptionConfig)
+
+	context := value.DefaultContext([]byte("authenticated_data"))
+
+	out, err := p.TransformToStorage([]byte("firstvalue"), context)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !bytes.HasPrefix(out, []byte(firstPrefix)) {
+		t.Fatalf("unexpected prefix: %q", out)
+	}
+	from, stale, err := p.TransformFromStorage(out, context)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if stale || !bytes.Equal([]byte("firstvalue"), from) {
+		t.Fatalf("unexpected data: %t %q", stale, from)
+	}
+
+	// verify changing the context fails storage
+	_, _, err = p.TransformFromStorage(out, value.DefaultContext([]byte("incorrect_context")))
+	if err != nil {
+		t.Fatalf("CBC mode does not support authentication: %v", err)
+	}
+
+	// reverse the order, use the second key
+	p = getTransformerFromEncryptionConfig(t, secondEncryptionConfig)
+	from, stale, err = p.TransformFromStorage(out, context)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !stale || !bytes.Equal([]byte("firstvalue"), from) {
+		t.Fatalf("unexpected data: %t %q", stale, from)
+	}
+
+	out, err = p.TransformToStorage([]byte("firstvalue"), context)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !bytes.HasPrefix(out, []byte(secondPrefix)) {
+		t.Fatalf("unexpected prefix: %q", out)
+	}
+	from, stale, err = p.TransformFromStorage(out, context)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if stale || !bytes.Equal([]byte("firstvalue"), from) {
+		t.Fatalf("unexpected data: %t %q", stale, from)
+	}
+}
+
+func getTransformerFromEncryptionConfig(t *testing.T, encryptionConfig string) value.Transformer {
+	t.Helper()
+	transformers, err := ParseEncryptionConfiguration(strings.NewReader(encryptionConfig))
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(transformers) != 1 {
+		t.Fatalf("input config does not have exactly one resource: %s", encryptionConfig)
+	}
+	for _, transformer := range transformers {
+		return transformer
+	}
+	panic("unreachable")
+}
diff --git a/staging/src/k8s.io/apiserver/pkg/storage/value/BUILD b/staging/src/k8s.io/apiserver/pkg/storage/value/BUILD
index 8ddbb531961..48e48840892 100644
--- a/staging/src/k8s.io/apiserver/pkg/storage/value/BUILD
+++ b/staging/src/k8s.io/apiserver/pkg/storage/value/BUILD
@@ -30,6 +30,7 @@ go_library(
     importmap = "k8s.io/kubernetes/vendor/k8s.io/apiserver/pkg/storage/value",
     importpath = "k8s.io/apiserver/pkg/storage/value",
     deps = [
+        "//staging/src/k8s.io/apimachinery/pkg/util/errors:go_default_library",
         "//staging/src/k8s.io/component-base/metrics:go_default_library",
         "//staging/src/k8s.io/component-base/metrics/legacyregistry:go_default_library",
         "//vendor/github.com/prometheus/client_golang/prometheus:go_default_library",
diff --git a/staging/src/k8s.io/apiserver/pkg/storage/value/transformer.go b/staging/src/k8s.io/apiserver/pkg/storage/value/transformer.go
index bb0f1157c34..3bc41cd9a24 100644
--- a/staging/src/k8s.io/apiserver/pkg/storage/value/transformer.go
+++ b/staging/src/k8s.io/apiserver/pkg/storage/value/transformer.go
@@ -22,6 +22,8 @@ import (
 	"fmt"
 	"sync"
 	"time"
+
+	"k8s.io/apimachinery/pkg/util/errors"
 )
 
 func init() {
@@ -129,6 +131,7 @@ func NewPrefixTransformers(err error, transformers ...PrefixTransformer) Transfo
 // the first transformer.
 func (t *prefixTransformers) TransformFromStorage(data []byte, context Context) ([]byte, bool, error) {
 	start := time.Now()
+	var errs []error
 	for i, transformer := range t.transformers {
 		if bytes.HasPrefix(data, transformer.Prefix) {
 			result, stale, err := transformer.Transformer.TransformFromStorage(data[len(transformer.Prefix):], context)
@@ -144,9 +147,48 @@ func (t *prefixTransformers) TransformFromStorage(data []byte, context Context)
 			} else {
 				RecordTransformation("from_storage", string(transformer.Prefix), start, err)
 			}
+
+			// It is valid to have overlapping prefixes when the same encryption provider
+			// is specified multiple times but with different keys (the first provider is
+			// being rotated to and some later provider is being rotated away from).
+			//
+			// Example:
+			//
+			//  {
+			//    "aescbc": {
+			//      "keys": [
+			//        {
+			//          "name": "2",
+			//          "secret": "some key 2"
+			//        }
+			//      ]
+			//    }
+			//  },
+			//  {
+			//    "aescbc": {
+			//      "keys": [
+			//        {
+			//          "name": "1",
+			//          "secret": "some key 1"
+			//        }
+			//      ]
+			//    }
+			//  },
+			//
+			// The transformers for both aescbc configs share the prefix k8s:enc:aescbc:v1:
+			// but a failure in the first one should not prevent a later match from being attempted.
+			// Thus we never short-circuit on a prefix match that results in an error.
+			if err != nil {
+				errs = append(errs, err)
+				continue
+			}
+
 			return result, stale || i != 0, err
 		}
 	}
+	if err := errors.Reduce(errors.NewAggregate(errs)); err != nil {
+		return nil, false, err
+	}
 	RecordTransformation("from_storage", "unknown", start, t.err)
 	return nil, false, t.err
 }
diff --git a/staging/src/k8s.io/apiserver/pkg/storage/value/transformer_test.go b/staging/src/k8s.io/apiserver/pkg/storage/value/transformer_test.go
index 95427586754..08b3275086e 100644
--- a/staging/src/k8s.io/apiserver/pkg/storage/value/transformer_test.go
+++ b/staging/src/k8s.io/apiserver/pkg/storage/value/transformer_test.go
@@ -45,7 +45,7 @@ func (t *testTransformer) TransformToStorage(to []byte, context Context) (data [
 
 func TestPrefixFrom(t *testing.T) {
 	testErr := fmt.Errorf("test error")
-	transformErr := fmt.Errorf("test error")
+	transformErr := fmt.Errorf("transform error")
 	transformers := []PrefixTransformer{
 		{Prefix: []byte("first:"), Transformer: &testTransformer{from: []byte("value1")}},
 		{Prefix: []byte("second:"), Transformer: &testTransformer{from: []byte("value2")}},
@@ -64,7 +64,7 @@ func TestPrefixFrom(t *testing.T) {
 		{[]byte("first:value"), []byte("value1"), false, nil, 0},
 		{[]byte("second:value"), []byte("value2"), true, nil, 1},
 		{[]byte("third:value"), nil, false, testErr, -1},
-		{[]byte("fails:value"), nil, true, transformErr, 2},
+		{[]byte("fails:value"), nil, false, transformErr, 2},
 		{[]byte("stale:value"), []byte("value3"), true, nil, 3},
 	}
 	for i, test := range testCases {