2 files changed, 72 insertions, 1 deletions
diff --git a/cli/tests/unit_node/crypto/crypto_sign_test.ts b/cli/tests/unit_node/crypto/crypto_sign_test.ts
index 58107b563..b04cae407 100644
--- a/cli/tests/unit_node/crypto/crypto_sign_test.ts
+++ b/cli/tests/unit_node/crypto/crypto_sign_test.ts
@@ -1,6 +1,9 @@
 // Copyright 2018-2023 the Deno authors. All rights reserved. MIT license.
 
-import { assert, assertEquals } from "../../../../test_util/std/assert/mod.ts";
+import {
+  assert,
+  assertEquals,
+} from "../../../../test_util/std/testing/asserts.ts";
 import { createSign, createVerify, sign, verify } from "node:crypto";
 import { Buffer } from "node:buffer";
 
@@ -9,6 +12,11 @@ const rsaPrivatePem = Buffer.from(
     new URL("../testdata/rsa_private.pem", import.meta.url),
   ),
 );
+const rsaPrivatePkcs1Pem = Buffer.from(
+  await Deno.readFile(
+    new URL("../testdata/rsa_private_pkcs1.pem", import.meta.url),
+  ),
+);
 const rsaPublicPem = Buffer.from(
   await Deno.readFile(
     new URL("../testdata/rsa_public.pem", import.meta.url),
@@ -86,3 +94,39 @@ Deno.test({
     }
   },
 });
+
+Deno.test({
+  name: "crypto.createPrivateKey|sign - RSA PEM",
+  fn() {
+    for (const testCase of table) {
+      for (const algorithm of testCase.algorithms) {
+        assertEquals(
+          createSign(algorithm).update(data).sign(rsaPrivatePem, "hex"),
+          testCase.signature,
+        );
+        assertEquals(
+          sign(algorithm, data, rsaPrivatePem),
+          Buffer.from(testCase.signature, "hex"),
+        );
+      }
+    }
+  },
+});
+
+Deno.test({
+  name: "crypto.createPrivateKey|sign - RSA PKCS1 PEM",
+  fn() {
+    for (const testCase of table) {
+      for (const algorithm of testCase.algorithms) {
+        assertEquals(
+          createSign(algorithm).update(data).sign(rsaPrivatePkcs1Pem, "hex"),
+          testCase.signature,
+        );
+        assertEquals(
+          sign(algorithm, data, rsaPrivatePkcs1Pem),
+          Buffer.from(testCase.signature, "hex"),
+        );
+      }
+    }
+  },
+});
diff --git a/cli/tests/unit_node/testdata/rsa_private_pkcs1.pem b/cli/tests/unit_node/testdata/rsa_private_pkcs1.pem
new file mode 100644
index 000000000..215e5cc51
--- /dev/null
+++ b/cli/tests/unit_node/testdata/rsa_private_pkcs1.pem
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----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+-----END RSA PRIVATE KEY-----