diff --git a/cli/tests/unit/webcrypto_test.ts b/cli/tests/unit/webcrypto_test.ts
index 0828f07162..b1d4e96376 100644
--- a/cli/tests/unit/webcrypto_test.ts
+++ b/cli/tests/unit/webcrypto_test.ts
@@ -690,3 +690,26 @@ unitTest(async function testAesKeyGen() {
   assertEquals(algorithm.name, "AES-GCM");
   assertEquals(algorithm.length, 256);
 });
+
+unitTest(async function testDecryptWithInvalidIntializationVector() {
+  const data = new Uint8Array([42, 42, 42, 42]);
+  const key = await crypto.subtle.generateKey(
+    { name: "AES-CBC", length: 256 },
+    true,
+    ["encrypt", "decrypt"],
+  );
+  const initVector = crypto.getRandomValues(new Uint8Array(16));
+  const encrypted = await crypto.subtle.encrypt(
+    { name: "AES-CBC", iv: initVector },
+    key,
+    data,
+  );
+  const initVector2 = crypto.getRandomValues(new Uint8Array(16));
+  assertRejects(async () => {
+    await crypto.subtle.decrypt(
+      { name: "AES-CBC", iv: initVector2 },
+      key,
+      encrypted,
+    );
+  }, DOMException);
+});
diff --git a/ext/crypto/lib.rs b/ext/crypto/lib.rs
index b0cd7ef061..dcf03d64cc 100644
--- a/ext/crypto/lib.rs
+++ b/ext/crypto/lib.rs
@@ -1603,7 +1603,12 @@ pub async fn op_crypto_decrypt_key(
             block_modes::Cbc<aes::Aes128, block_modes::block_padding::Pkcs7>;
           let cipher = Aes128Cbc::new_from_slices(key, &iv)?;
 
-          cipher.decrypt_vec(data)?
+          cipher.decrypt_vec(data).map_err(|_| {
+            custom_error(
+              "DOMExceptionOperationError",
+              "Decryption failed".to_string(),
+            )
+          })?
         }
         192 => {
           // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
@@ -1611,7 +1616,12 @@ pub async fn op_crypto_decrypt_key(
             block_modes::Cbc<aes::Aes192, block_modes::block_padding::Pkcs7>;
           let cipher = Aes192Cbc::new_from_slices(key, &iv)?;
 
-          cipher.decrypt_vec(data)?
+          cipher.decrypt_vec(data).map_err(|_| {
+            custom_error(
+              "DOMExceptionOperationError",
+              "Decryption failed".to_string(),
+            )
+          })?
         }
         256 => {
           // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
@@ -1619,7 +1629,12 @@ pub async fn op_crypto_decrypt_key(
             block_modes::Cbc<aes::Aes256, block_modes::block_padding::Pkcs7>;
           let cipher = Aes256Cbc::new_from_slices(key, &iv)?;
 
-          cipher.decrypt_vec(data)?
+          cipher.decrypt_vec(data).map_err(|_| {
+            custom_error(
+              "DOMExceptionOperationError",
+              "Decryption failed".to_string(),
+            )
+          })?
         }
         _ => unreachable!(),
       };
diff --git a/tools/wpt/expectation.json b/tools/wpt/expectation.json
index cd3af186cf..a3c4e15cc6 100644
--- a/tools/wpt/expectation.json
+++ b/tools/wpt/expectation.json
@@ -3098,16 +3098,7 @@
         "AES-CBC 256-bit key with mismatched key and algorithm",
         "AES-CBC 128-bit key without decrypt usage",
         "AES-CBC 192-bit key without decrypt usage",
-        "AES-CBC 256-bit key without decrypt usage",
-        "AES-CBC 128-bit key, zeroPadChar",
-        "AES-CBC 128-bit key, bigPadChar",
-        "AES-CBC 128-bit key, inconsistentPadChars",
-        "AES-CBC 192-bit key, zeroPadChar",
-        "AES-CBC 192-bit key, bigPadChar",
-        "AES-CBC 192-bit key, inconsistentPadChars",
-        "AES-CBC 256-bit key, zeroPadChar",
-        "AES-CBC 256-bit key, bigPadChar",
-        "AES-CBC 256-bit key, inconsistentPadChars"
+        "AES-CBC 256-bit key without decrypt usage"
       ],
       "aes_cbc.https.any.worker.html": [
         "AES-CBC 128-bit key without encrypt usage",
@@ -3118,16 +3109,7 @@
         "AES-CBC 256-bit key with mismatched key and algorithm",
         "AES-CBC 128-bit key without decrypt usage",
         "AES-CBC 192-bit key without decrypt usage",
-        "AES-CBC 256-bit key without decrypt usage",
-        "AES-CBC 128-bit key, zeroPadChar",
-        "AES-CBC 128-bit key, bigPadChar",
-        "AES-CBC 128-bit key, inconsistentPadChars",
-        "AES-CBC 192-bit key, zeroPadChar",
-        "AES-CBC 192-bit key, bigPadChar",
-        "AES-CBC 192-bit key, inconsistentPadChars",
-        "AES-CBC 256-bit key, zeroPadChar",
-        "AES-CBC 256-bit key, bigPadChar",
-        "AES-CBC 256-bit key, inconsistentPadChars"
+        "AES-CBC 256-bit key without decrypt usage"
       ],
       "aes_ctr.https.any.html": [
         "AES-CTR 128-bit key",